Chic on the Street! Shop Our Favorite Recent Street Style Looks, From Katie Holmes to Kendall Jenner

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Slouchy leather bomber jackets, statement sweaters, funnel-neck outerwear, sleek black boots–what do all of these winter hero buys have in common? They’re taking up some serious real estate in our shopping carts, while also making their mark on fashion girls from all over. As we wait with baited breath for fall/winter 2025 fashion week to commence in February, some of our favorite celebs, from Katie Holmes and Kendall Jenner to Bella Hadid and Zoë Kravitz, have been stepping out in chic wears fit for the season’s dropping temperatures–spotlighting both the pieces that most-wanted to those elevated wardrobe essentials we know and love.

Vogue’s Top 10 Street Style Standouts:

• The Statement Sweater: Banana Republic lightweight cashmere V-neck sweater, $150
• The Slouchy Leather Bomber Jacket: Zara faux leather high collar jacket, $60
• The Sleek Black Boot: Aeyde Torin leather knee boots, $755
• The Velvet Blazer: J.Crew Alexandra blazer in velvet, $278
• The Chic Jean: Frame The Hang jeans, $268
• The Cropped Trench Coat: Pixie Market contrast corduroy cotton jacket, $269
• The Burgundy Bag: The Row Dalia baguette bag, $1,990
• The Quilted Shell Jacket: Guest in Residence quilted liner jacket, $795
• The Cozy Clog: Birkenstock Boston soft footbed clogs, $160
• The Snuggly Shearling: Max Mara The Teddy Bear Icon coat, $4,490

Now don’t get us wrong, dressing for winter’s grueling weather can be notoriously challenging for our wardrobes. One day you can expect a biting chill in the air where the sun shines especially bright, and the next, wintry mixes will be falling down with fervor, calling for a long down coat and a sturdy lug-sole boot. That said, this season has been uncharacteristically warm in New York City, so some of the looks below resemble more of our transitional capsule wardrobes where lightweight trench coats, great denim, and polished penny loafers steal the show. To steer you in the right sartorial direction, the street style scene has come to your rescue, providing easy, yet elegant outfit formulas suit for every kind of winter day–freezing or not.

Below, 37 fashion week trends worth adding to your fall shopping carts.

The Argyle Sweater With a Capacious Tote Bag