My Wardrobe, Myself

The intersection of clothing, emotions, and life

I started the practice of keeping an outfit journal almost ten years ago as one way of addressing an ongoing style rut. Since that time, I have periodically returned to this practice to help increase my awareness of what does and doesn’t work for my personal style. This awareness helps me to create better outfits, and it also assists me in planning my future purchases.

As I jot down my thoughts in each day’s entry (which includes an itemized list of what I wore, where I wore it, my thoughts on the outfit, and a rating on a scale of one to ten), I receive some powerful “aha moments.” But it’s when I go back and review several months’ entries that I gain the most insights. As the warm weather season is finally drawing to a close where I live, I decided to reflect upon what I wore over the past four or so months to see what I might learn.

Outfit Journal Lessons Learned

What have you learned about your wardrobe and style this year? 

Today’s post is part one in a two-part series, in which I encapsulate my key lessons from dressing for summer and fall 2023. I’ll look at what my favorite outfits had in common, as well as what didn’t work in my lesser-loved looks. Then in part two, I’ll review some additional lessons that I learned from reviewing my summer and fall outfit journal entries. I’ll also list out the action items that I’ve outlined based upon the comments I made regarding my warm weather looks.

What Worked in My Warm Weather Outfits

Let’s begin on a high note and look at what my favorite ensembles had in common. These are outfits that I rated most highly, usually either a nine or a ten on a scale of one to ten.

Black and Silver for the Win

My favorite outfits all had black as the main neutral. While I also wear other neutrals (most notably navy), I was happiest when my outfits were grounded in black. In fact, some of my most loved ensembles consisted of two black pieces with one bright or printed item, which I feel is a simple and elegant look. As for my jewelry, I prefer silver pieces that incorporate black in some way, either with onyx stones or black leather or fabric components.

I’m sure it’s not surprising that many of my favorite garments and jewelry pieces are black. Interestingly, this hasn’t changed either with age or after transitioning to my natural hair color. That said, I probably don’t need more black clothing items or accessories, as I already own a large number of them. I need to just focus on wearing and loving what I already have until I need to replace a worn-out item or if I happen upon something I love that’s dramatically different from my existing pieces.

Winning Outfit Formulas

I mentioned the “two black pieces with one bright or print” outfit formula, but I noticed a few others that worked well for me, too:

  • I enjoy wearing printed pants with solid tops, or vice versa.
  • I also enjoy having one brightly-colored item or one printed item in an outfit. This is true regardless of whether or not the main neutral of the look is black.

If I’m going to wear light or bright pieces, I prefer to have them be on the top half of my body. Two exceptions to this general guideline are a pair of purple cropped pants and a pair of light-wash cropped jeans that I enjoy wearing. However, I usually like to wear dark neutral items on my lower half (often black, navy, or dark-wash denim), and the printed pants, skirts, or dresses that I wear tend to be grounded in black.

  • I liked my pants outfits a lot better than the dress and skirt looks that I wore this summer.

For the most part, my dress and skirt outfits felt more conservative and “dressy,” so I started reserving those ensembles for wearing to church. Although I don’t need to dress up for the informal church that I attend, I don’t feel out of place stepping up the formality of my outfits in that environment. However, I don’t have many dresses and skirts that I love at this point, and I mostly stick to wearing pants these days. I’ll cover my current issues with dresses and skirts below in the section on what’s not working.

I Prefer Three-Piece Ensembles

My outfits that included a third piece were invariably rated higher than those that consisted of just two items. There are many reasons why such looks scored higher in my esteem, including better proportions (I’ll get to that topic later), more visual interest, feeling more put-together, and having increased coverage (which often helps with my emotional comfort).

