The holiday season has officially begun, for better or for worse. I hope all my readers in the United States enjoyed some quality time (and delicious food) with family and friends over the long Thanksgiving holiday weekend. Instead of perusing Cyber Monday offerings this afternoon and being tempted by the many “deals” on offer, I’m opting instead to write this blog post.
It’s far too easy to go overboard and buy things we don’t need this time of year, as the temptation of seemingly continuous sales lurks around every corner, whether it be in person or on our computers and phones. I’m still far from perfect in terms of my shopping, but I hope that by turning more of my focus inward to what I have and what I’ve learned, I can get through the often frenzied “shopping season” without incurring too much financial damage.
Today’s essay is part two in my series on lessons from my summer and fall outfit journal. In my last post, I wrote about what did and didn’t work in terms of my warm weather ensembles. Today, I’ll share some additional lessons from my outfit journal entries that didn’t fall under those categories. I’ll also reveal a series of action items that I derived from my commentary on the looks I wore from June through November. Some of those tasks will apply to the current cool weather season, while others will help prepare me to dress truer to my personal style aesthetic next summer, as well as maximize my physical and emotional comfort levels in what I wear.
Some of my wardrobe-related tasks will likely be the topics of future blog posts, especially those that relate to my 2023 wardrobe and style “bucket list” (see part two HERE), which is certain to carry over into 2024. It’s hard to believe there’s just one month left in the year! Time definitely moves faster as we get older (so I’ll have to do more to increase the novelty in my life). Even more reason why we shouldn’t wear outfits that are uncomfortable, fussy, or boring!
Other Things I Learned from My Outfit Journal
Not all the realizations that I noted from my outfit journal fit into the “what worked” or “what didn’t work” sections that I covered in my last post, so I’m listing them here, along with further commentary on each of them.
When I push myself to wear “benchwarmers,” I often don’t like my outfits.
While it can be good to evaluate unworn or lesser-worn pieces to see if we can make them work, sometimes we just need to accept that we made a mistake in purchasing certain items. Trying too hard to make a piece work has been one of my biggest wardrobe mistakes, especially when it has involved ill-advised alterations.
It’s difficult to get past the feeling of regret at having spent money on something that didn’t work for me. However, I’ve learned that taking a ho-hum piece to my tailor in the hope that a nip and tuck might make me love it is all too often a recipe for more wasted money. Selling things online has helped me with my guilt in the past, but it’s also quite time-consuming, so that aspect needs to be considered as well. Sometimes just donating an unloved item is the best path to take, and once it’s out of my home, the guilt often leaves with it.
I need to be careful about buying “multiples.”
As one example, I lamented in a summer outfit journal entry that a pair of Brooklyn ankle pants was baggy in the rear end, which led me to only want to wear them with longer tops and toppers. That’s limiting, but what’s worse is that style of pant dominates my summer wardrobe! I own Brooklyn ankle pants in black, navy, navy print, olive, lavender, and purple, all of which are a little baggy in the seat area. So, I either need to alter each of those pants, accept a bit of bagginess (the pants actually have that same effect on some of the models), or be limited to wearing them solely with longer companion pieces.
I don’t need many summer shoes (or shoes in general, really).
I happily wear the same few pairs of sandals over and over again all summer long. Yes, I own other summer shoes besides the ones pictured below, but I rarely wear them and don’t really need them. I would be totally fine wearing just the five pictured pairs of shoes all summer long for my out-and-about activities (I wear my walking shoes when I venture out for walks or workouts). Now that I think about it, the same is true for my cool weather outfits, but I plan to address that topic in a future post.
Likewise, I don’t need a lot of clothes.
Just a “smallish” capsule (like I shared in this October post) is enough to cover my needs and offer a decent amount of variety. This realization is what led me to do a closet audit last month. I purged a lot of pieces that I didn’t enjoy wearing, and I relegated others that I was unsure about (or that didn’t fit me well) to my holding zone box. I will revisit the latter group next spring. I may desire more than the 33 seasonal items outlined by Project 333, but I don’t need or even want the much larger wardrobe that I’ve lived with for years.
I’m very happy with my jewelry, but I have too much of it!
