My Wardrobe, Myself

The intersection of clothing, emotions, and life

It’s time for part two of my personal style update. As a reminder, in my last post, I told you about a style course (now available as a standalone offering) that I took this year to help me better understand and translate my personal style aesthetic. In today’s post, I share some of the exercises I did as part of that course and what I learned about myself and my style as a result. I also outline the challenges I’m still experiencing in dressing in line with the image I want to project. If you love posts that include lots of photos, you’re in luck, as I share many examples here, both of others’ outfits and my own.

Let’s dive in! One of the first things I did was create two Pinterest boards: one that depicted looks I loathe and another that highlighted looks I love. I had fun compiling these boards and enjoyed some good laughs along the way. Interestingly, I found it easier to find examples of outfits that I didn’t like than pinpointing ones that I could readily see myself wearing (especially for my “real life” – more on that later). I think a reason for that discrepancy is that just one garment or accessory could immediately land a look in the dislike category, while pretty much all style elements needed to line up in order for me to classify an ensemble as one that I adored.

Looks I Loathe

Here are some examples from my “Looks I Loathe” board:

looks I love - part one

looks I love - part two

It’s helpful to go beyond just pinning images of what we do and don’t like. If we go a step further and identify the characteristics of these looks that make us like or dislike them, we’ll get clues for what style elements to look out for – and the ones we should try to avoid. Some of the features that I don’t like (for myself) in outfits include:

  • Overly shapeless garments
  • Excessively ripped jeans
  • Puffed sleeves
  • Bell-bottom pants/jeans
  • Partially tucked tops (I know this is trendy, but it’s not for me)
  • Too much going on (patterns, accessories, etc.)
  • Exaggerated proportions, especially accentuating the hip/thigh region (what I’ve always viewed as my “problem area”)
  • Overly tight and/or revealing outfits
  • Brown and tan garments (bad colors for me)
  • Bohemian or “hippy” styles (“boho-lite” is okay sometimes)

Basically, I prefer simpler styles without a lot going on. Some of the looks above are extreme examples of what I don’t like, but they help to illustrate the point. I like to have some shape to my clothing, but I don’t like garments to be too snug-fitting. I sometimes like a bit of distressing in garments, but I’ll leave the excessively ripped jeans to others (I have a few friends who really like that look, and it works for them). I like to do a bit of pattern-mixing sometimes, but I prefer to keep it subtle. As for accessories, I love them, but I prefer to keep it to one or two bold accessories rather than wearing a lot of eye-catching pieces.

It was fun to pull together my “Looks I Loathe” board because I have a strong sense of what I don’t like. I don’t necessarily hate every single outfit that I included on my board (the ones I featured here were among the more extreme examples), but I know that I wouldn’t want to wear any of them myself. Even when some of the style elements I mentioned above are in vogue, I know to avoid them, as I will never be happy with what I’m wearing if it’s too baggy, tight, or “busy,” or if it’s in colors that I don’t like.

Looks I Love

I had to search a bit harder for looks that I loved. Even though I tried a lot of different search terms and phrases on Pinterest, I kept coming up with very similar looks. But once I had pinned a decent number of outfits that I’d be excited to wear, I was shown better options for my “Looks I Love” board. I also reviewed and pinned outfits from some of the stylish women who I follow on Instagram. Eventually, this Pinterest board was much larger than the one I highlighted above. I’m showing more of these examples here, as the rest of this post centers on styles that I do like and on refining my own personal style.

Below are a number of the ensembles that I was drawn to. I did my best to divide them into several categories: black outfits, black and white outfits, denim and black ensembles, looks that featured color, and some miscellaneous looks. This makes it easier to see some of the commonalities among the outfits.

loved looks - black

I love the look of monochromatic black outfits. 

loved looks - black and white

These are some of my favorite black and white ensembles. 

loved looks - black with denim

I love outfits that combine black (and often white as well) with denim. 

loved looks - bright colors

I always like black with bright colors, and I’m now embracing red and deep pink.

miscellaneous loved looks

Here are some more outfits that I would be happy to wear. 

As you viewed the photos above, you probably readily identified some of their common elements. You likely also noticed that they are pretty much diametrically opposed to my “Looks I Loathe” examples. Here are some of the defining characteristics of the ensembles included on my “Looks I Love” board:

  • Monochromatic black outfits or outfits that combine black with one or two other colors
  • Colors besides black include white, cobalt, red, deep pink, and deep green (I also like other jewel tones)
  • Stripes – horizontal, vertical, diagonal
  • Other prints include polka dots, windowpane, and black/white animal prints
  • Long toppers – cardigans, dusters, jackets, vests
  • Long silver necklaces/pendants
  • Asymmetrical details
  • Black boots, peep-toe shoes, and sandals (almost always with some sort of a heel)
  • Simple, streamlined, minimal looks
  • Nothing too tight or binding, but also not overly loose or baggy
  • Incorporate bold, dramatic, or artistic details
  • Simple, streamlined hairstyles
  • Structured handbags