Unfortunately, many summer days are too warm for wearing a third piece, so I had to stick with wearing just a top and a pair of pants (or less often, a skirt or dress) those times. In such instances, I felt more “complete” when I incorporated a necklace into the ensemble. A scarf would have also worked, but it’s generally too warm for even a lightweight scarf on summer days. I’m going to concentrate more on wearing scarves in the winter and spring months, when it tends to be much cooler (although there can be a lot of unseasonably warm days). Of course, I usually wear a third piece then, too, so my cool weather outfits are overall far less challenging for me.

My Favorite Fits and Silhouettes

I tend to stay fairly consistent in terms of the silhouettes I wear and how I like my clothes to fit. I like for most of my garments to be fitted but not tight. This is basically true for everything that I wear, whether it be tops, pants, dresses, skirts, or toppers. I haven’t gotten on board with the more recent trends of wide-leg pants, boxy tops, and billowy dresses and skirts just yet – and I may never embrace them. I’ve tried such pieces on, but I haven’t felt attractive or fab. I don’t like my clothes to be snug-fitting, either, but I do like what I consider to be a “streamlined” fit.

I usually wear knit pieces with some stretch to the fabric (which helps things stay in place better), but I prefer woven pants for the structure that they provide for my larger bottom half. Part of why I love Athleta pants so much is because they specialize in “stretch wovens,” which include a good amount of Spandex. The fact that almost all Athleta styles are offered in tall sizes (they offer petite and plus sizing, too) has contributed to my loyalty to that brand. A big bonus is that they have many “city pants” that don’t look like athleisure pieces at all.

The More “Favorites” in an Outfit, the Better

As I reviewed my outfit journal from the past four months, I highlighted which pieces in each ensemble were among my favorites. Not surprisingly, I found that the more “favorites” were included in an outfit, the more likely that look ended up being scored as an “8” or higher. However, just one fussy or substandard item could easily sink what might have otherwise been a stellar outfit.

I usually write in my outfit journal before I change into my at-home clothing. That way, if I single out a given garment as either ruining or downgrading a look, I’m able to easily try to swap in another item that might work better. While it used to be pants that gave me the most trouble and led to my disliking a lot of my outfits, it’s more likely these days that my top is the “troublemaker.” But fortunately, my outfit journal notes show that I usually have at least one or two alternate pieces on hand that I can swap in to create a higher-rated look the next time around.

What Didn’t Work So Well in My Summer and Fall Looks

Now let’s look at what didn’t work so well in my warm weather outfits, and what some of my lower-rated ensembles had in common. I already mentioned a few problems in the section above while discussing my “wins,” but I want to delve deeper here.

Problematic Tops

As I stated in the previous section, my tops have been more problematic for me lately than my pants. The quality of knit pieces has declined in recent years, but I have such difficulty finding woven tops that fit me well that I continue to stick with knits. My outfit journal has helped me to pinpoint what some of the problems are with my tops, beyond the questionable quality that’s hard for any of us to fully avoid in this modern “fast fashion” era.

Here are some of the issues that I’ve noticed with my tops:

  • Tops that don’t include any elastane or Spandex in the fabrication tend to stretch out and become shapeless rather quickly. Conversely, tops that include even a small amount of Spandex in the mix are usually less fussy and stay in place better. Unfortunately, I found myself owning quite a few tops this summer that were not stretchy and were indeed fussy. That was a big reason why I let go of a relatively large number of tops during my recent closet audit (which I’ll share more about soon).
  • Low scoop-necks and low V-necks don’t look good with my proportions. I have a short torso, which leads to a lot of tops being too low-cut on me – and why I often need to shorten the straps on sleeveless tops and dresses. While I don’t plan on buying tops with low scoop or low V necklines in the future, I’ve been able to “rescue” some of the ones I have by filling in the neckline with a short pendant or necklace. The necklace helps to lessen the “too low-cut” effect by covering up some of the expanse of skin the low neckline creates.
  • Many tops are either too short or too long. The current styles of tops tend to be too short for my personal preference. Even though I’m short-waisted, I’m still tall and need more fabric at the hemline than what tends to be available. Unfortunately, however, many of the longer tops on offer can be too long, as they stop right at the widest point of my body, which is my lower hip area (I have an X body shape per Imogen Lamport’s system). So, I need to find that “Goldilocks sweet spot” for top length, which has become increasingly difficult, especially since many of the current top silhouettes are not to my liking, leaving me with fewer choices.