Are you sensing a theme here? I own too much in many wardrobe categories, but the jewelry situation is somewhat different because I truly love the bulk of my pieces. However, I feel overwhelmed by it all, even though my collection is much smaller than it was back in the early days of Recovering Shopaholic. Probably the best approach is to rotate the pieces in an out (storing others elsewhere) to ensure that I wear everything. And perhaps as I wear certain items, I’ll decide that I don’t love them as much as I thought and can pass them on.
I’m happy wearing outfits that aren’t necessarily “current.”
A lot of my outfits aren’t necessarily “current” in terms of styles and silhouettes, but I feel happy wearing them. While I don’t want to look like I should be nominated for “What Not to Wear” anytime soon (even though the show has been off the air for years), I’m fine sticking with classic styles and my favorite outfit formulas. When I try too hard to dress the way that I think I’m supposed to, I often end up disliking my ensembles and feeling self-conscious in them.
Most people don’t know the specific formula that the “fashion gods” are dictating in any given season, and even those who do often don’t care if they or others are adhering to it (I know I don’t care if other people are wearing what’s on the cutting edge of fashion). So why not wear what makes us happy rather than trying to please other people who might not notice or care anyway?
One nice thing about getting older is that most people are less afraid to just be themselves and dress how they like. When I’m at the mall, I often see a group of women in their teens or twenties who are dressed almost identically. I rarely see such a thing with middle-aged women, who typically don’t chase trends quite as much.
Action Items from My Summer/Fall Outfit Journal Entries
I jotted down quite a few “to-do” list items while I was reviewing the recent entries in my outfit journal. I’m glad I took the time to create this list so I can gradually work through the tasks to help prepare myself for when the next warm weather season rolls around. Some of the tasks below also apply to the current cooler season, so I’m listing those first.
1. Narrow down my black cardigans to my favorites.
As a lover of both black and cardigans, it’s not too surprising that I’ve amassed a decent-sized collection of these pieces. But some of them have been in my closet for a long time and are past their prime, while others I wouldn’t reach for over my tried-and-true favorites.
It would be nice to have just a few black cardigans in my closet that are distinct from each other and help to create particular types of looks. The rest could either be passed on or stored for when my current favorites wear out.
2. Pare down my scarf collection.
I want to cull down to just the ones I’d be excited to wear and that work well with my personal coloring and the colors in my closet.
3. Designate a few scarves to wear each month.
I need to set these scarves aside in a place where I will easily see them and think to reach for them.
4. Buy a mid-length silver necklace or pendant.
This will be to wear with certain tops in my closet, as I found myself wishing for such an item when my current necklaces didn’t work with those tops.
5. Create a list of at least ten “go-to” summer outfits that look good without a topper.
Ideally, these outfits would be rated at least an “8” on a scale of 1-10 and would also be appropriate to wear for my lifestyle and personal aesthetic. Taking photos of these outfits, either on me or in a “flat lay,” would better facilitate my remembering to wear them.
6. Make a list of tops that work well with my cropped pants without a topper.
Of course, this will depend upon the pants, but I found it difficult to get dressed on the hotter days because I knew that I either didn’t need a topper or would likely need to remove it at some point during the day.
I would ultimately like to list 3-5 tops that I can wear with each pair of summer pants that I own. My cropped jeans seem to be the most versatile because the fabric is more substantial and holds its shape, so perhaps the list of tops I can wear with those pants will be longer. But I think if I can mix and match at least three tops with each pair of pants, I’ll have the versatility that I want with my wardrobe.
7. Single out pants that look good in the back without a longer top or topper.
This task goes hand-in-hand with the last two. I don’t think this list will be very long, but it would be nice to know which pants/jeans fit this description. Even if it’s only two or three pairs, that would probably be enough for me, but I can also take note of the characteristics of these pants so I can endeavor to expand the list next year.
8. Figure out at least three tops to wear with my black Farallon Weekender pants.
These pants are comfortable, but because they’re looser-fitting than my other pants (they’re more of a “barrel” style), I’ve found that they don’t work with many of my tops. I think these pants call for a shorter and more fitted top, but I’ll have to experiment a bit to see.