One criterion I used for my “Looks I Love” board was that I needed to be able to see myself wearing the outfit in question. There are many ensembles that I think look great on other people, and some of them are even “my style.” But one of my 2020 wardrobe/style goals is to be physically and emotionally comfortable in all of my clothes. There are certain types of garments that I will never feel comfortable in, including super skinny pants, knee-baring skirts/dresses, and anything that’s too revealing or low-cut. I can often appreciate such elements on others, but when I’ve purchased clothes that fall into these categories, they usually didn’t end up being worn more than a few times (and I was self-conscious the entire time I was wearing them). I definitely dress more conservatively and modestly than a lot of other women, but I’ve made peace with this and will carry on wearing what feels best to me.

My Style Guideposts

In my last post, I wrote about Jennifer Mackey-Mary’s concept of “style guideposts,” which are the three words that best define the way we want to look. These words should complete the sentence, “I want to look…” I struggled quite a bit to identify just three words that best encapsulate how I want to look. The first style guideposts I came up with were “striking, polished, and streamlined,” but that never felt quite right. After revisiting my “Looks I Love” board, I thought that perhaps “dramatic” would be a better word than “striking,” although they are both in the same ballpark. Additionally, I considered that maybe “elegant” might be preferred over “streamlined.” So at least for now, the words that I’m going with are:

  • Dramatic
  • Polished
  • Elegant

Let me explain my choices… First of all, I like there to be some sort of bold, dramatic, or eye-catching element in my outfits, such as a bright color, interesting jewelry, an unexpected style detail, or my signature stripes. It’s also important that I look polished and put-together, which is part of why I don’t like styling details like the “half-tuck.” It just feels unfinished or messy to me. I don’t always feel that way about such looks on others, but it feels wrong on me. The same is true for my natural wavy, frizzy hair texture. It doesn’t feel polished, so I continue to flat-iron my hair to get the straight and smooth look that I prefer. I often like textured hair on other women, but I prefer my own hair to be smooth, as well as uniform in color (which is why growing out my gray hair and sporting a two-toned look for years drove me crazy!).

As for “elegant,” that’s a word that others have often used to describe me and I’ve always been very happy to be referred to in that manner. A lot of the outfits pictured above under “looks I love” could be described as elegant, and I would also classify virtually all of them as dramatic and polished. I feel good about my style guideposts, but if any other words strike you as potentially more appropriate, I’m open to suggestions. I don’t think I need the perfect words – and all of the ones I’ve considered are similar in nature, but it’s possible that I might still refine my words as I continue to work on my style.

Am I Dressing According to My Style Guideposts?

Now that I have my style guideposts in place and have teased out some of the elements I’m looking to incorporate (or not incorporate) in how I dress, it’s time to consider my own wardrobe and outfits. Unfortunately, I don’t have a lot of recent outfit photos to draw upon, as I stopped taking pictures of what I wore back in late 2017. At the time, I was really struggling with my gray hair transition process and menopausal weight gain. I found myself being overly critical of my appearance when I looked at my outfit photos, so I opted to stop taking them.

Even though I finally finished growing out my natural hair and my weight is in a better place (although not back to what it was before “the change”), I didn’t start taking the photos again. Perhaps they served their purpose and I don’t really need them anymore, just like I stopped my longtime practice of tracking garment wears in 2019 and haven’t missed it. But since I did take photos of my outfits for many years, I spent some time the other day looking through all of them. Although there were some cringe-worthy images there (who doesn’t have some of those?), I found a number of outfits that I would happily wear again today. I no longer own some of the items pictured, but I continue to love and wear others years later.

Below is a sampling of the outfits that I still love, divided into several different categories:

some of my favorite black and white outfits

These are some of my favorite black and white outfits (2016-2019).

some of my favorite black and cobalt ensembles

I love to pair black and cobalt together (2012-2017 outfits). 

favorite outfits including black and color

Some of my favorite outfits including black and bright colors (2015-2019).

miscellaneous loved looks of mine

These are some more of my favorite looks from 2016-2019.

Many of my outfits are more casual than the ones from my “Loves I Love” board, but my life is generally quite casual (especially lately). It wasn’t easy to find dressed-down images that struck my fancy when perusing Pinterest, plus I think my style aesthetic skews dressy anyway, which has often been a problem for me. I’ve never embraced the ultra-casual Southern California way of dressing, as I don’t feel emotionally comfortable wearing the tank top, shorts, and flip-flop ensembles that are so common here. I much prefer to wear heels, a third piece, and bold accessories.

