My Wardrobe, Myself

As I’ve mentioned several times on the blog, I turned fifty-five last August. Shortly after my birthday, I decided to commemorate the occasion with a fun and lighthearted post about my top fifty-five summer closet pieces. I shared photos of all of my chosen items, as well as information about why I selected them for my hypothetical warm weather collection. I followed up that post with a second one in which I analyzed patterns among my capsule pieces and highlighted closet gaps that I discovered through the exercise. I closed out the series with a short list of warm weather shopping priorities to address before summer 2022 (which will be here before we know it!).

I plan to revisit some of the topics from the aforementioned posts in a few months, but I thought it would be interesting to select a cool weather “top fifty-five” collection now since there are still a few more months remaining of lower temperatures where I live (and for many of us). I actually designated items for a “not summer” capsule back in August and intended to share them sometime last fall, but I got sidetracked with other topics. When I revisited those choices a few days ago, I opted to make quite a few swaps. I will explain those changes in part two of this series, which will also address closet gaps and cool weather wardrobe issues identified through doing this exercise.

As with my summer “top fifty-five” essay, I’ll show you the items in my capsule by category and also share a bit of information as to why I made those particular selections. Although I own more cool weather items than what is depicted here (but not nearly as many as I used to have!), the pieces shown represent my favorites, so the capsule should ostensibly work well for me. While my cool weather wardrobe is serving me well for the most part, there’s still room for improvement, which is a big part of what this blog is all about!

When we better understand our wardrobe, our personal style, and our lifestyle and comfort preferences (both physical and emotional), we’re better able to dress in a way that suits our individual needs. The “navel-gazing” and numbers-crunching that I do here is geared toward increasing my own personal awareness, as well as helping you to consider important aspects of your wardrobe and personal style. It’s always my hope that sharing my wardrobe journey will help others to learn and grow – and maybe avoid a few of the pitfalls I’ve experienced along the way. With all that said, let’s check out the capsule!

My Fifty-Five Items

Below are the items – clothing, shoes, and purses – that I’ve selected for my “cool weather fifty-five” collection:

The above capsule is comprised of the following pieces, broken down by wardrobe categories:

• 3 pairs of pants (all black)
• 4 pairs of jeans (2 medium wash, 2 dark wash)
• 5 short-sleeved tops
• 15 long-sleeved tops
• 14 cardigans (all either mid-length or long)
• 1 blazer
• 3 vests
• 6 pairs of shoes
• 2 purses

Seven Pairs of Pants/Jeans

During the cooler months, I mostly wear black pants and jeans as my bottom pieces. While I’ve long struggled to find pants and jeans that are both comfortable and flattering, I’ve finally been able to locate garments in this category that work for me. All of the above pant and jean options have long inseams, which I need for my tall height and long legs. With the exception of the jeans on the bottom right, all of these pants were purchased from 2020 through early this year. I wear the “weekender jeans” (bottom left) unrolled and full-length, even though they’re shown rolled in a boyfriend style.

The Starfish jeans from Lands’ End were my most recent finds that I purchased in both medium and dark indigo shades. They’re offered in regular, petite, and tall lengths, and are extremely comfortable to wear. If you decide to order these pants to try, you might want to size up, as even though a small tall should have worked for me based on the size chart, I found the medium tall to be a better fit. They’re not a super fashionable jean, but they’re a nice basic and can be worn comfortably all day long without the pinching and binding that I experience with most other jeans. The same can be said for the two pairs of Wearever knit pants from J. Jill (only the slim-leg version is available at present), which are as cozy as pajamas but look polished.

I’d like to have more variety in terms of the bottoms that I wear, but it’s not easy for me to find pants that fit me well that are also long enough and comfortable for all-day wear. Consequently, virtually all of the visual interest in my cool weather outfits is currently confined to my tops, toppers, shoes, and accessories. Since I tend to carry any extra weight in my lower half, it’s probably better to draw the eye more to my upper half anyway. The pants and jeans shown above pair well with the shoes and other pieces in my collection, so I’m happy with that.

Twenty-Two Tops

I included twenty-two tops within my cool weather “top fifty-five” capsule. Because there are some unseasonably warm days throughout the year where I live, I opted to include five short-sleeved tops in addition to the seventeen long-sleeved tops that I selected.

