My Wardrobe, Myself

I always like to review my wardrobe at the change of seasons, as that’s when I’m best able to evaluate which pieces and outfits worked best for me, as well as what didn’t serve me quite as well. As I’ve mentioned previously, there are really only two seasons where I live in Southern California, which I’ve sometimes referred to as “summer” and “not summer.”

The “not summer” season tends to be much longer, and it usually spans from late October through sometime in June or even early July.  The warm weather arrives later where I live than for most people in the northern hemisphere, but now that it’s finally here, this is a good time for me to review the closet pieces that I’ve worn during the cooler months.

I’m actually going to do two closet reviews. I’ll start today with my cool weather debrief, and then I’ll do a “check-in” on my warm weather wardrobe in my next post. Today’s review will be better informed, as I just finished wearing my cool weather pieces for the past seven to eight months, but I also see the value in an early season review for my summer items. I’ll share more about that in my next essay, but let’s get going with my end-of-season debrief.

Some Closet and “Holding Zone” Information

Since I live in a temperate climate, I keep all my clothes in my closet year-round. I’m lucky in that I have a relatively large closet (I share it with my husband, but my wardrobe occupies two-thirds of the space), but I also worked hard to pare down my clothing such that I no longer need off-season storage. That said, I do still have my holding zone boxes, in which I store items that are either too large or too small for me, as well as things that I’m not sure I want to keep for style-related reasons. Because I can be fickle about what I do and don’t like, I usually wait at least a few months before passing something on, as I’ve been known to come back around to liking pieces often enough to merit that practice.

While I had hoped to get back to just one holding zone box, I still maintain two, as my size has been in flux due to menopause, stress, and health issues. I don’t want to let go of items that I still like until I can be reasonably certain that I won’t need the larger or smaller sizes again. When I finally lost the weight I gained during menopause weight gain about two years ago, I gradually got rid of anything that was more than one size too large, but I held on to liked pieces that were a size up. I’m glad I did that, as I’ve brought a few of those items back into my closet after seeing my weight creep up a bit again over the past year or so.

So, I now have both too-small and too-large items in my holding zone. The former are just slightly too small for me to wear comfortably, but I hope to be able to wear them again soon after adjusting my lifestyle habits.  As I approach the big 6-0 (in 2026, but I feel it edging closer!), I’ve found that I have less margin for error with diet and exercise, which I’m sure is something many of you can relate to!

I Made Some Alterations Mistakes…

One mistake that I made after I lost weight was having too many of my clothes altered to fit my smaller body. While I’m happy with much of the tailoring I had done, I admit that I was overzealous with the process, especially as some of my weight loss was brought on by life stress. I tend to lose my appetite and eat much less when I go through difficult times, but can be prone to viewing any resulting weight loss as more “permanent” than it might end up being.

While I believe that I lost some of the weight due to my post-menopausal hormones leveling off, the stress-induced weight loss has proved to be more difficult to maintain. I’m not sure how much weight I’ve gained back, but I’m also unsure of how much I initially lost, as I never weigh myself. The number is just too triggering for me given my eating disordered history, so I avoid it.

Sadly, some of my now-too-small clothes are due to alterations that never should have been done. We’re not talking about a lot of pieces, but it’s still frustrating for me. It’s one thing if a piece is so big that it looks sloppy, but I was just being a perfectionist about fit to a degree that was unnecessary.

I need to remember my tendency for weight fluctuations when contemplating alterations, particularly when it comes to pants. If gaining a few pounds will render a garment either too tight or uncomfortable, that’s not the best approach to having a workable wardrobe, not to mention being kind to myself.  While I don’t want to undergo big swings in weight, I also don’t want to pressure myself to adhere to a very narrow weight range. So, I’m going to be a lot more careful about doing alterations and buying super-fitted clothing moving forward.

My Favorite Cool Weather Pieces

Weight gain and ill-advised alterations are two of the negatives in this end-of-season review that I needed to mention, but now I’d like to move to something more positive. Let’s look at what my favorite pieces of this past cool weather season were in terms of clothing, shoes, and accessories. I’ll show photos of the items by group and share some thoughts about each grouping.

Favorite Tops

The twelve tops below were my favorites from this past season:

As you can see, I preferred printed pieces over solids, and I continue to love stripes. I also like plaid and space-dye in terms of prints, and most of the prints include black in the mix. When it comes to necklines, crew-neck is my preference, and I often like to wear a necklace with that style of top. I like V-necks, too, as long as they’re not too low-cut. There’s only one 3/4-sleeved top among my favorites, as I prefer the ease of layering that full-length sleeves provide. However, I will often push or roll my sleeves up when I’m not wearing a topper, as I find that is a more flattering look.