I think that most of my outfits pictured above line up with many of the characteristics I highlighted from my Pinterest inspiration looks. However, I’d like to bring in more color (including red and deep pink), some monochromatic black looks, and additional dramatic and artistic details. Although I love black, I rarely wear all-black looks, but I could see myself doing that more often moving forward. I think many of my outfits need a bit more of an “edge” to them, but that can be challenging in ultra-casual situations.

My Main Style Challenge

This brings me to my main style challenge… Jennifer Mackey-Mary specified that everything we wear should be in line with our style guideposts, including our workout wear, lounge wear, and pajamas. I had a huge “aha moment” when I heard her say this! This is the key to why I’m often unhappy with my style. While I think that nearly all of my “out-and-about” outfits could be described as dramatic, polished, and elegant, the same cannot be said for much of what I wear at home and when I’m exercising (my walks and when I used to go to the gym pre-Covid). Jennifer did say that we don’t need to hit all three guideposts every single time, but she stated that we should aim for at least two of them. Her style guideposts are “fun, current, and polished,” which I think are easier to meet in casual ensembles than the guideposts I have chosen, but I don’t want to let that stop me.

I’m happy with my guideposts and I’m usually satisfied (or even pleased) with what I wear when I’m out and about. However, out-and-about occasions have become even rarer for me than they were before the pandemic hit in March. So I really need to work on having the outfits I wear for the main occasions of my life meet my style guideposts. I don’t think it’s easy for a workout outfit or pajamas to be dramatic, but perhaps that could be accomplished with bold colors and patterns, as well as some interesting details. I think that much of what I wear at home now could be defined as elegant and polished, so maybe that’s enough. This is all still a work in progress…

Conclusion – and Your Thoughts?

I’m going to be mindful of my style guideposts whenever I get dressed. I’m going to ask myself if what I’m wearing is dramatic, polished, and elegant. Does each outfit hit at least two of these criteria? If not, what could I change in order to better match up with the way I want to look? It may be as simple as switching out one piece, or I may have to scrap the whole ensemble and start over. I don’t tend to wear accessories or jewelry when I’m at home or exercising, so it will be a bit more challenging to live up to all of my style guideposts, but I’m going to do my best and see how it goes.

I think it’s important to feel good in what we’re wearing regardless of where we are and what we’re doing. Jennifer Mackey-Mary says that the biggest mistake that women make is separating the way they want to look from the way they actually live. I definitely did that for many years by prioritizing my out-and-about outfits and leaving what I wore the rest of the time (the majority of my life!) as basically an afterthought. Then I wondered why I felt so dissatisfied with my style! Well, now I know better, so I can do better. Onward!

As always, I’d love to get your thoughts on what I’ve written about in today’s post. Feel free to comment about my style journey or your own. If you’ve identified your own style guideposts, please share them. If you’ve taken the time to create “Looks I Love” and “Looks I Loathe” boards, what are some of the common elements of each? How would you like to change your style moving forward? What challenges do you have in dressing the way you want to look? How has the current situation affected your style and what you want it to be? I look forward to hearing from you and I wish you a wonderful weekend.

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28 thoughts on “Personal Style in 2020 and Beyond

  1. Julia says:

    Oh, how I can empathise with the phrases “my style aesthetic skews dressy” and “separating the way they want to look from the way they live”. I am very petite and have always been drawn to ‘dressy’ clothes as I felt they suited me better, which was fine for my long working life and accompanying lifestyle. Come retirement, a move to another country, a different climate and a very rural environment and I was lost!

    A lot of work later, with your help and ‘The Vivienne Files’ for colour inspiration, I am finally coming to terms with the fact that I no longer need smart clothes (and confinement has shown what a small wardrobe I actually do need!) and instead work on looking ‘casual but polished’. And pep things up a bit with the accessories I have collected over the years but barely see the light of day.

    Your ‘Looks I Loathe’ gave me some smiles; what were they thinking. As to the ‘Looks I Love’ I immediately saw you in a lot of them, and honestly you look every bit as good. I think you had already found your style and this just confirmed and refined it. However, I would love to see you with the hair and outfit in the 6th monochromatic black photo!

    1. Debbie Roes says:

      I’m glad that I could play some role in helping you to cultivate “casual but polished” style, Julia. The Vivienne Files offers a lot of wonderful advice, especially about color. Thank you for your kind words about my style and outfits. Yes, I think that doing this exercise helped to confirm that I’m on the right track. Now it’s all about refining and making sure that what I wear for my entire life is in line with my style guideposts. I love that 6th monochromatic black look, too! That’s The Accidental Icon ( and she’s fabulous!

  2. Krissie says:

    I had to smile and agree completely with you on the loathe looks board…but then different strokes for different folks and all that… I think JMHO is that you look particularly stunning in those shades of pink plum and purple. I think you look amazing in those colours and they “light”you up!
    Looking at some of the photos I recognised a few instagramers that I follow. Susan Une femme is a lady whos style I particularly resonate with and like very much. When I first came across her boards, I immediately saved her photos and tried to emulate her style as its the closest to mine I like to think. A while ago she changed up her colours which I didn’t like as much but I still enjoy her “style”and try to model myself on that.