9. Stretch the waistband of one pair of cropped jeans that was taken in a bit too much.
These jeans have a higher rise than what I usually like to wear, so the tighter waistband is uncomfortable when I sit down. I think that I can stretch it out an inch or so when the pants are wet, though, which will make a big difference to my comfort when wearing them. I also plan to only purchase mid-rise jeans moving forward, as I have a shorter torso and I find higher-rise styles uncomfortable.
10. Purchase two or three longer tie-cardigans to pair with dresses and skirts.
I still like this style of topper for its ease and figure flattery (to highlight my smaller waist), but the ones I own are too short for my current preferences. They hit me in a spot that I feel is unflattering in the back and accentuates my larger behind. I’d rather bisect that part of my body, which was one of the things I learned from watching “What Not to Wear” (this article mentions the bisect guideline under the “hips” section).
This issue with my tie-cardigans played a big part in why I didn’t wear dresses and skirts all that often this past summer, as I almost always need some sort of topper, at least for when I’m indoors with air-conditioning. Most of my pants toppers don’t pair well with my skirts and dresses, but I’m going to play around in my closet some more to see if I have other good options on hand already.
11. Evaluate my short-sleeved and sleeveless tops for what works best with my pants.
I have my tops divided into at-home and out-and-about sections (with further delineations in each), but perhaps some of my more pristine at-home tops might cross over well to wear out and about, too. This might be especially true for some of the neutral tees that could be dressed up through using accessories.
I need to think outside of the box a bit more when it comes to tops, as I’ve been challenged in recent years with finding good options. I also might have one of my twist-bottom tops shortened to see if the proportions work better with my pants. I still like the style, but the longer length of these tops just looked “off” to me when I tried to wear them. I won’t rush to tailor all these tops, but I think it could be worth experimenting to see if they could possibly be salvaged. I will think carefully about whether or not to do this, though, as I wrote earlier in this post about the times when I “threw good money after bad.”
12. Figure out how to best manage my hair on hot and humid days.
This is part of my wardrobe and style bucket list, but I haven’t found a good way to address it yet. Far too many otherwise great summer outfits felt ruined by bad hair days, especially on humid evenings. My hair puffs and frizzes whenever the humidity levels rise, and I unfortunately don’t love the way I look with my hair up with my aging face. I might want to try wearing hats with ponytails and braids during the day, and I can use my baseball cap and braid trick with my more casual looks during the day or evening. Some hats won’t work well at night, though, so I need to figure something else out for those times. I’d like to at least have an option or two available to me so that I don’t feel unattractive sporting a nice outfit with bad hair.
I need to spend some time on YouTube, Instagram, and hairstyle blogs so I can identify a few hair options to try. I also need to be less rigid in terms of what I think looks good on me, especially when it comes to updos. I don’t know that I’ll opt to “embrace” my natural hair texture (which I really don’t like), but I want to be able to relatively quickly shift to an alternate hairstyle in the event of high humidity and puffy hair. That will at least help me to feel better in the moment, which works for me when I put on a baseball cap and pull a braid through the back during my frequent evening walks by the water.
Conclusion
I know there’s a bit of overlap between my action items above and some of those on my 2023 wardrobe and style “bucket list” (part one / part two), at least in terms of my scarves, jewelry, and hair. That list will be carried forward into 2024, as I haven’t been able to complete every task that I outlined (but I did make quite a bit of progress!).
I might create a 2024 bucket list that includes my remaining 2023 tasks, as well as the ones I shared today (and anything else I might think of). Some of today’s tasks are more specific and less time-consuming, but they’re all activities that are worth doing and will likely help me to improve my style – and my wardrobe satisfaction – come summer 2024.
If you have any thoughts about what I’ve shared here today, please feel free to comment. If you’d like to share some of your own wardrobe-related goals and action items for the coming months, I’d love to read about those, too.
I wish you the best during the ongoing holiday season. I hope your enjoyment levels will be high and your stress levels low! Take care, and I’ll be back soon with another post. Some upcoming topics include a debrief of my latest closet audit, a look at my best and worst purchases of 2023, and lessons from reviewing my outfit journal entries from last winter and spring.
My Wardrobe, Myself 
This is not meant to be a snarky comment, but I would maybe try to branch out a bit in your shoe collection. I know they’re comfortable, but they are all quite matronly looking shoes. There’s many more fashionable options out there that are very stylish at the same time.
