Shopping·11 min read

These Are the Winter Workwear Essentials Your Wardrobe Needs

Design: theSkimm | Photos: Reformation, Cariuma, Madewell
December 12, 2023

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We’ve all had those mornings when getting dressed for work is the last thing you want to do — especially when freezing temperatures already make it hard to get out of bed. Not to worry, you have us…and this curated list of workwear essentials you can mix and match until spring. From leather blazers to the perfect trousers, we’ve found everything you’ll need to look your best (and feel cozy) at the office. Job well done.

Mott & Bow

A boyfriend-style jean that still looks polished…

Other boyfriend jeans, step aside. We love that these have a slim leg, so they won’t look sloppy or overwhelm smaller frames. We also love the three inseam lengths and would wear any of the three washes. Plus, they look great paired with sneakers, heels, or booties. ($129, Mott & Bow)

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Commuting sneakers you won’t want to change when you get there…

Big news: We worked with our friends at Cariuma to create two limited-edition sneakers that combine all our favorite parts of a shoe. We’re talking comfy, cloud-like soles that feel broken-in from the get-go, sleek, wear-with-everything designs, and natural, eco-friendly materials. They’re a must-have for winter — and beyond. (We tested them ourselves just to make sure.) Pro tip: Grab them while you still can. (From $89, Cariuma)*

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The cashmere cardigan we can’t get enough of…

A few of our editors have this and they swear by it. Not only does it come in four timeless colors, but it’s also incredibly versatile. It’s thin enough to take to the office during spring and summer, but since it’s cashmere, it’s warm enough to slip over base layers during the colder months. You can wear it as a top on its own, or you can treat it like a traditional cardigan and wear it open with a tank, tee, or lightweight turtleneck underneath. It’s a splurge item, yes, but it’s so ideal for year-round wear that it’s worth it. ($298, Reformation)

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A classic riding boot you’ll wear for years…

Riding boots will never go out of style. Especially this pair by Frye, which — we can personally vouch for — are one of the sleekest pairs we’ve ever worn. The leather is soft, supple, and only gets better with each wear, and they look great worn with dresses, skirts, or over skinny jeans (yes, they’re having a comeback). The best part? They have a zipper on the side, so you won’t show up to work sweating from trying to pull them on. ($398, Frye)

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Ann Taylor

A houndstooth coat that completes any outfit…

This tailored coat is a wardrobe nonnegotiable. It has a chic funnel neck and is made of a wool blend that will actually keep you warm on your way to the office. It looks just as good with dress pants and a turtleneck as it does layered over a party dress, and the houndstooth pattern is truly timeless. ($119, Ann Taylor)

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A leather blazer that’s worth the investment…

If you ask us, a leather blazer is a nonnegotiable for winter office ’fits, since it layers so easily with a turtleneck, bodysuit, or sweater. This one has an oversized, menswear-inspired silhouette, which makes it timeless, but it tucks at the waist for structure. The buttery leather makes it look vintage, and while it’s pricey, you’ll never stop finding new ways to wear it. If you’re looking for something that’s less of a splurge, we love this faux-leather version. ($568, Madewell)

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A thick cardigan that comes in so many colors…

We recently scooped up this jacket-style sweater on a trip to Europe, and we’re obsessed. It buttons up the front with big tortoise buttons, has a collar, and wears well as a shirt or layered with something underneath. It comes in 23 colors, including a few patterns, so take your pick. ($170, Sézane)

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A cashmere crewneck that fits perfectly…

This cashmere sweater is slightly shrunken, so it hits right at your hips, making it just right to pair with your favorite jeans. It looks good under a blazer and comes in several bright colors. Just add a classic belt and booties, and you have an entire outfit. ($118+, J.Crew)

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A sweatshirt you can actually wear to work…

If the pandemic taught us anything, it’s that polished sweatshirts do exist, and Anine Bing makes some of our favorites. This one comes in a gorgeous neutral and looks great with jeans for a casual day or dressed up with trousers and heels. It’s 100% cotton and has a soft, lived-in feel from the first wear. ($200, Revolve)

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Abercrombie & Fitch

Trousers that look way more expensive than they are…

Abercrombie has done it again. Though we love their wide-leg tailored pants, these trousers with a tapered leg definitely deserve a spot in your work wardrobe. The high-rise fit is perfect, the front pleats are classic, and the cream color would look so good with a full winter-white outfit. Get both colors, why not? ($90, Abercrombie & Fitch)

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Abercrombie & Fitch

A long-sleeve tee that’s easy to tuck in…

Is there anything worse than maneuvering your day with a shirt that won’t stay tucked? You’ll have no such problem with this one, since the lightly compressive fabric will hug your body and stay put. It’s a seamless layering necessity and will keep you warm under a sweater as you head to the office. ($45, Abercrombie & Fitch)

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A pair of cargo trousers we can’t stop wearing…

While we may have originally purchased these strictly as work pants, these trousers have quickly become our go-tos for any occasion. We’ve worn them on a date, shopping on the weekends, and even to a baby shower. The magic is in the combination of the cinched high waist and the wide leg; it makes any outfit feel put together without being too stiff. It’s a model-off-duty look for everyday life. ($225, Net-A-Porter)

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A crisp button-up that’s a closet essential…

A white button-up is a classic for a reason. This one has a relaxed fit, so it pairs well with jeans and even looks cute worn as an overshirt with your favorite tee underneath. You’ll never get tired of styling it, and it comes in five colors. Grab a few so you’re set for the whole year. ($88, Everlane)

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A shirt dress you can dress up or down…

We love to see a dress like this that’s essentially a blank canvas for accessories. Throw this on with tights and loafers (see below), and tie a sweater around your shoulders to go full prep. The next time you wear it, pull on heeled knee-high boots and add a menswear coat to channel Taylor Swift. The possibilities are endless. ($148, Anthropologie)

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Free People

Platform loafers you’ll wear for multiple seasons…

Besides being downright stylish, these loafers are also comfy. We love the menswear-inspired look with the little tassels on top. Pair them with jeans in winter, then skirts and dresses in spring. Don’t forget the frilly socks. ($190+, Free People)

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A turtleneck that’s great for layering…

Time and time again, we’ve thrown on this turtleneck with jeans and felt incredibly polished with minimal effort. It’s made of a soft, ribbed cotton that’s breathable, so you won’t be sweating when the heat turns on. It comes in 10 colors. ($50, Everlane)

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A slip skirt that’ll never let you down…

There’s something about a slip skirt that’s so effortlessly chic. We love J.Crew’s, with its midi length and elastic waistband so you won’t be uncomfortable sitting at your desk all day. It comes in six colors, including a stunning hot pink. Life’s short, wear the fun skirt. ($79.50, J.Crew)

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*This denotes a sponsored section.

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