    Now with the situation as it is, I feel as if it doesn’t really matter what I wear inside, and tend to stick with Pj’s and lounge wear, which as long as its comfy I don’t care. We are having a second wave here and things are a bit depressing, so clothes are my least priority. Once all this goes back to normal, hopefully my clothes mojo will return. Another thing is that our shops on re opening are still selling last seasons clothes and not any warm ones as its winter here, which is a bit odd, so like most women here fashion and clothes here are taking a real back step and when changing rooms aren’t open makes shopping harder. Buying online would be great if all the brands had a standard sizing policy and sadly from what I gather a lot of ladies here prefer to buy in a shop and not online because of problems taking or sending the clothes back when they don’t fit.

    as usual a great and much looked forward to post!

    1. Debbie Roes says:

      Thank you for your compliment about me in pink plum and purple, Krissie! I love those shades, but that can be difficult to find sometimes… I resonate with Une Femme’s style, too, but also more before she changed her colors (but the important thing is that she’s happy). Yes, this is definitely a difficult and depressing time! I’ve felt like I lost my style mojo, too, which is why I’ve been working on it more lately, especially in terms of what I wear at home. But I wasn’t happy with what I was wearing at home. If you are – or if it’s just not that important right now, that is of course okay. Online shopping can be quite challenging, especially in regards to sizing, but sometimes it’s hard to discern colors and fabrics, too. I do shop online out of necessity (particularly lately), but I find it to be a frustrating experience rather than a relaxing or fun one (which shopping in stores used to be). I hope that brick and mortar shopping won’t go away and I hope we will be able to enjoy it once again (and not in the too distant future!).

  3. Sally says:

    Hi Debbie

    I think your like and dislike boards definitely align with your style aesthetic and the images that you like are similar to your favourite photos of yourself, although as you said, some are a bit more dressy than your lifestyle. I think the 3 words you have chosen describe your style now and over time if your style evolves, so too will your style words.

    As the majority of your time is spent at home or going for walks, it is important that your loungewear/sleepwear and activewear are in line with your style guidelines. The first thing is to buy clothes specifically to wear for those activities and not just wear things that are too old and worn out for out and about clothes, as that will not make you feel polished or elegant and I know you have started to do this.

    I think it would be easy to buy clothes in these categories in-line your style guidelines.

    For loungewear/sleepwear, think of comfortable fabrics with stretch like bamboo, jersey and modal, with elegant draping and in your dramatic colours black, cobalt, red, stripes. Here are some examples of bamboo clothing in-line with your style guidelines:

    Tops in black, cobalt, black & white stripe, red & black stripe:

    Pants in black or cobalt:

    Wraps/cardigans in black, blue or red:

    Maxie dress in black & white stripe or red & white stripe:

    PJs red or black, or get both, then can mix tops & bottoms as more dramatic:

    Amazon carries slippers in dramatic blue, red or black, as well as in dramatic snow leopard and zebra prints (brands: L.A.M.B., EMU, UGG, Old Friend, and LAVRA).

    Similarly with your activewear, you can find clothes that meet your criteria. Here are a selection of examples from Lululemon of red, blue and black & white jackets, tees, black pants and sneakers that will make your activewear outfits look polished and dramatic:

    Red Jackets:

    Black & White Jacket:

    Blue Jacket:

    Black & White tees:

    Red Tee:

    Black Pants:

    Red, black & white sneakers:

    I hope this helps to give you some ideas, as I think this is the area you need to focus on, so that the clothes you spend most of your time in make you feel good and look polished, elegant and dramatic.

    Regards Sally

    1. Debbie Roes says:

      Sally, you’re a superstar! I really appreciate all of the wonderful links you shared (I had to remove the Amazon ones, as they were showing big pictures and I couldn’t figure out how to get it to stop doing that!). I especially love the Yala Designs items! I had never heard of that brand before, but it’s definitely one I will keep on my radar screen. Your tips are great, too. I really think the disconnect I’ve been feeling has had to do with paying too little attention to what I wear for the less dressy parts of my life (which is actually MOST of my life!). I agree that if I pay more attention to my loungewear/sleepwear, I will feel much better, and it doesn’t have to be THAT hard, either. I’ve already noticed that when I wear my preferred colors and patterns, I feel a lot better, so I’m not going to compromise there anymore. Fortunately, the colors I like most are readily available, as your links prove. I’ve gotten a lot better at not “downgrading” clothes for at-home use, unless they are still in good shape and things I enjoy wearing. It’s important for us to feel attractive and stylish wherever we are, particularly for those of us who spend a lot of time at home. I’ve already noticed a difference, and when I need to add new items, I will check out the links you shared. I was very excited to see cobalt joggers (well, maybe they were more navy, but still a nice blue!), but I do worry about the inseam length. People always tell me I’m lucky to be so tall, but it certainly makes shopping more challenging!