We’ll have to agree to disagree that my shoes are “matronly.” I like them and am happy wearing them, so I’m okay with others thinking they’re matronly. Style is very individual and at age 57, I’m totally okay with not being on the cutting edge of style. That said, I’m open to branching out with both shoes and clothes, but the in-person shoe selection in the stores where I live is not what it used to be. Since my feet are fussy, it’s challenging to buy shoes online, but I have successfully done so on occasion.
I think your shoes are gorgeous, Debbie, and so does my 20-something daughter who has a very with-it style (🤔 although, come to think of it, I’m pretty sure ‘with it’ is not the right expression these days ☺️). Shine and comfort are in. I’m on the lookout now for those black-studded sandals.
Thank you so much, Sue. I’m glad my shoes get a thumbs up from both you and your daughter. Style is such an individual thing and we’re all entitled to our opinions. The word “matronly” is a bit harsh, but different strokes… I hope you can find the sandals. I think the style is still sold (Munro Pisces), but I’m not sure if the ones with the studs are still out there new (but there’s always the resale sites – I’ve had a lot of luck finding shoes that way).
Debbie, I have THREE pair of BIRKENSTOCKS (pewter, black and tan) and FIVE pair of OLUKAI (black booties, navy, tan and black tennis shoes, and flip flops. And these are the “only” shoes I wear. Matronly? Lol. I do have a couple of pair of “so-called fashionable shoes” but I hardly ever wear them! I’d rather have comfortable happy feet. Perfect for walking miles and miles, which I do!
I’m sure your shoes look great, Terra. Birkenstocks were “all the rage” not that long ago, so why would they all of a sudden be considered matronly? When we get older, we often get fussy feet and can’t walk so well in a lot of what’s considered to be more fashionable shoes. Having comfortable, happy feet is most important. I like to do a lot of walking, too. For my longest walks, I wear actual walking shoes, but I can walk pretty far with the shoes shown in this post, and I’m grateful for that. I like the way they look, too. I completely understand that not everyone will agree – and that’s okay.
Such a “patronly” remark!
So many points where I was nodding my head. Buying multiples, too many black cardigans and finding that certain pants only work with certain style tops, not dressing on trend and not caring about that one bit, etc.
As for me in 2023, in early October, I took everything out of my closet (everything) and picked a base color (black and dark charcoal) and two accent colors (purple and red) and gathered about 40 articles of clothing that I returned to my closet, including shoes. I packed up EVERYTHING else remaining in large plastic storage totes. I am actually doing the capsule wardrobe thing for the first time! All the rest is out of sight, out of mind and wow, what a difference in ease as well as creativity with outfits. It has been two months and my goal was to try it for three and then switch to different colors. I’m not sure if I’ll be ready to switch in just another month though, I may stick with this all through winter, switch it up for spring. It was a bit of (fun) work to get going and to decide what to keep and what to store, but I am so glad I tried this finally. I am learning a lot about what I actually need and how simplicity and ease bring me joy and how restriction inspires creativity.
Thanks so much for sharing your experience, Amber. I love that you’re loving dressing with a capsule wardrobe and are considering doing so beyond the original timeframe you set out to do. How you’re feeling now reminds me of my experience during a trip I took in the summer (which I wrote about a few posts ago). After I returned home, I mostly wore the clothing and outfits from my trip, which felt freeing. However, I still had the rest of my clothes in the closet, so maybe I should try what you’re doing. I may opt to do in a month or so, but I only recently started wearing my cool weather items and I’d like to get a better sense of what my favorites are now (I tend to shift my opinions after months away from wearing a section of my wardrobe). When I did Project 333 in the past, I learned a lot from the experience, but I haven’t done a capsule challenge in a while. Reading your experience is inspiring me to try it again!
Points in this post on figuring out what goes with what resonate most with me at the moment. Particularly like #10 on tie-cardigans and particularly on pairing them with dresses.
Over the past years, I’ve been finding second hand (so inexpensive) tie-wraps and cardigans in natural materials to wear as third pieces with dresses that help me feel physically comfortable and put together. Often, I find a particular colour or style works best with a particular dress so I’ve been partnering the best matches on the same hanger.
