Rounding up my winter wardrobe workhorses
What I've been wearing and re-wearing through the Midwestern winter
Welcome to the Esther Studio newsletter! I’m Carly, PhD, a marketing professor and artist living in the Midwest. I like talking about personal style, and I spend a lot of time making jewelry. If this sounds fun to you, keep reading and consider subscribing so we can see more of each other!
As the first signs of spring tentatively (tentatively!) reveal themselves in the Midwest, I’m feeling some anticipatory nostalgia for all my favorite winter outfits. I recognize that this is not a normal feeling, but as a person who loves coziness and layering, this is where I’m at.
This winter, I’ve been working on wearing and re-wearing my favorite pieces so they get the love they deserve. I’ve also been relying heavily on some items that do their job better than anything else in my closet.
In this post, I’m rounding up my winter wardrobe workhorses so I can properly see what has, on purpose or accidentally, become my “look.” My hope is that I can use this information to prepare for a comfortable and stylish spring - even if I’m already mourning my cold-weather vibe!
Here are five items that earned their keep in my closet this winter.
1. Burgundy patent leather ankle boots
One of my core-shaking personal style revelations of this season is that I live for walkable heels. I’ve come to prefer them over my tried-and-true loafers, and I’m not quite sure what to do with this information.
I bought these ankle boots last winter. I’d been debating between the burgundy and chocolate brown, and ultimately went with burgundy because I thought they would be a nice pop of color. I quickly got a rubber sole put on them at the cobbler, and then wore them approximately once for an entire year. Embarrassing!
The guilt of this purchase weighed on me over the summer. I must have really committed to making them work this winter, because I now wear them perhaps every other day. The heel is just the right height, and they add a kind of polish to every outfit that my loafers just can’t.
I will say: the burgundy was a mistake. If I could go back in time, I would order the chocolate brown. I am simply not a burgundy person, and an “investment boot” was not the ideal way to learn this. But! I’ve leaned into the fact that when I wear these boots, the burgundy may not go with everything I’m wearing, and that’s part of the fun.
Note to Future Carly: How can you recreate this ankle-boot magic in the spring and summer months? Maybe a heeled fisherman sandal?
2. Navy wide-leg wool trousers
Something I haven’t talked about on the internet - but won’t shut up about IRL - is the spellbinding Banana Republic renaissance of recent years. I can remember just a short decade ago when this brand was quite dusty. As a lifelong workwear enthusiast, I’m thrilled they took a good long look at themselves and decided a glow-up was on the docket. It has worked out very well for me, particularly in the pants department.
I first tried on these lightweight, 100% wool pants while on a work trip in San Diego last summer. I was helping my friend Abby shop for professor clothes, and of course got lost in a side quest of my own. Banana’s pants usually don’t accommodate my booty and thighs, but these ones are roomy enough for two of me! They also include buttons along the inside of the waistband for you to adjust as needed. They are perfect.
They are also so, so wide. This gives them more personality than the slimmer dress pants in my closet, and for that reason I tend to gravitate towards them first. I have them in camel and gray, and I do wear them all, but if I could only pick one, it would be navy.
These pants look great with my aforementioned ankle boots, but they also work well with sneakers! I choose them when I need a comfortable option for existing at work all day, and they truly never let me down. Thank goodness for these pants, and long live Banana Republic.
Note to Future Carly: Measure all other pants purchases against these pants. If they don’t meet this standard, don’t buy them, as you will not wear them.
3. Silver perforated leather tote bag
I let my appreciation for metallics, particularly silver, percolate for a long time before taking action. I know this is one of those things that would have never been on my radar if it weren’t for the trend cycle, so in those cases I always “add to cart” with caution.
I thought long and hard about this perforated leather tote bag, but since adding it to my wardrobe in the fall, it has become my near-daily choice for work. I’ve noticed that silver works beautifully as an almost-neutral. It’s interesting and eye catching, and it goes with everything. For that reason, my other leather tote bags (taupe and navy) have actually become a bit dusty!