      1. Sally says:

        Hi Debbie,

        Glad you found my links helpful to show that there are plenty of clothes out there in your style for loungewear/sleepwear and activewear, it’s just a matter of making the effort and not compromising, if you want to look and feel good, in all aspects of your life.

        As you know, I too have problems finding full length pants that are long enough for me, as I am 6” tall with long legs. When I was growing up there was nothing worse than wearing full length pants that were not long enough for me, as I used to get comments like, “Have your pants shrunk in the wash?”

        Therefore, now I prefer to wear ankle length or 7/8th length pants, as they are much easier to find. They hide the widest part of your calf but show off the slimmest part of your leg and end a couple of inches above the ankle bone. These are always chic, think of Audrey Hepburn. They should be slim fit and tapered to follow the natural shape of your leg, make sure they are fitted at the hip and thigh. The most important thing is to look intentional, like your pants are supposed to be a little short. For my out and about pants I wear bengaline fabric as very comfortable, stretchy and slimming.

        It is easier to find full length loungewear/sleepwear pants that are long enough to wear at home with slippers, than it is to find full length out and about pants that are long enough to wear with heels.

        For my loungewear/sleepwear, I wear bamboo fabric as very soft on the skin, breathable, comfortable and stretchy. I have found full length relaxed pants that are long enough to wear at home with slippers.

        Glad you liked the link to the jogger style bamboo pants. Don’t worry so much about the length of these on you. If you wear slim fit or jogger style loungewear/sleepwear bamboo pants at home, then if they are ankle length on you, they still look good and intentional and you can wear them with socks and slippers to keep feet and ankles warm.

        However, I think relaxed or wide leg pants must be the correct full length with slippers because if they are ankle length, they just look like you couldn’t get pants long enough or they have shrunk in the wash.

        Happy hunting.

        Regards Sally.

        1. Debbie Roes says:

          I had the same experience as you did with pants being too short while I was growing up (I’m 5’10” but I’m pretty much all arms and legs!), so I am hyper-sensitive to that issue, too. I initially resisted ankle pants, but now I wear them all the time. As long as shorter pants look intentional, I’m happy with them now. I agree that they look better tapered, even though there is a current trend of wider-legged cropped pants (I don’t like those on me). I hadn’t heard of bengaline fabric, but after looking it up, I realize that I like and wear pants made with it 🙂 I don’t think I have anything made with bamboo fabric, but it sounds like a good choice for me. The only potential issue with the joggers being too short is that I have “meaty” calves and the elastic could potentially be too tight if the pants are significantly too short on me. During the cooler months, I always wear socks and slippers at home, but now that it’s warm here (opposite seasons from you…), I mostly wear Hoka Recovery Slides, as they are comfortable and offer arch support and shock absorption (we have ceramic tile flooring). And of course, they are black! Thanks again for all of your great tips and recommendations!

        2. Sally says:

          Hi Debbie

          Bamboo clothing is good for eczema and allergy sufferers, it is extremely smooth and soft, it is breathable, lightweight and can help regulate body temperature, so good for menopause flushes. It absorbs moisture keeping your body fresh and dry.

          The bamboo clothes have some spandex in them too, so that they keep their shape.

          I found Yala designs US website for you because I know you too have issues with skin sensitivity and dyes. I have not bought from them, as I buy from AU websites.

          Here is information from their website regarding their materials used, as I know this is important to you & a link if you want more info:

          “Take comfort in how our clothes feel, look and are made. We use low impact and azo-free dyes on our garments. This reduces the toxins in the environment and prevents them from being next to your skin. We believe in designing garments that will stand the test of time. We create artfully simple, timeless style made with excellent construction and premium fabrics.”

          I suggest you start with adding some of their stripe tees to your loungewear/sleepwear wardrobe, as easier to fit than pants and they have 20% off your first order and if you like them, then buy more bamboo clothes.

          Hope this helps.
          Regards Sally

        3. Debbie Roes says:

          I really appreciate all of the great information you’ve sharing in response to this post (and many other posts), Sally! It was very kind of you to search out links for me and to find a good source for bamboo clothing in the U.S. I love the look of the Yala Designs clothes, and it’s wonderful that they are also environmentally friendly! I definitely plan to order some pieces from them in the near future. I’m sure others who are reading will also benefit from some of the links and resources that you shared, too.

  4. Nikki says:

    I think you look great. It’s fun to analyze your personal style. I prefer flats with my outfits. Probably self-conscious of my height. I like tight pants but try to balance the top. I don’t wear the same exact outfit twice. I switch the concept using belts, hats and shoes. I agree with the no/go on bell bottoms. I don’t prefer the look either. Enjoy your post.

