I’m sure it won’t come as a surprise to anyone that I, someone whose career revolves around fashion, have something of an obsession — well…problem — with shopping. I can’t pass up a vintage bargain or a sale and am capable of convincing myself that any overpriced item I like is a worthwhile investment — which is why my 2023 resolution was to buy less.

No more “oh, this will be perfect for that one single event” dresses or shoes I can only stand in for an hour; this year’s closet additions were guided by the goal of outfit repeating. And I’m here to report that when you’re being intentional about what goes into your wardrobe, rather than impulsive, you end up with pieces you actually want to re-wear. This winter, seven items have been in my weekly rotation, including super-warm knits and trousers that instantly elevate all of my wardrobe basics. 

7 Winter Items I’m Wearing on Repeat

Gap CashSoft Midi Sweater Skirt

When Gap came out with its CashSoft collection, which it advertised as being an affordable alternative to cashmere, I couldn’t wait to test it. I opted to try the brand’s midi sweater skirt because I loved how it brought warmth to a style I already knew I loved. The A-line silhouette hangs perfectly on my body without clinging or accentuating panty lines and goes with everything from basic white T-shirts to cozy sweaters and more elevated blazers. And, yes, it’s seriously soft. Unlike a lot of affordable knitwear, it doesn’t pill (or, at least it hasn’t yet for me), doesn’t irritate the skin, and is breathable yet warm thanks to its cotton blend. Honestly, the skirt feels so good that even when I’m working from home — and could be in my pajamas — I slip this on instead. Shoppers love it, too, deeming it “very versatile” and a “wardrobe staple.”  

Everlane the SuperFuzz Alpaca Crewneck Sweater

Everlane might have introduced me to my new favorite sweater; its SuperFuzz Alpaca Crew is unbelievably cozy, just the right amount of oversized, and stylish. Oftentimes “fuzz” loosely translates to being itchy and prone to shedding, but that hasn’t been the case with this sweater, which feels like your favorite pair of cozy winter socks or blanket and doesn’t transfer onto any of my other clothes. I have this in the red striped style — which I dress up with a matching red purse and cherry-inspired Mary Janes (you’ll read more about them below) — but it’s also available in four other colorways, including classic neutrals and even a chocolatey argyle print. 

Rothy’s the Square Mary Jane

The shoes in question! For a number of reasons, it’s rare that I go a day without sliding on these Mary Jane flats from Rothy’s, a Meghan Markle-worn brand. One, they’re easy to put on and stay in place thanks to their stretchy quality, so even when I’m just making a quick coffee run in my sweatpants or taking the trash out, these are what I reach for. Two, they’re beyond comfortable — I’ve walked over three miles in these without a single ache or blister. And three, they’re really cute. Mary Janes have been in for a while and these are probably the most comfortable and stylish pair I’ve tried. The silhouette is classic, while the red color adds a darling, festive touch to just about any look I throw together. And when it’s cold, all you need to do is add a pair of socks à la Hailey Bieber.

M.Gemi the Francesca Grande Bag

In the winter, I have to make the switch from small shoulder bags to crossbody purses simply because their arm holes usually aren’t wide enough to accommodate the season’s needed layering. And this year, I’ve opted for M.Gemi’s Francesca Bag, which is made of soft, high-quality Italian leather and available in four colors: saddle brown, classic black, white, and cobalt blue (my go-to for a pop of color). I love how versatile this bag is — when I want to dress it up, I simply remove the strap and wear it as a clutch — and that it brings unique elements to the world of often basic crossbodies, like a loop closure that doubles as a wrist strap. Shoppers have even called it “elegant” and versatile, noting that it “works with casual or dressy clothes,” and note that it’s the “perfect” size for “carrying a wallet, cell phone, and some essentials without feeling weighed down.”

Gap Vintage Soft Hoodie

In case it’s not clear, Gap stole my heart this season, and this hoodie was the first thing I fell in love with. I know I said no to impulse purchases this year, but after seeing how chic Jennifer Lawrence looked in a hoodie with a long trench coat, I immediately added this lookalike to my cart. Luckily though, it ended up being worth it. This might seem like an exaggeration, but when I say that this is the best hoodie I’ve ever owned, I mean it. The fit is perfect and flattering (well, as flattering as a hoodie can be); it’s neither too tight nor too oversized and hits right at my hip bones. And customers agree, with one person writing that it’s “not too baggy and is the perfect length.” It’s also warm, soft, and washes well, without fading or shrinking.

Madewell the Harlow Wide-Leg Pant in Satin

Madewell’s pants — from its famous denim to its straight-leg trousers — have long been a favorite of the InStyle team, so it’s not shocking that the brand’s shopper-loved Harlow pants have become one of my winter go-tos. The Harlow trouser, which features a high waist, pleats, and wide leg, is a staple of the brand, but this winter, Madewell launched a satin version I can’t stop wearing. It’s shiny without being gaudy (the finish is luxe-looking), doesn’t cling, and instantly elevates all of my basics — it’s a cool-girl must-have. And shoppers love how “beautifully made” the style is, with one person writing that the satin “fabric is the perfect weight: substantial, not flimsy!” 

Everlane the Knee-High Banana Heel Boot

I’ve been on the hunt for the perfect knee-high boot for years now. As someone with wider calves, I’ve really struggled to find styles that comfortably fit my legs, but Everlane managed to seriously impress me with its Banana Heel Boots. I’ve tried pairs that either just don’t fit my legs — like they stop pulling up/can’t get over my calves — or squeeze so tightly, I’m worried about my blood flow, but this style is loose enough that I don’t feel constricted, even with thick tights or socks underneath. But despite that, it’s not an oversized boot; it’s streamlined and chic, featuring an elegant pointed toe and skinny heel. What’s more, my feet don’t dread these; I wore them on a night out where I walked about a mile and stood for over three hours, and I didn’t end my night with blisters or aches. “These have become my holy grail boots,” wrote one fan, explaining that “the leather is beautiful, the shaft is the perfect width (and [they] have muscular calves), and the pointed toe is both perfectly on-trend and timeless.”