Inspired by timeless Ivy League style, this season the classic prep school look is anything but, thanks to design houses like Prada, Louis Vuitton, and Dries Van Noten. This time-honored trend gets a high-fashion update for fall with cutting-edge cuts, bold colorways, and unexpected pattern play — think reimagined checks and stripes, streamlined letterman jackets, and exaggerated button-ups. Here, we’ve selected a few that make the grade.

Fluffy Bucket Hat, $665, at Saint Laurent at Somerset Collection, 2801 W. Big Beaver Road, Troy; 947-237-3088; saintlaurent.com.

Velvet Canyon The Stranger Sunglasses, $195, Eugenie, 1400 Van Dyke St., Detroit; 313-556-2110; eugeniedetroit.com.

Vagabond Shoemakers Dorah Tall Boot, $250, Eugenie, 1400 Van Dyke St., Detroit; 313-556-2110; eugeniedetroit.com.

MM6 Maison Margiela Long Sleeved Shirt in White, $530, at Coup D’état, Detroit; 313-782-4480; shopcoupdetat.com.

Leather Accent Check Tweed Skirt, $3,200, at Louis Vuitton at Somerset Collection, 2801 W. Big Beaver Road, Troy; 248-643-8930, louisvuitton.com.

Graphic Stripes Knit Top, $1,470, at Louis Vuitton at Somerset Collection, 2801 W. Big Beaver Road, Troy; 248-643-8930, louisvuitton.com.

Backpack, Price Upon Request, Prada (coming soon to Somerset Collection); prada.com.

Piercing iPhone Case in Natural Smooth Leather, $625, at Balenciaga at Somerset Collection, 2801 W. Big Beaver Road, Troy; 947-225-2727; balenciaga.com.

Justine Clenquet Rose Hair Clip Set, $65, at Coup D’état, Detroit; 313-782-4480; shopcoupdetat.com.

Multi Buckle Monk Strap Shoe, $498, at Tory Burch at Somerset Collection, 2801 W. Big Beaver Road, Troy; 248-458-1307; toryburch.com.

This story originally appeared in the September 2024 issue of Hour Detroit magazine. To read more, pick up a copy of Hour Detroit at a local retail outlet. Our digital edition will be available on Sept. 6.