The high-rise flare updates its ’70s heritage with polished styling—pairing with sleek blouses, tailored blazers, and slim knits. Plus, a slim-to-wide silhouette is flattering on any figure, accentuating the waist and elongating the leg.

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SIMILAR: FRAME DENIM Le Flare De Francoise Flared Jeans

Modernize the super-feminine, always-demure high-neckline by styling it in fresh ways—in this case, tomboy trousers, sleek heels, and a red lip.

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SIMILAR: PHILOSOPHY DI LORENZO SERAFINI Lace-Print Chiffon Blouse / ISABEL MARANT ÉTOILE Senda Crop Suit Trousers / MANOLO BLAHNIK Suede BB Pumps

OTK boots are a great way to keep chic and warm in chillier temps (extended coverage!). Pair them with a midi-skirt—the slit seen here adds wow-factor.

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SIMILAR: GIANVITO ROSSI Suede Over-The-Knee Boots / JI OH Wrap Pencil Skirt / THE ROW Ghent Sweater

The sporty staple makes a statement this season thanks to fashion-forward details like luxe textures, intricate embroidery, unexpected colors, and playful patchwork.

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SIMILAR: DRIES VAN NOTEN Cherry-Blossom Jacquard Bomber Jacket / LUCIEN PELLAT-FINET Leather-Skull Bomber Jacket

Just because the temperature’s dropping doesn’t mean the sun is hibernating! Add a playful vibe to your fall wardrobe of knits and leathers with a pair of retro-inspired round frames with brightly colored lenses.

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SIMILAR: MOSCOT Faye Sunglasses

Details like clasps, drawstrings, belting, and zippers elevate everyday trousers and embrace this season’s understated utility vibe. Crisp, structured separates add a polished, office-appropriate finish.

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SIMILAR: DRIES VAN NOTEN Crop Palese Cargo Pants / THE ROW Petra Poplin Blouse

Backpacks continue to mature this fall, with supple leathers, exotic skins, and luxe finishings making handsfree a chic option for day or night. From The Row to Proenza Schouler, there’s a variety of styles and designers to choose from.

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SIMILAR: ILLESTEVA Charlie Mini Backpack

8. Raw Hem

For a sophisticated spin on distressing, this season’s raw hems strike the perfect balance—just undone enough to be nonchalant with clean lines keeping the look refined. Simon Miller, Pas de Calais, and ATM all embrace artful fraying.

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SIMILAR: SIMON MILLER Frayed Graham Jacket

9. Culottes

Calf-grazing silhouettes are perfect for tricky trans-seasonal weather with their breezy, partial coverage easily transitioning from warm days to cool. From basic to bold, relaxed to structured, they’re versatile style stars that your wardrobe is begging for.

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SIMILAR: RAQUEL ALLEGRA Denim Culottes

Nothing welcomes fall more than a roomy knit, and luckily they go with everything from mini-skirts to boyfriend jeans. And with delightful offerings like Ryan Roche‘s sumptuous cashmeres and The Row’s luxe-minimalism, get ready to make room in your closet.

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SIMILAR: SPENCER VLADIMIR Bouclé-Striped Oversized Cocoon Sweater

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