Some of the tops above have been in my wardrobe for years, while a few of them are relatively new to me (all the solid tops, as well as the two plaid tops). I’d love to find another one or two tops with a neckline like that of the purple top at the bottom left, as that twist-front is especially flattering on my frame.

Favorite Toppers

I was surprised to see that I had more favorite toppers than tops this past season. The sixteen toppers below include coats, jackets, and a vest, but cardigans remain my most-frequently-worn type of topper.

I’m sure it’s no big surprise to see so many black pieces in this grouping. While some of them might appear quite similar, there are important differences in terms of fabric weight and garment length that are difficult to discern from the photos. Unlike my tops, I have more solid toppers than patterned ones. However, I’d like to add a few more printed cardigans or jackets to my wardrobe for the next cool weather season. I’ve found that they tend to add more visual interest to my outfits, especially when paired with solid tops (so I may need to purchase a few more of those, too, to help balance things out).

Besides my beloved black toppers, I also love my blue, red, and green cardigans. As some of my toppers have been in my closet for multiple years, I may need to pass them on soon because they’re showing signs of wear. I could see purchasing both burgundy and purple toppers next year, in addition to a couple of printed pieces. Most of my toppers are long, as I’ve found that longer lengths look better on my tall frame and short torso. Also, I struggle to find shorter jackets that hit me at the right spot, as I mentioned in my last post. I’d love to buy at least one new shorter jacket, though, just to add some silhouette variety to this area of my wardrobe.

Favorite Pants

This is the area of my cold weather wardrobe with the least variety. While I have lots of different colors and style of pants in my summer collection, I struggle to find pants that are long enough for me in full-length styles. So, I keep my cool weather pants simple and add visual interest with my other garments and my accessories.

The four pairs of pants below were worn most often this past season. Please note that I don’t wear the second and third pairs rolled like they’re shown. I like a “boyfriend” style of jeans because they tend to include ease in the hips and thighs, but I always wear them unrolled and full-length.

I wear the jeans far more often than the black pants, as I struggle with feeling like my black pant outfits skew too dressy. When I wrote about that issue earlier this year, I received some excellent feedback from readers, so I plan to cultivate better casual black pant ensembles when the “not summer” season rolls around again (for some reason, I find this easier to do with my summer black pants).

The jeans on the right have been in my wardrobe for many years. They’re a bit loose in the waist at present, but I’ve been using these inexpensive button pins to cinch the waist in as needed on those and several pairs of jeans that that I’ve been wearing.  Since I struggle with abdominal bloating quite often in the evenings, I can easily adjust the waistband of my jeans using the button pins, which helps me to feel more comfortable.

I actually own two pairs of the third style of jeans, as I liked them so much and was able to get the second pair on sale. I really hope these jeans will be offered in another color (maybe a dark wash or black) in the fall, as they fit me quite well and are comfortable to wear. I don’t mind wearing the same few pairs of jeans over and over. I own other jeans, but I don’t like other silhouettes nearly as much as a relaxed straight-leg fit. Some of my other jeans are too slim-cut, which I feel accentuates my larger hips and thighs. That’s something that is emotionally uncomfortable for me, so I may end up passing those jeans on.

Favorite Shoes

During the cooler months, I almost exclusively wear boots. Since some of my favorite pairs started to look sad this year, I invested in several pairs of new boots. Almost all the boots shown below are new as of this year:

Again, there is a lot of black among my favorite cool weather footwear. The third and fourth pairs shown have been in my closet for five-plus years and are showing their age, but I’ll continue to wear them until they are too shabby to be seen in. I especially love the Munro peep-toe booties, which I wear when it’s cool but not cold out. I’ve had an eBay alert for a replacement pair for at least two years, but no such luck yet…

Again, it probably looks like my black boots are extremely similar, but what’s not obvious is that one pair is suede and other includes a pattern (second pair in top row). After buying the burgundy pair and loving the way they looked and felt, I opted to purchase the black version, too. Those boots quickly became a workhorse, as they’re quite casual and work well with my outfits. I wear the other black boots a lot, too, though, as I wear black footwear more often than not during the cooler months.

My new boots were all relatively inexpensive, as I took advantage of sales at DSW and on Amazon (I bought the faux suede boots there). The only new boots that I could see adding to my wardrobe would be a pair of navy boots and a pair of metallic/pewter boots. I’ve been trying to find a good pair of metallic boots for a few years, but they’re usually either too bright or have too high of a heel for me. I’ll keep looking, though, as I know I would wear that style often.