This is one trend I will happily wear long after it’s popular.
I had a fun time making two bag charms for this cutie. The first is a long chain that I decorated with silly little charms, including three dinosaurs. The other is a long dangly clip-on. I think they add such a nice level of personalization while also leaning into the not-so-serious fun of the silver.
Note to Future Carly: You probably don’t need another leather tote bag! This one will work all year round! But if you find yourself tempted to buy another leather tote bag, which you will, at least make sure it’s a fun one.
4. Blue floral midi skirt
Again and again, I choose this skirt over others in my closet. I think it might have something to do with the slightly shiny fabric that reads a bit fancier than my more matte options. The colors go with pretty much anything else I want to wear. As with anything I love, I can dress this skirt up or wear it more casually.
I’ve been leaning into its dress-up capabilities lately. My favorite recent look involved brown knee-high boots, a striped pussy-bow blouse, and a ruffle vest. The whole thing was on the maximalist side, but that’s what I loved about it. Just because the skirt is already “busy” doesn’t mean I need to pair it with more subdued friends.
I’m going to wear this skirt until it falls apart. In fact, it’s already falling apart, but as long as no one looks closely, we’re good.
That’s the one thing that’s disappointed me about this skirt. Almost immediately after buying it from a normally reliable retailer, I noticed the stitches coming undone at the waistband. Over time, I’ve also seen some snags in the delicate fabric. This has taught me that not everything from my favorite brands will be a winner, and to be critical about quality on a piece-by-piece basis.
Note to Future Carly: When this floral midi skirt finally bites the dust, you can’t just replace it with any ole floral skirt. It should be on the fancier side and the color palette should go with everything.
5. [Nearly] indestructible black pantyhose
This is a deeply boring entry, but I have to give a shoutout to my [nearly] indestructible black pantyhose. I have a few pairs from a Canadian brand, Sheertex, and they have been well worth the $25 price tag (on sale).
I think pantyhose are a somewhat divisive fashion choice, but since I’ve been wearing skirts all winter, they’ve been essential for me, and my cost-per-wear on these babies is quite low as a result. I love a slightly sheer option because it breaks up the opacity of a wool-skirt-and-leather-boot combo.
I was deeply skeptical about Sheertex’s claims that their pantyhose are “the world’s strongest tights,” but after wearing them for two years now, I can say this is a pretty accurate statement. I’ve never experienced a dreaded “run.”
The worst thing that’s happened - and I’m still not over it - is that a thick tag on one of my long wool coats rubbed against one of my legs and made a bit of a mess. I can still wear this pair under knee-high boots, but it was a good reminder that “the world’s strongest tights” have their limits.
All of this is to say, if you’re a pantyhose person and you’d like to buy fewer pairs overall, this brand is a great option!
Note to Future Carly: Next winter, you will be tempted to buy more pairs of Sheertex tights in all of the fun colors and fun patterns, but you will always come back to your simple black ones, so don’t waste your money!
I think I’m ready for you, spring!
As much as I’ve loved getting dressed this winter, and as much as I’ll miss my winter workhorses when the weather changes, I do think it’s time for all of us to enjoy some sunshine and levity.
One thing I can take away from this winter is that it’s okay, and it’s for the best, to re-wear my favorite pieces again and again. This is how I’ll end up knowing myself and developing my signature looks. If something wears out, I can replace it. If something looks worn, that just means I’ve gotten my money’s worth.
I’m so excited to see what my workhorse pieces will be for spring and summer! Over the past few years, I’ve worked hard to find reliable pieces and looks for these seasons. While I still feel a bit lost without my winter layering, it’s getting easier to get dressed in warm weather.
Thanks for spending time with me this week!
Don’t go yet! Let me know in the comments…
What were your most-worn pieces this winter?
What are you looking forward to wearing this spring and summer?