    1. Debbie Roes says:

      It sounds like you have a good sense of your style, Nikki. It’s helpful to know our style preferences. You must be very creative not to wear the same outfit twice! Accessories can help a lot to switch up our looks, such that it’s not even obvious to others that we’re wearing the same garments. I’m glad you liked this post!

  5. Katrina B says:

    I have long thought that you had a very clear idea of your style (even if you didn’t know it), based on the consistency of silhouette and color of the items in your wardrobe over the years. But it can be a wonderful confirmation when you discover that you are already wearing your best style. Even if you stray occasionally, which is actually OK because you never know – the latest fad might fit in perfectly with your own style. Anyone seeing you in your black and white or black and brights with geometric lines would agree that Dramatic is a good description. I love that you’re looking for ways to incorporate your guideposts into workout clothes and pajamas. It makes so much sense to feel good about your outfit all day every day instead of just the rare occasion when you go out.

    I LOVE the word Polished, it kind of encapsulates a feeling I had but couldn’t describe. Some years ago I loved soft, loose, natural looks and thought with my at-home lifestyle and wavy gray hair that would be perfect for me. But instead of looking like an off-duty model I looked like a mountain of poorly-fitting clothes and my curly, uncontrolled hair actually aged me. That was when I fell down the rabbit hole of style types, color analysis, etc and came out as a Dramatic Classic (which is a quite challenge with light spring coloring!). Polish is very much an attribute of the Dramatic and the Classic, and once I started wearing more structured clothes and blowing out my hair, I finally recognized myself in the mirror. And I certainly do agree with you that it is hard to reconcile a dramatic, polished style with a very relaxed life in a very casual city. People here wear shorts and baseball caps to the opera.😢

    Well I had quite a time with the Love/Loathe exercise. First, I was having trouble with “loathe” because it seemed too strong and I felt like I was insulting people’s photos on Pinterest! 🤣 I decided it was easier to think about whether I Would or Would Not wear the looks. It was easy to pin things to the two boards, but for me, surprisingly difficult to analyze the differences between the two. For example I could say that I love florals, but then I have equal numbers of floral looks on both boards. It comes down to color and size of the flowers, apparently! I like man-tailored trousers and oxfords but only in some outfits. And some silhouettes that I love and regularly wear can’t even be found on Pinterest (I don’t exactly keep up with current fashion). Still it was a very fun and helpful exercise and confirmed that I definitely don’t need to branch out into puffy sleeves or skinny jeans.

    I am reconsidering my words/guideposts – formerly Comfortable, Confident, Creative – because after reflection I agree that comfortable is a given and I don’t need it as part of my style description. I might try Polished or possibly Refined.

    Thanks for another fascinating post and for your generosity in sharing so much.

    1. Debbie Roes says:

      I think you’re right that I knew my style, Katrina, but I just wasn’t translating it to the more casual areas of my life, and that’s why I felt discontented. I need to incorporate more of the dramatic in what I wear at home, including in items like pajamas and exercise wear. It’s interesting how sleepwear colors are often more muted, but that’s just not going to make me happy, so I have to be diligent in searching out what will spark joy for me. I fit into the Dramatic Classic category (Kibbe, right?), too. I think there was also a straight Dramatic category and that was a bit edgier than what I usually prefer, but Dramatic Classic seemed dead on. I can imagine trying to accomplish this look with light spring coloring would be challenging! So you get it about the hair? I’m glad that someone with a similar aesthetic understands. So often the advice is to “embrace our natural texture,” but that just doesn’t make me happy. In my heart, I have long, sleek, silver hair, but it DOES take more work to achieve that. I’m willing to do it, though. So you feel my pain about that and about living in an ultra-casual city… I’m sure people wear shorts and baseball caps to the opera here, too, but I can’t verify that since I’ve never gone.

      Yes, “loathe” is an extreme term. I see that Jennifer has toned it down to be “can’t stand” in her most recent iteration of the course (but that’s still a pretty extreme expression). I did feel a bit bad displaying my “loathe” photos on the blog, but I know that there will never be a style that’s everyone’s cup of tea. As I said, I can often appreciate styles on others that I would never wear myself. Different strokes… I agree with you that “comfortable” is pretty much a given. It wasn’t always for me, but it definitely SHOULD be (and will be from now on!). Polished or refined both seem like good substitution words for you. They are very similar but evoke a bit of a different message. You can always play around with words and switch them out as necessary. Glad you liked this two-part series and it made you think and explore 🙂

  6. Jenn says:

    As someone who has also struggled to nail down her personal style, I immensely enjoyed your most recent post.

    After reading it, I scrolled through Pinterest and noted details that don’t work for me—some of which you had listed. Then I focused on items I’d pinned. Like you, I prefer simpler styles that have some shape to them but aren’t too snug. And my hair is also frizzy and wavy, but I feel most like “me” when I let it do its thing.

