1A Structured Coat + Sweatpants
Christian Vierig//Getty ImagesTruthfully, I'm still kinda recovering from ringing in the New Year, and that can only mean one thing: sweats. An oversized black coat with structured details makes this 'fit look intentional and not just something you threw on last minute, even though you def did.
2An Unbuttoned Maxi Dress + Layered Mini Skirt
Edward Berthelot//Getty ImagesGet twice as much mileage out of your maxi dress by unbuttoning halfway and letting your mini skirt peek through. It's cheeky in all the best ways. This works really well especially if the maxi is form-fitting since it basically doubles as a super-long cardigan. Chic, right?
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3Head-to-Toe Cream
Edward Berthelot//Getty ImagesStart out the year with a clean slate (literally) with a full cream ensemble. Not only does it feel super sophisticated, but it's also super versatile. It's a foolproof look that gives major "so fresh and so clean" vibes.
4A Blazer Dress + Red Tights
Mauricio Santana//Getty ImagesWhy not take that structured blazer dress from the back of the closet and shake things up by adding a pair of cherry-red tights? A pair of pumps and some edgy accessories take this look from office to drinks in a flash.
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5An Oversized Sweater + Leggings
Edward Berthelot//Getty ImagesThe only thing better than being in leggings all day is being cute in leggings all day. Seriously, layering on an oversized sweater not only looks super chic, but also means nobody will know that you're secretly extremely cozy. Bonus points if you match your sweater to your leggings, shoes, bag, etc, etc.
6Mismatched Leather
Christian Vierig//Getty ImagesHead-to-toe leather is pretty much as universally cool as it gets, but mixing things up by pairing pastel leather with black takes things to a whole new level.
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7Leopard as a Neutral
Jeremy Moeller//Getty ImagesOK, so maybe animal print isn't groundbreaking, but it's a classic because it simply works. Don't fix it if it's not broken, right? Sport your favorite leopard-print piece as a neutral by matching the color palette (like with a white tank top, beige coat, and cream sneakers, as shown here). Then add a pop of color with your accessories.
8An All-Black Ensemble + Statement Accessories
Edward Berthelot//Getty ImagesWhen you're truly stumped on what to wear, take the pressure off by opting for an all-black ensemble and letting your favorite accessories steal the show.
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9A Matching Sweater Set
Edward Berthelot//Getty ImagesNothing—and I mean nothing—is easier to wear than a matching set. It's the perfect go-to outfit when you don't want to think about what to wear, and it always looks polished, no matter the occasion. Add some cool accessories (like a bag with standout hardware and matching jewelry) to add some edge to your look.
10A Black and White Layered Preppy Look
Rachpoot/Bauer-Griffin//Getty ImagesA crisp white button-up quite literally goes with everything in your closet, but if you're in the mood to switch things up, why not channel your inner Blair Waldorf with a preppy layered look? Odds are you already have most of this outfit recipe: a white button-up, a black sleeveless top, and a pair of killer boots. Put them together and you have a chic twist on a classic.
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11A Belted Blazer + Easy Denim
Neil P. Mockford//Getty ImagesOn days when you truly have no idea what the vibe is going to be for the function, you can never go wrong with a blazer and jeans. Add a skinny belt to pull it all together.
12An Oversized Coat + Baggy Jeans
Jeremy Moeller//Getty ImagesJeans and a tee don't have to be basic. Make a statement with an oversized coat (obsessed with this chocolate brown one!), a fitted white tee, and relaxed light-wash denim cinched with a belt. It's the perfect balance of laid-back comfort and elevated style—a fresh take on your everyday uniform.
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13A Glitzy Dress + Boots
Edward Berthelot//Getty ImagesStill feeling festive? I'll say it: Glitz works all year round. Consider repurposing your fave holiday mini-dress for a January event by pairing it with knee-high boots. Not only does this combination offer welcome winter coverage, but it's also perfectly dressy for those spontaneous evening plans—whether it's last-minute drinks or an impromptu dinner out.
14A Hoodie + a Full Skirt
Valentina Frugiuele//Getty ImagesYour favorite hoodie can instantly make any outfit more comfortable. Even a plaid skirt gets a cool street-style edge when paired with a cozy hoodie. If this feels a bit out of your comfort zone, start with a simpler hoodie design—it'll keep the look from feeling too busy while still capturing that effortlessly chic vibe.
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15A Cozy Sweater + Maxi Skirt
Edward Berthelot//Getty ImagesFor those days when you want nothing more than to feel cozy and bundled up, a sweater and maxi skirt might not sound like the obvious choice – but trust us, it absolutely works. Not only is this combination foolproof, but you can also sneak some thermal leggings underneath your skirt for those particularly frigid days.

Belle Bakst is a NYC-based fashion editor and content creator. Her work has been featured in Cosmopolitan, InStyle, Harper's Bazaar, Brides, and more. When she's not researching this season's best shoes, you can find her vlogging a sample sale, or thrifting in Manhattan. Follow @littlefashionstylist on Instagram and TikTok for outfit inspo, vintage jewelry hauls, and the occasional Bergdorf Goodman selfie.
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