Less-Than-Ideal Proportions

I wrote an entire post on this issue, so I won’t belabor the point too much here. But I had a lot of comments in my outfit journal about bad proportions on my two-piece ensembles. When I wore pants with a top, I didn’t achieve “the golden ratio” of one-third to two-thirds and instead was somewhere in between that and a look that pretty much cut me in half.

I was able to mitigate this effect by wearing a small heel (which I like to do anyway) and having low contrast between my top and pants. When both my top and my pants were the same or a similar color, the “cutting in half” effect of a longer top was much less obvious. Wearing heels visually lengthened the line of the bottom half of my body, making it look closer to the two-thirds benchmark.

I also tried wearing tops with a twist-hem (I showed a few examples in this August post), but I didn’t love those as much as I thought I might. I think I either need looser-fitting versions of such tops, or I just need to try the “rubber band trick” with some of my non-twisted tops to shorten them and add visual interest. Unfortunately, when I wore the twist-hem tops that I bought this summer, I thought they were too tight and too long to create the flattering look that I was after.

I’m going to try the twist-hem tops with full-length pants to see if that looks better, but I didn’t like the way they looked with my cropped summer pants. They also didn’t look good with a cardigan or jacket layered over them, so they have limited utility in my closet. Fortunately, they weren’t expensive, but I probably should have just bought one and waited to see if I was happy with it before I purchased additional versions. Buying “multiples” remains one of the shopping behaviors that I need to watch out for.

When I add a third piece to my top and pant outfits, the proportions are a lot better, as most of my toppers are long (I love a good long cardigan or duster). So, I either need to get past some of my body image issues (easier said than done!) and wear shorter tops, or I need to just let go of trying to have “golden ratio” proportions with my hot day ensembles. We’ll see how it goes next summer, but at least I have more awareness of why some of my warm weather looks work better than others. Some of the “action items” that I’ll share in part two of this series should also help me to create more highly-rated outfits in summer 2024.

Dress and Skirt Issues

Other than feeling like many of my dress and skirt outfits look too conservative or dressy, I also found myself not liking some of the pieces that I enjoyed wearing in previous years. I put a few of my dresses into my “holding zone” box, as I either didn’t reach for them at all or took them off before wearing them out of my house. It was also kind of a “Goldilocks” problem, in that the dress was either too loose or too clingy and maybe also too short or too long. I found myself not wanting to settle for dresses that didn’t hit the “sweet spot” in terms of fit and length. We’ll see how I feel when I revisit all my dresses when the warm weather rolls around again.

Another issue I had with dress and skirt outfits was that I no longer liked the toppers that I used to pair with them. The tie-cardigans that I own feel “fussy” and often too short as well. Most of them also have what’s supposed to be three-quarter-length sleeves, but they are more like two-thirds-length sleeves on my long arms, which isn’t ideal.

I could see myself still liking tie-cardigans that are a few inches longer in the sleeves and in the overall length, but I also want to explore wearing alternate types of toppers with my dresses and skirts. Depending upon the dress or skirt in question, some of the toppers that I already own (particularly the longer dusters) might work well. But I could also see myself purchasing one or two new third-pieces to pair with my skirts and dresses next summer once I get a better idea of what might work best.

Conclusion – and Your Thoughts?