As you can see, there are a lot of black and black-printed tops in the mix, but I also chose a small number of bright tops to liven things up. You’ll see more color when we get to my toppers, but I’m usually content to wear mostly neutral pieces with maybe one or two pops of color in an outfit (which are sometimes done through accessories). I’ve branched out a bit with some new colors recently, including the olive color-block top and two navy-printed tops. One thing that works well for me is when tops feature both black and another color, as they coordinate nicely with my black pants, toppers, and shoes.

I rarely wear fully monochromatic ensembles, but that’s something I want to experiment with more, as it can be a sophisticated look and isn’t boring when different textures are incorporated. Because black is my key neutral, I included three solid black tops in my capsule, as well as another top that’s mostly black with a bit of “heathering” to add visual interest. It may seem like overkill, but I wear a lot of black tops and I like to have the variety of different neckline and sleeve lengths.

As I looked back at my summer “top fifty-five” capsule, I noticed that I had even more black tops there, but it helped that I also had two pairs of black printed pants and one colored pair of pants in the collection to coordinate with them. I could possibly wear the full-length black and white printed pants from that capsule in cooler weather, too, especially since I had them narrowed and they no longer scream “summer” with the palazzo silhouette. I may give that pairing a try, and I also plan to keep an eye out for one to two pairs of printed or colored pants for cooler weather.

Eighteen Toppers

The majority of the toppers in my “not summer” hypothetical collection are cardigans, but this part of my capsule is where the most color variation exists. I also included one Ponte-knit blazer and three vests among my topper selections. I didn’t include outdoor-only outerwear such as coats and puffer jackets in this “top fifty-five” collection, but I do have a handful of such pieces that I wear when necessary.

My vests are not as versatile as I thought they would be, as I can only really wear them on warmer days because only one layer of fabric (my top) is covering my arms. I love the way they look, but the longer vests (the two on the right) especially don’t pair well with a coat due to their length. I haven’t been wearing coats all that much this season anyway, instead favoring the mid-length and duster-length cardigans pictured above. On warmer days, I enjoy wearing the vests, as they represent a fun and different silhouette, and I feel that the longer vests look dramatic, which is one of my “style guideposts.”

The black knit blazer is a recent acquisition from Athleta, and I like it so much that I may also purchase it in the other color in which it’s offered (but I’m not sure that color will suit me). I appreciate that it’s a more relaxed blazer style that doesn’t read “corporate,” plus it’s stretchy and very comfortable. One of my style goals is to incorporate new silhouettes, as I tend to wear too much of a “uniform” much of the time. While there’s nothing wrong with dressing in a uniform per se, it can start to feel too “same-y” after a while, even if the colors, patterns, and textures are varied. I’ll always be a big fan of cardigans, but adding some more jackets to my topper collection will help me to broaden my style horizons.

Six Pairs of Shoes

I’m fortunate in that I’m able to wear somewhat open-toed shoes (like peep-toes) most of the year in my temperate climate, but there are definitely some days when it’s just too cold for such footwear. Therefore, my shoe selections are divided between closed-toe and peep-toe options.

The newest addition to my footwear collection are the silver snakeskin booties, which I bought on Poshmark recently. I’m still figuring out how to best wear them, as they’re a bit of a new look for me, but I love that they add color, pattern, texture, and shine to my wardrobe. I wear black shoes more often than not, but I like having the metallic and burgundy options available for when I want something different. I’m not sure about wearing the metallic or burgundy shoes with my black pants, though. I pretty much only wear the non-black footwear with my jeans.

I know that metallic shoes “bookend” my gray(ish) hair, but I feel more comfortable wearing those shoes when I’m showing some of my legs in either cropped pants or dresses/skirts. Perhaps my eye just needs to adjust to a different color shoe compared with my pants. I kind of like the idea of a printed pair of shoes that incorporates black with another color (maybe metallic or white?), but I have yet to find anything that fits that description and suits my fancy.

I used to have a large shoe collection (55 pairs when I started Recovering Shopaholic!), but I now feel that I could probably get by with just ten to fifteen pairs. I did a series of posts last year about applying “the rule of ten” to my footwear selections (starting with this essay). I plan to do an update on my shoes soon, as well as some more posts on the rule of ten, but for now I’ll just say that there’s still a fair amount of “dead weight” in my closet when it comes to my shoes.

I tend to wear the same handful of shoe options over and over again, while others simply gather dust. The same thing can be said for some of my clothing categories, but I’m often more hesitant to let go of shoes because of fit issues and expense. But if I could easily get by with just six pairs of shoes in both my summer and “not summer” capsules, that tells me that I don’t need as many footwear options as I previously thought.