It’s not that I won’t break up a set but I find it so much easier to grab an outfit and go if I hang some clothes like this. Skirts and pants seem easier for me to mix and match so I don’t feel the need to hang items together on a hanger so much but it sure helps me with dresses, particularly in summer when it helps to have a very lightweight third piece ready to go.
That’s great that you’ve had such a great experience with secondhand purchases, Sue. I really wish could shop that way, but I’ve developed such a sensitivity to fragrances that it’s gotten difficult for me. It’s nice to have the selection of previous styles that may no longer be “in” but still look great. I like the idea of hanging some outfits together, as that can make it a lot easier to get dressed. We all have times when we have to be out the door very quickly, so it’s helpful to just be about to grab and go.
You are making great gains! From experience I know it takes a whole lot of thought and much pondering to get to where you are now. Your process reminds me of myself and where I was a few years ago. Although I had downsized my wardrobe to a moderate level, I still had too much for me to take care of, enjoy, and wear. These days while I have become minimal in most areas, I’ve decided that I’m perfect happy with a simple “moderately” minimal wardrobe. Probably much smaller than most people want, and yet plenty large enough for me, with enough variety and ease. Finding my balance was hard and keeping it where I want it to be is harder! Age is helping me out greatly. In my seventies now I’m a tiny bit more trendy now than I was in my 50s and 60s and yet I still lean toward classic pieces that I will be able to wear for years if I want. And I’m much faster about letting go of anything that I’m not comfortable wearing, or that was just a mistake to buy in the first place. The way I see it is that I’m in the youth of my old age, and I want to enjoy what I wear! I struggled a lot with my hair and my clothes when I was younger, and I feel like I just don’t have that kind of time anymore. 🙂
I always seem to be a few years behind you, Terra, in terms of my wardrobe and style evolution, but I like reading your words of wisdom and seeing what might be down the road for me. I’m more minimal in other areas of my life, too, but I’m gradually becoming more minimal with my wardrobe, too. You’re right that it can be tough to find our balance (and yes, keeping it is even harder). That’s great that you’re a bit more trendy now after embracing mostly classics for years. The important thing is that you’re happy with what you’re wearing, as you said. I don’t want to struggle with what I wear (or with my hair) anymore, so I’m better about letting things go, especially if they’re uncomfortable or make me feel unattractive. I still have a ways to go with my wardrobe, but it’s nice to feel that I’ve made progress.
Debbie, I can relate to many of your points. I don’t have a lot of benchwarmers at this point but there’s definitely a cache of them and you are so right that when I force myself to wear one of them I frequently don’t feel comfortable in my outfit. Also, I need some duplicates (like black or navy pants) but I need to stop feeling the need to stockpile things. After all, I live in a city where there are shopping options if something basic wears out! And maybe I might want to branch out when I’m replacing instead of getting a duplicate!
I’m definitely trying to figure out what goes with what for the winter season, and what work/everyday clothes balance I need. I’m going to try to come up with at least 10 outfits for each season like you suggested so that I see where I have gaps or am oversupplied. I might be surprised !
That’s great that your number of benchwarmers is minimal, Murphy. It’s hard to have NONE, but minimal is good. We can’t always know that something won’t work, so why beat ourselves up over it? Duplicates can be useful, especially in terms of frequently worn items, but I tend to go overboard. Like you, I live in an area where there are many shopping options. Good luck with coming up with those 10 or more great winter outfits. I used to do outfit creation sessions in which I would photograph 50-100 ensembles, but I no longer think I need that level of variety (and there were always favorites among the group anyway). I hope you will have few areas of overlap and few gaps in your wardrobe, but taking the time to figure it out will help you shop more wisely.
I respect and am inspired by people like you, Debbie, who know and wear what works for them, especially when their intentional choices do not reflect current trends. It makes me feel free to do the same.
Thank you so much for your kind words and support, Jenn! I’m sorry I’m so late in responding to you, but I didn’t get a notification of your comment… Trying to keep up with trends is exhausting, and I often ended up wearing things that I didn’t really like back when I was trying to stay “current.” It’s difficult to even find out what we like and what works for us, and then we’re supposed to change it all every year or so. If that’s what someone wants to do, that’s of course totally fine, but I struggled with it so much. I do try to “evolve” my style over time, but I’m no longer going to wear something just because the “fashion gods” say so.