My Wardrobe, Myself

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:

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.

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:

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.