Favorite Purses

I alternated among the four purses below all season (and I will continue to use these bags in the summer, too, along with two others):

Each of these bags has been with me for over ten years! In fact, the second one used to be brown, but I had it dyed black once I decided that I didn’t like wearing brown items anymore. With the exception of the third one, the purses above are all Brighton (and yes, they’re all black or include black). I still like that brand a lot and would purchase another bag from them, but I’m also open to other handbag designers. I’d like to add another purse or two to my closet in the next year. My priority will be another metallic bag, but I think it would also be fun to buy a brightly-colored purse, perhaps in red, burgundy, or blue.

Favorite Jewelry

Last but certainly not least, let’s look at my favorite jewelry from the recent cool weather season. I actually wear the same favorite pieces all year round, but I tend to include more colorful jewelry pieces in the summer months in addition to what’s shown below.

As you can see, most of my favorite jewelry pieces are silver and black, while others are just plain silver. I never wear gold, rose gold, or bronze jewelry, as I look best in cool-toned pieces. I love gunmetal jewelry, too, but I haven’t seen much of it for sale for years now.

Many of my favorite jewelry pieces were purchased over the years at my favorite jewelry and gift shop in the Lake Tahoe area, where most of my family members live. Most of it is hand-crafted by Native American artisans in the Southwest. I’ve also started buying jewelry from J. Jill over the past few years, as they carry some beautiful and unique items at reasonable prices.

I like to wear long necklaces more than short ones, but one of my favorite necklaces is short with a two-sided pendant that I bought from a consignment store about ten years ago. I also like to wear oblong earrings, as I feel that they’re more flattering with my face shape than rounder styles. I probably have enough silver-and-black pieces now, so if I buy new jewelry items, I will aim for more color. As I mentioned above, I do own some brighter pieces, but not all that many in comparison to my silver-and-black collection.

Cool Weather “Benchwarmers”

Now that I’ve shown you my favorite pieces from the recently-ended cool weather season, I want to share a bit about the flip side of the equation, the “benchwarmers.” While I won’t go into as much detail about these lesser-worn items, I’ll encapsulate some of the characteristics that they have in common.

I don’t have all that many benchwarmers and many of them do get worn sometimes, but I’d much rather wear the favorite pieces that I highlighted above. I’m summarizing these lesser-loved items to help remind myself not to purchase these types of items in the future. I’m also doing so as an example for those of you who might relate to what I’m sharing here.

• Toppers that hit me in a bad spot – I have one jacket and one vest that end in a less-than-flattering area on my body. Since I’m tall, I’ve found that many mid-length garments that fall a few inches below the hips on other women tend to stop right at the lower hip area on me. I really like both of these pieces in theory, but just not on me.
• Toppers that are too snug after recent weight gain – I have four toppers (a coat, a vest, and two cardigans) that fall into this category, and I’m hoping to be able to drop the excess weight and wear them again when the temperatures drop again. I tend to gain weight in the upper-rear-end area, and just a few extra pounds can take an item from flattering to unflattering territory quickly. A lesson here is to allow for more ease in that area to better accommodate weight fluctuations.
• Wide-leg jeans – This silhouette, while currently popular, looks “off” with the other pieces in my wardrobe. While I like the way these pants look on their own, I’ve found them difficult to coordinate without buying multiple new garments. I haven’t gotten rid of them yet, but if I can’t create outfits that I like with them without going shopping, I may opt to do so.
• Black pants – I only really wear the slim-leg black pants shown above, but I own several other pairs. I used to wear full-length black pants all the time, but I now prefer to mostly wear jeans during the “not summer” season. I wear black athletic pants regularly, and I also wear black cropped pants in the summer, but I haven’t been as into wearing black pants in cooler temperatures for some reason.
• Tops and toppers that don’t include black – These aren’t complete benchwarmers, but I don’t wear them nearly as often as my black and black-printed items. However, I’ve started to enjoy wearing navy more often, so some of my rarely-worn pieces might make their way out of my closet more regularly when the cool weather rolls around again.
• Turquoise earrings and bracelet – I love the look of these pieces, but I’m not sure what to wear with them. I feel like they clash with a lot of my clothes, so maybe I should only wear them with either all-black or black-and-white outfits. I need to work on wearing more of my jewelry, especially those pieces that I really like.
• Arche Enexor sandals – I own these lattice-style sandals in three colors, but I don’t like to wear them anymore because I feel they skew too dressy and perhaps too old-fashioned, too. I’m planning to sell the red pair (it’s too tomato-red anyway) and maybe the metallic pair, too. I’ll likely hold on to the black pair for the rare dressy occasion, but I certainly don’t need three pairs of this style of shoe!
• Scarves – I own a fairly large scarf collection, but I almost never wear them anymore. Perhaps it’s because they aren’t easily visible (I have them stored in a box because there’s no good place for them in my closet), or maybe I’m just more into necklaces these days. I will hold on to most of them, as it’s possible I may come around to wearing them again, but they’ve been benchwarmers the past few years.