Two Purses

I selected the same two purses for the cool weather season as in my summer capsule:

Both of these purses have been in my closet for almost ten years and are still in great condition, despite being carried for hundreds and hundreds of days each. That’s a testament to the high quality of Brighton bags. These two purses work with pretty much any outfit I wear and they also hold a lot of stuff, which is something I look for in a bag. I like that they both have interesting detailing with either silver studs (the black bag) or patterned embroidery (the metallic bag). The fact that the metallic bag also features black is a big win for me in terms of its versatility in pairing with virtually everything I own.

I’ve gradually pared down my handbag collection over the past few years, such that I now only have a handful of options in this category. I own a few other purses that I use on occasion, but I don’t like those bags as much as the two shown above. My main issues with the other purses relate to either lack of structure (too “floppy”) or size (too small), but I’ve kept them because I like their overall style and they were either gifts or pricier purchases.

I’d be interested in having more variety in my purse collection, yet I haven’t purchased a new one for a long time, other than the failed Cirque du Soleil resale buy that I wrote about in my worst purchases of 2021 post. My main reason for not buying a new purse is that the ones I like tend to be relatively expensive and I often get ahead of myself in terms of my clothing budget. I need to “slow my roll” with the clothes (a familiar refrain…) so that I can do a small refresh in the handbag category of my wardrobe.

I want to make it a priority to buy two new purses this year, a smaller crossbody one and a larger black or metallic option. The small purse will come in handy when I’m doing a lot of walking and don’t want to carry a heavy bag, while the larger purse will offer some variation from the two bags that I’ve been carrying most days over the past couple of years. Once I purchase the two new purses, I may opt to let go of some of my lesser-used bags later this year.

Repeat Items from Summer “Top Fifty-Five”

Interestingly, there are ten items in my cool weather capsule that were also featured in my summer “top fifty-five” collection. I didn’t intentionally try to have any crossover between the collections, but I also didn’t set out to avoid overlap, either. The repeat items can be broken down into the following categories:

• 1 pair of pants
• 3 short-sleeved tops
• 3 cardigans
• 1 pair of shoes
• 2 purses

Here’s a look at the ten repeat items:

Ideally, I would have even more overlap between my two collections, as I live in a temperate climate without the large temperature variation that many other areas experience. But I’m happy that there’s any crossover at all, as I used to dress in completely different pieces in summer versus the rest of the year. But what this means is that I could easily get by with only 100 items in my out-and-about wardrobe for the entire year, including shoes and purses. Add in a medium-sized jewelry and accessory capsule (maybe I’ll write about that soon, but I probably won’t need a full fifty-five pieces!) and I’d be good to go!

Conclusion

Of course, I have more items in my wardrobe than what I’ve shown in my two “top fifty-five” collections, but it would be a worthy goal for me to reduce the size of my out-and-about wardrobe to around a hundred pieces. I wear my at-home items far more often anyway – every day versus maybe three or four times per week. I’ve finally curated a workable at-home wardrobe, so maybe I should do a “top fifty-five” post about that section of my closet as well. Those clothes usually aren’t as interesting and exciting as what I wear out and about, but I’ve been able to incorporate more of my personal style into what I wear at home, while still placing a priority on physical comfort.

Overall, I’m glad I decided to put together my “top fifty-five” out-and-about capsules, even if they’re hypothetical in nature and I’m still “allowed” to wear other things, too. It was helpful to take the time to select my top pieces and evaluate why other items didn’t make the cut. In my next post – part two, I’ll delve more into that topic, as I share what I learned about my cool weather wardrobe through engaging in this exercise. I’ll also write about how I hope to evolve my “not summer” wardrobe over the next few months and leading up to the next time the cooler temperatures roll around. In a future post, I’ll revisit my 2021 “top fifty-five” summer selections and share how I’ll likely vary them for summer 2022.

Your Thoughts?

Now I’d like to hear from you… Below are a few questions that you can choose to answer if you wish, but I also welcome your chiming in with any other feedback you have regarding this post.

• How many items would you include in a wardrobe capsule for the cooler months of the year?
• What types of pieces would be represented there?
• What are your favorite clothes, shoes, and accessories to wear when the temperatures are cooler?
• What gaps do you have in your cool weather out-and-about wardrobe that you’d like to fill?
• What are your biggest challenges with getting dressed during the winter months?
• How does your style differ in the winter versus the summer?