Have you ever seen a Kaia Gerber outfit and not wished you owned everything she was wearing? Didn't think so. She has mastered the relaxed-yet-cool vibe that her famous mom, Cindy Crawford, has always been known for. Of course, her latest outfit is no exception. Photographed holding hands with Pete Davidson on a getaway in upstate New York, Gerber just wore my ideal November outfit: a cozy beanie, striped sweater, leather coat, and lace-up boots. The flat boots, in particular, are the perfect practical choice for a chilly fall day.
As we've mentioned in several stories, leather is a major trend right now. (Yes, there are lots of vegan options!) The street style set loves to wear leather head to toe, but as Gerber just showed, a cute jacket is all you need to pull off the look. Bonus points if you match it with your boots. Scroll down to see Gerber's day-date outfit, and shop similar pieces.
Shop the Look
Next, Kate Middleton wore the $30 Zara item everyone will want.
-
FYI: This Shirt Trend Makes Jeans Look So Much PrettierYes, pretty.
-
The New Rules of Summer Denim: No Rips, No Fray, No FussSee the full set of rules inside.
-
The Anti-Trend Shoe Style All of Your Favorite Celebrities Have in Their ClosetsClearly, it's a chic classic.
-
The Anti–Skinny Pants Trend Cool New Yorkers Are Quick to Ditch Their Blue Jeans ForBuh-bye.
-
Every Cool New Yorker Knows These Anti-Trend Flats Look Better With Jeans Than Boots and SneakersClassic and chic.
-
I Called the Cuffed-Jeans Trend—7 Shoes Fashion People Are Wearing With the Chic Denim StyleStyle the jeans like a fashion person.
-
Stop the Search—We've Discovered the Cool Denim Trend Every Fashion Person Will Be Wearing Throughout 2025And 2026.
-
It's Spreading: Every Day, Another Chic L.A. Fashion Person Is Seen Wearing This Black-Pant Trend With Ballet FlatsFrench women also approve.
