8 Day-to-Night Looks to Shop, Inspired by Kaia Gerber’s Best Outfits

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Pleats, Please!

A pleated mini skirt always tends to give us those fall feels, evoking memories of school, but this idea doesn’t have to be reserved just for the Gen-Zers. By pairing the skirt with an oversized blazer, this undone look is more Parisian street style than school uniform (and for those who might scoff, black and navy blue can certainly be worn together). Adding a clean, leather knee-high boot and designer shoulder bag takes this look straight from day-to-night. Once those winter temps hit, simply add hosiery. It works both ways.

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Luck Be a Lady

A good coat is a cold-weather must and Gerber proves this time after time; afterall, it is probably the most worn item in your wardrobe during these months. Make yours similarly the star, starting with one in a deep navy colorway in a ladylike silhouette. It’s a welcome way to switch up your traditional winter outerwear game—and will keep you from wearing black all the time. This similar option from Banana Republic is made from 100% wool, can be worn straight to the office with the sheerest of black tights, loafers, and your carryall tote bag, then seamlessly transitions for a night out with strappy pumps and a sleek clutch.

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No Sweat

Nothing feels quite as good as your favorite sweatshirt, and when paired with a pair of perfect, baggy jeans, the look is chef’s kiss. However, Gerber keeps to her own style codes when accessorizing this look for everyday. Rather than wearing a somewhat expected sneaker with this classic pairing, she opts instead for a simple, ballerina flat, her personal shoe style du jour. A roomy, hobo bag in a luxe brown is not only on-trend, but leans into the overall Y2K-mood she has going on. The trucker cap (which promotes her book club, Library Science) and oversized sunnies only amplify the early aughts feel.

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Suiting—The Evening Edition

No matter your age, never estimate the power of a well-cut, black suit. The 23-year-old model understands its everlasting importance (cough it up, perhaps, to one very stylish Mom). Still, Gerber gives the essential, two-piece suit her own twist, making it evening-friendly with a sheer and sexy, cropped top underneath and sky high, pointy pumps. It’s the perfect combo for a night out on the town, but can also be turned to office-appropriate in a flash by swapping out the underpinning. Try anything from a crisp, white button-down to a slim, turtleneck top.

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All About the Indigo

‘Tis the season to really deep dive into denim, so that means loading up on all the best jeans, jackets, and more. Gerber’s key to nailing the double denim look is blending different washes. She keeps things tonal with deep indigo hues underneath, using loose-fit jeans and a cropped baby tee as primers. This darker palette beneath leaves room for a lighter wash to enter the mix on top. Again, she reaches for her perpetual besties in the accessories department (black ballet flats and AirPods Max headphones) to keep things commute-friendly.

Agolde

Luka cropped denim jacket

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Contemporary Boho

There’s no escaping the Chloé effect, and even Ms. Gerber isn’t immune to the “New Boho” style era. Whereas on the street, Gerber’s off-duty style gravitates towards casual and cool, these days, her dressed up looks have a slightly more romantic approach. A sheer, lace blouse from the Parisian house brings home the bohemian idea, while a tailored trouser pant offers wearability. Chunky gold jewelry, signature, strappy black pumps (and even a pair of geek-chic frames) finish things off with plenty of modern flair. Consider us influenced.

Chloé

cape-effect knotted blouse

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The Image Direct

Outfitting for the Elements

The colder seasons are all about layering, but that doesn’t mean you can’t look polished. Gerber demonstrates how simplicity can be your best friend—which means stocking your closet with everyday essentials, such as an oversized coat with room to layer, clean-cut jeans, and a cozy, cashmere sweater (thrown effortlessly over the shoulders, of course; it’s the supermodel-approved way). Separately, these pieces hold their own as modern, wardrobe necessities, but together, they are unstoppable.

The Frankie Shop

Gaia double-breasted coat

Tibi

Classic denim Barry jeans

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Literary Chic

Fond of the written word, Gerber can often be found playing up her love of literature with an element of bookish quirk in her everyday style. Whether that be quite literally, as seen through her array of graphic T-shirts and ball caps, or figuratively, in this case. Cardigans and plaid motifs might herald images of traditional, librarian garb, but here’s where you want to take styling notes. Leave the cardigan slightly unbuttoned sans underpinnings and choose a silky, midi skirt silhouette to keep an overall contemporary tone.

Reformation

Clara cashmere crewneck cardigan

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