    For reference, I’m a (Kibbe) Soft Classic. An experienced “Color Me Beautiful” consultant spent hours trying to determine whether I was a “Light Spring” or “Light Summer.” She finally settled on “Light Spring.” I know myself well enough now to say that if I fit into any CMB category, it would probably be “Light Summer,” but my most complementary colors are the ones those two seasons have in common. And I appear drab in colors that are too soft and overwhelmed by shades that are too bright.

    Elements I love in the looks I pinned:

    • Textured or open-stitch sweaters
    • Outfits with low to medium contrast
    • An effortless appearance
    • Soft fabrics
    • Not too structured or “business-like”
    • Nothing too tight or binding, but also not overly loose or baggy
    • Colorful solids or fun patterns, like asymmetrical polka dots
    • Tops in light to medium neutral or cool shades
    • Solid, neutral bottoms
    • Skinny, slim, or boot-cut pants
    • Boots, sandals, and flats or low-heels
    • Long pendants
    • Simple basics, “seasoned” with subtle bohemian, vintage, embellishment, and/or playful details

    Jennifer Mackey-Mary’s podcast is by far the best style podcast I’ve come across, and I like the idea of selecting three words as “Style guideposts.” (I love the three you chose, by the way!)

    As you know, I recently completed an online class with Brenda Kinsel. In addition to the “Conditions of Satisfaction” (mentioned in my comments on your previous post), we each concocted our own “Style recipes.” Here’s what I came up with for me:

    • Soft yet resilient
    • Refined casual (I might ditch this ingredient because I’m NOT always either or both!)
    • Intentionally effortless
    • Subtly feminine
    • A whisper of whimsy

    I look forward to hearing more about how you use your guideposts going forward!

    1. Debbie Roes says:

      Jenn, I was looking forward to your comment, as I know you’ve also been doing a lot of style exploration. Thanks for sharing so much about your own style and what you’ve learned and decided for yourself. You’re lucky that frizzy and wavy hair feels like you… I would be saved a lot of time if that were true for me! I think that I’m a Kibbe Dramatic Classic, which would make sense. What you describe sounds very much in line with Soft Classic. It sounds like it took some time for you to figure out your best colors, but you appear to have that very well established now, which is great. The CMB categories can be very difficult to nail down. I’m not sure what I am in the classification. I’ve been told that I’m a Winter, but I’m not sure which type of winter? The fact that I have brown eyes makes it more challenging, and my hair color has changed a lot. I’ve toned down my colors a bit (and embraced the reds and pinks more), but I mostly wear the same colors I did when my hair was dyed.

      I love Jennifer’s podcast, too! Today it was all about curly hair, so you may find it interesting and helpful. I love the idea of a “style recipe”! Yours sounds perfect for you. Maybe you just need to tweak “refined casual” to better describe what you were trying to convey, or maybe you’ll be just fine with the other four “ingredients.” Whimsy is a good thing! I’m sure I will write more about my guideposts. I’ve already been considering my at-home wardrobe and perhaps purging anything that isn’t in line with dramatic, polished, and elegant (or at least two of the three).

      1. Sally says:

        Hi Debbie

        Imogen Lamport has just released a new bog post and video on
        “DEFINING YOUR WHOLE-LIFE STYLE RECIPE”, which is very timely for the discussions on this post:

        She gives a very good example of people she sees out on her daily walks round the park, where she sees the same people and has started “naming” these people using something that identifies them, as she doesn’t know their name. In essence, shes created a style recipe for each of these people that she passes in the park:

        “If you translate this to a style recipe, it’s a tool that helps you tell the world something about you.
        If you were walking around my park, what would you like me or others to pick up about you?  
        What’s your personality?  What do you want people to know about you?  Who are you and how can you express that through your image?
        Given that your image is communicating without you saying anything, what it is that you want it to say?
        One of the things I think is important is to ensure that your style recipe works for your whole life, not just work, but for everything you do.  Who are you at your core and what do you want people to know?”

        That’s why it’s important that you also review your activewear (see my earlier Lululemon links and comments), so that when you go out for your daily walks, the clothes you are wearing are in line with your style recipe of dramatic, polished and elegant, so that is how others would describe you.

        Regards Sally

        1. Debbie Roes says:

          How very timely this Imogen Lamport post is… Thanks for sharing it, Sally! Her idea of a “style recipe” sounds quite similar to what Jenn learned about in her class with Brenda Kinsel. I definitely want people to see dramatic, polished, and elegant when they see me, even if I’m ultra-casual going for a walk. This will take a bit of “tweaking,” but I’m glad to be thinking about this now. When it comes to activewear, a lot of it will be about the colors, patterns, fabrics, and silhouettes that I wear. I’m going to be a lot more mindful about what I buy for ALL areas of my life now. That means no more “cutesy” pajamas and no more muted colors, among other things. Thanks for all of the help you’ve offered in response to this post!