I’m not getting rid of all of these benchwarmers just yet, but I have passed along some other cool weather pieces this year. I was going to cover those in today’s summary, but it’s already getting very long at this point. I’ll do a closet purge post soon to review what I’ve gotten rid of and why so far in 2024.

Biggest Cool Weather Wardrobe Challenges

I’ll close out this post by summarizing my biggest challenges when it comes to my cool weather wardrobe. Some of these challenges apply to my summer wardrobe, too, while others are confined just to “not summer.” I’m not sure how to address many of them, but identifying our challenges is always the first step toward change, so here goes…

• Weight fluctuations – I covered this quite a bit earlier in this post, but I’m including it in this section, too, as it’s one of my biggest challenges with my wardrobe at large. Unfortunately, I tailored some of my clothes too much and now they’re tight, so hopefully I’ve learned my lesson not to aim for a perfect fit that requires staying within a very narrow weight range.
• Poor body image – Yes, I’ve gained some weight, but my reaction to is it out of proportion to how much I’ve gained. It’s not even a full size, yet I’m having a really hard time with it. Clothes can make body image challenges either easier or more difficult, though, so I’m only going to wear things that I feel good in, even if other pieces technically still fit me.
• Long pants and jeans – It’s so hard for me to find bottoms that are both long enough and comfortable enough to wear all day long. I have many cropped pants in a variety of colors and some patterns, but my long pants wardrobe is very limited. I don’t really mind wearing the same few pairs of pants all the time, but it would be nice to have some other options.
• Proportions – I like to cover my rear end because I’m self-conscious of it, but that often “cuts me in half” proportionally. This effect is less pronounced when I wear a long topper, but it can be more noticeable when I remove my cardigan or jacket. Wearing heels helps, too, but I either need to be okay with less-than-perfect proportions or find a way to be less self-conscious when I cultivate better proportions. Wearing looser pants helps, as I feel those are more flattering to my back side, so I plan to focus on those silhouettes most of the time.
• I don’t wear enough of my jewelry and I’m not wearing my scarves – I covered both issues above, but this is something I’d like to work on. Perhaps I’ll challenge myself to wear more of these items by designating a few pieces to coordinate into outfits each month. I love the pieces that I do wear, but I also really like many of my unworn or rarely-worn pieces as well.
• Not enough “special” tops – This is more of a problem in warm weather, as I can’t always layer, but it can be an issue in the cooler months, too. I often feel like I need a “third piece” or a lot of accessories for my outfit to look sufficiently interesting and pulled together. Tops have been especially challenging for me to buy the past few years, probably because so many of the ones on offer have been cropped or just too short for me. I’m hoping as trends cycle through, longer lengths and less boxy silhouettes will become more readily available once again.

Conclusion – and Your Thoughts?

Well, that seems like a lot of challenges, doesn’t it? But I also feel like I had a fairly successful cool weather season in terms of my wardrobe. I rated the majority of my outfits as eights or higher and I felt good in what I was wearing. I also was happy with many of my pieces, and I made some great purchases that added a lot to my wardrobe. I rounded out my boot collection and bought some toppers, jeans, and jewelry items that quickly became “workhorses.”

Overall, I find it easier to get dressed in the cooler weather because I’m able to layer and take advantage of third pieces. Yes, my bottom options are more limited, but I make up for that by wearing more interesting tops and toppers, as well as lots of fun jewelry pieces. We’re now moving into the more challenging summer season when it’s often too hot for a topper and I feel more self-conscious wearing less clothing. I’m in the process of reviewing what I own in terms of warm weather clothing, and I will do what I guess I’ll term a “preview” post on that subject soon.

I hope you found this cool weather wardrobe debrief interesting and that perhaps it helped you to consider how well your own wardrobe worked for you when the temperatures dipped lower. If you have any insights that you’d like to share on that subject, I welcome your input. Likewise, if you have any questions or suggestions for me, please leave a comment.

For those of you in the United States, I wish you a Happy Independence Day. If you’re traveling or will have a long weekend next week, I hope it will be enjoyable for you. My husband and I will be celebrating our twenty-third wedding anniversary (and the twenty-fifth anniversary of the day we met – which yes, was July 4^th!).

To all of you, thank you for reading my very long diatribe today! I appreciate your readership very much.