So, as you can see, I learned a great deal from reviewing the past four months of outfit journal entries. There are still more lessons that I can recount, but that will have to wait for part two, which I plan to post in about a week. In that installment, I’ll share additional “aha moments” I had that didn’t fit into the “what worked” and “what didn’t work” categories. I’ll also list out the handful of wardrobe tasks I came up with after reading through my comments on my various warm weather outfits. Stay tuned…

Now I invite you to weigh in with any comments or questions you have after reading through this post. Feel free to also share what you’ve learned about your own outfits this year, whether or not you keep an outfit journal. If you enjoy reading these types of posts, you can check out the ones I did on Recovering Shopaholic from 2014 through 2016. Comments are closed on those posts, but you’re welcome to share your thoughts in this essay’s comment section if you’d like.

In the coming weeks, I plan to review my outfit journal entries from last winter and spring, and I’ll do another post or series on what I learn from that experience. Since the cool weather season is just beginning, it’s the prime time for me to improve upon my outfits and overall style for this time of year. I don’t struggle as much with my ensembles when it’s colder out, as there are more opportunities for layering and creating better proportions and more interesting looks that way. But even so, there’s always room for learning and improvement, so I look forward to more lessons learned and sharing them here on the blog.

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13 thoughts on “Lessons from My Summer and Fall Outfit Journal, Part One

  1. Sue says:

    It’s good to see another post at last 🙂.

    The lines here that most resounded with me are, ‘I need to just focus on wearing and loving what I already have until I need to replace a worn-out item or if I happen upon something I love that’s dramatically different from my existing pieces.’

    Debbie, I think they sum up one of the most significant takeaways I’ve had from your posts. I don’t keep notes or take photos of outfits but I try to wear everything and in different combinations, and I always like to decide at the end of each day whether each item is (still) a winner or (maybe) needs to go.

    1. Debbie Roes says:

      I really liked that line, too, Sue, and I need to re-read it often!! I don’t think it’s always necessary to keep notes or take photos of our outfits, but it can be helpful to do it from time to time. It’s great that you make an effort to wear everything you own and create different combinations. It’s easy to get into a rut of wearing the same small number of things over and over again (which is only a “bad” thing if the person feels stagnant or uninspired). I like to “test drive” either “iffy” items or combinations that are out of the ordinary for me during low stakes outings (like when I’m running errands for an hour or two). Just trying things on at home doesn’t always give us all the information we need for the “keep or purge” decision, but wearing a piece or outfit for a period of time usually makes things clearer.

      1. sue says:

        Oooh yes! And a thorough test drive before the return window closes is a must!

  2. sewtypical says:

    Great points, Debbie! I have some of the same issues you have with summer dressing, since we seem to have similar body shapes and are both tall.

    I wear tee shirts a lot, day to day and for exercising. I like to hide my upper arms (self consciously). And the sleeves on women’s tees are always too short for me.

    One thing I’ve gotten better at: if some piece of clothing bugs me in any way, I just put it straight into the donate bin. I want everything in my closet to make me feel good about myself.

    1. Debbie Roes says:

      It can definitely be difficult to find clothes that fit us well when we’re either taller or shorter than average, but there do seem to be a lot more clothes out there for petite women vs. tall women like us. I have seen tee shirts with longer sleeves at some of the stores that cater toward “more mature” women, such as Chico’s, J. Jill, and Talbot’s. You might also want to check out Lands’ End and L.L. Bean, as they might have some shirts that could work for you.

      Good for you for getting rid of clothes that bug you in any way. I’m doing much better with that myself, but I still need to watch out about doing ill-advised alterations to try to “fix” something that is better passed on. Standard and easy alterations can work well, but if I don’t love the item in question, why spend more money on it? It’s just about my guilt for having bought it or not having worn it enough, but I have to remember the sunk-cost theory!

  3. Jenn says:

    I’ve been noting my ideas for habits I want to work on in 2024. I love the idea of keeping a wardrobe journal, and I think I’m going to make it a point to do this next year. I’ve already created a document that included the points you cover in yours. I use the Stylebook App to keep track of my clothing, and I have captured outfits there from time to time. I may do more with that too.