  7. Sue Barlow says:

    Hi Debbie,

    Another fascinating article. Although we have totally different colouring and body shapes (I am long in the body) your comments are very relevant. You have helped me realise what I like in clothes and what I dislike on me. Now when I look at fashion pictures I try to think would I wear it? Usually the answer is no. Whoever thought cropped flares were a good idea?

    Simple is definitely one of my words and I am trying for elegant.

    I am now going to upset everybody and say I really dislike stripes, especially on me. I look like a wrestler! Wrap tops have the same effect. That said I do have one striped top which I do like.

    I love you in your black and cobalt blue outfits.

    1. Debbie Roes says:

      I’m so glad you found this post helpful, Sue. There are lots of styles that we can appreciate on others, but we need to ask ourselves if we would wear similar styles ourselves. I think this next step is often missing, especially when people want to look current. We can still look current if we honor our style guideposts, but certain styles won’t be a good fit (cropped flares aren’t for me, either!) and it’s important for us to recognize that. No worries if you don’t like stripes! They aren’t for everyone, but it’s good that you have one striped top that you like. Thanks for your compliment on my black and cobalt outfits. I’ve loved that combination for years and I’m sure that will continue to be the case.

  8. Mo says:

    Liked this very much.
    I can’t quite pick 3 words but I have 3 general overall bases I like to hit. Looking proportional/balanced/cohesive – at ease/effortless/unfussy – eye catching/memorable/visually striking. The last part I can’t quite verbalize right but I know it when I’m wearing it. Not overtly “look at me!!” but not melting into the background either.
    I agree that hitting guideposts in all areas is important instead of just focusing on ‘out and about’. Most of our lives these days are in categories other than ‘out and about’ anyway!
    My newest struggle is fitting my style around the changing 50 year old body. Some more fitted or skin baring styles aren’t feeling or looking as good as they once did. But I don’t want to dress overly modestly, which is not my personality, just to adapt to a squishier middle, etc. Finding that new edge for my age.

    1. Mo says:

      Maybe better words would be streamlined and insouciant. Again that last one escapes me – some sort of celebrating the feminine but with an edge, not as a sexual come hither.

      1. Nikki says:

        Avant-garde might work.

    2. Wendy says:

      The designers that come to mind with your description are Crea Concept, Rundholz, Grizas, Monies Jewelry? Am I on the right track? Or maybe more simplier cuts like Eileen Fisher and Everlane.

      1. Mo says:

        I think I’m doing a terrible job explaining. If there isn’t a bit of edge, or a figure highlighting component of some sort, it falls flat for me and feels too pedestrian. Don’t get me wrong, I wear such outfits all the time in my mountain town to the grocery, etc, but I would not describe them as aspirational in any way, merely functional, and they feel a bit ‘off’ and almost frumpy. It can be hard to live a casual life like Debbie describes, and have your outfits feel elevated without being too dressed up for your surroundings.

        1. Debbie Roes says:

          I totally get what you’re saying here, Mo, especially since I’m very familiar with where you live and how most people dress. It’s similar where I am, although the type of casual vibe is somewhat different. I’m really trying to figure out a way for my more “functional” outfits to still be in line with my style statement, but it has been challenging. I think that I continue to look more dressed up than a lot of people in my neck of the woods, but the disparity is much less than it used to be. Still working on it…

    3. Sally says:

      Hi Mo

      This blog post & video from Imogen Lamport might help you to define your style recipe:

      Hope this helps
      Regards Sally

    4. Debbie Roes says:

      Great to see you comment here, Mo! Knowing you and having seen many of your gorgeous outfits, I think you’re on the right track with the worse that you mentioned. I definitely see “edgy” in a lot of what you wear, too, especially for your more dressed up looks, but even when you’re dressed down, you usually seem to have at least one edgy element in the mix. I had to look up “insouciant”… but I like that word for you. It can be challenging to come up with 3 style guideposts. It definitely took me a while to settle upon mine, so take your time. I like that others are weighing in with some possibilities for you to consider, but I know it can be difficult to explain visuals with words.

      I feel you with what you wrote about fitting your style around a changing body (happy belated birthday, by the way, and you do NOT look 50 at all!). I lost my way for a couple of years with my body changes, but I’m finally settling in on a happy medium. I used to always wear very fitted clothes and now I’m more into things “gliding” over my body more so as not to show off the “squishiness” that seems to come with menopause. No, I don’t see you dressing overly modestly, but I think you’ll be able to find a way to still have that kind of “rock and roll” edge that you do so well even if you’re not as lean as you once were (although last I saw you, you still looked amazing in my eyes!). It may take a bit of time, but I’m confident that you will get there.

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