    I don’t know about you, Debbie, but I’m looking forward to Black Friday and Cyber Monday being over. So many temptations! I’m usually very particular about what I keep, but the cycle of buying and returning can consume so much time and energy.

    1. Debbie Roes says:

      From what I know about you, Jenn, I think you would benefit from keeping a wardrobe journal, even if just for part of each season. I’ve been intrigued by Stylebook, but I think it’s only available for iPhones and I have an Android. I think it would be helpful for me to capture more of my favorite outfits so I can remember to wear them again. I often remember the best ones, but sometimes they can slip my mind. I hope you report back on what you get out of keeping a wardrobe journal.

      Yes, I very much look forward to Black Friday and Cyber Monday being over, as there is far too much temptation! What happened to Black Friday and Cyber Monday being ONE DAY each rather than what seems to be WEEKS now?!?! Like you, I’ve gotten far more particular about what I keep, but the buy/return cycle can certainly be exhausting. Unsubscribing from mailing lists and catalogs can be helpful, but there are advertisements everywhere! I struggled so much during my worst years of overshopping, but it’s FAR more difficult to stay on the straight and narrow now 😦

  4. Murphy says:

    Even though I didn’t keep an outfit journal for my warmer weather clothes, after reading your post I’m inspired to go into my closet and identify what my favorite warm weather outfits were. Then I can analyze why, and figure out how to improve my purchase choices for the new season. Great idea!

    1. Debbie Roes says:

      I think if you jot down some notes now while things are pretty fresh in your mind, Murphy, you will be in a good spot for next summer (as long as you review those notes before the season and before doing any shopping for those types of clothes). I still need to jot down my favorite outfits in a more easily accessible place, and I may take photos of them (even just a screenshot of the items together) for easier memory. The more awareness, the better, I say.

  5. RoseAG says:

    I agree with you about twist-tied tops. What if you want to layer it or tuck it in ? You’ve got that twist business there in the way.

    I think it’s OK to say goodbye to things you’ve worn a lot but no longer make you happy. I always liked your tie sweaters.
    I think you mostly got your monies worth out of them, and can send them off if they’re still in wearable shape.

    Now that I’m fully remote I don’t keep an outfit journal because my wardrobe has shrunk. However, the change of seasons is a good time to go through my drawers and closet as I switch out to heavier clothing, and edit things that haven’t worked out. At this point my only hard thought is that I am not buying another peasant/gathered neck blouse. I like the look but rarely wear them.

    1. Debbie Roes says:

      Yes, Rose, there’s the “convenience” of the twist-bottom tops, but they are less versatile because the tied part is fixed and can’t be untied. Maybe they work well for some people, but there are definitely potential issues with them. I still like tie cardigans, but I want them a couple of inches longer now, as I feel that would be more flattering on my changed body.

      I agree that the change of seasons is a good time to evaluate our clothes and how well they are or aren’t working for us. I always do at least some level of closet audit at that time (will write about my most recent one soon). It’s good that you recognized that the peasant/gathered-neck blouses aren’t getting wear with your current work-from-home lifestyle. I’ve had quite a few things over the years that I liked the look of but didn’t wear for one reason or another. Awareness is power and helps us to avoid mistakes, so even if you don’t keep an outfit journal, you’re still having “aha moments.”

  6. The 1/3 to 2/3 golden ratio is so difficult to achieve in a two piece outfit! If you’re not wearing a short top or tucking in your top, the proportion is going to vary from that ideal. This is an area where I’ve had to decide that the top-to-bottom proportion is something I can keep in mind when an outfit fails, but it’s not something I can highly prioritize because I’m just not going to hit it on the mark frequently and I would be setting myself up for failure. For me, this is definitely an area where “good enough” has to be “good enough.”

    I think I find the “off” proportions are more problematic in my outfits the more volume the bottom of the outfit has. With a slimmer leg pants or a pencil skirt, I can more easily get away with something closer to a 1/2 to 1/2 ratio than I can with a wider leg pant or more voluminous skirt.

    I agree that the pants/skirt length also plays into it. Crop pants that are neither shorts/skimmers (just below the knee or higher) or ankle pants (or longer) create the most awkward proportions in my opinion. My most successful two piece crop pants outfits have either shorter tops or low contrast between the top and bottom; it doesn’t have to be a true column of color, but something where the dividing line between top and bottom is less pronounced than, say, a white T + black crops.

    Another thing I’ve let go for summer is focusing too much on the figure flattery aspect of my tops. I have made my peace with woven linen for hot days even though the fabric stands out from my body more than knits and even woven cotton does. With repeated wearing, I am becoming more psychologically comfortable with the looser and sometimes boxier fit of these tops. I think we sometimes don’t give ourselves a chance to adjust to something different, so wearing them on repeat helped me get used to the different look. In my case, the physical comfort of the cooler fabric made this adjustment period completely worth it to me, and with every wear, I learn more about how to make these tops work in creating outfits that are “flattering enough.” Do all these outfits hit an 8+ out of 10 on a figure flattery score? No. But as long as the outfits have an overall high score, I’m fine with that.

    Ironically, perhaps, I find that when I don’t focus too much on whether an outfit “makes *me* look *great*” (is flattering to my body size/shape, coloring, and all that) in all respects, I enjoy my outfits more. I know that this is the opposite advice we usually see, but I think too much focus on it can be as detrimental as too little focus. I think it’s also OK to say “My outfit today has colors/prints I adore and creates a style vibe that feels good to me and has things in it that I love, so it’s a good outfit for today” even if it has 1/2 to 1/2 proportions or a less-than-great fit/silhouette.

    I also find that outfit colors that flatter my coloring are more easy to achieve than outfit shapes that flatter my size/shape (which I think is probably true for most of us!) so that may be a more worthwhile place to focus the “I want this to be flattering/make me look good” energy.

    It’s funny – I can imagine that this may strike some people as one of those “easy for you to say” situations, but it’s definitely not because I’m a willowy young model who looks good in everything. I’m a fat (2X-3X) middle aged woman who has just accepted that my size, shape, and age are what they are. I mean, basically I’ve had to accept it because the alternative is self-hatred, and I don’t know about you guys, but I don’t have enough time left to waste on that.

    1. Debbie Roes says:

      You always leave such insightful comments, Sally. I got a lot out of what you wrote here. I have come to a similar conclusion as you have regarding outfit proportions. I don’t highly prioritize top-to-bottom proportions as much, either, but I have learned some ways of making things work better (the “good enough” that you wrote about). I agree that outfits with more volume on the bottom can be more challenging, although I would like to try wearing some wider pants (but not super wide) and will have to figure out which tops will work good enough with those (even if I don’t achieve the Golden Ratio).

      It’s good that you’ve made peace with woven linen for hot days, as I know it can get pretty hot and humid where you are. It’s true that if we wear things more often, our eyes can adjust to different types of looks than what we previously wore. Physical comfort can be more important than style sometimes, especially on the hottest summer days!

      I loved what you wrote about liking your outfits more when you don’t focus so much on how flattering they might be. The same is true for me, and I agree that it’s easier to achieve flattering colors and patterns than flattering proportions a lot of the time. Thanks for sharing that you’re not a willowy model because there are a lot of bloggers/YouTubers who say similar things about figure flattery who are very young and very thin, and sometimes those who are viewing their content don’t find them relatable.

      Self-acceptance is so important for all of us, and self-hatred is NOT a way to live. I have struggled a lot with my self-image and body image, and I continue to work to make peace with what is rather than what I wish was true (still very much working on the hair piece and my bottom half). I completely agree that we don’t have enough time to waste on hating ourselves and the way we look!

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