Cadet Hats Are The Next Big Accessory for Autumn — Here’s How to Wear Them

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This fall I’m swapping my baseball caps for a new trending accessory — a cadet cap. The grunge-tomboy style hat was a staple in my wardrobe in 2003, so when I saw that it was making a comeback for the autumn season, I could not be more ecstatic. Apparently, my early-2000s wardrobe knew what it was doing all along.

With its flat top, short structured brim, and military-inspired shape, the cadet hat has a distinctly nostalgic silhouette that feels straight out of early-2000s street style. However, this time around, it feels a little more polished and perfectly suited for fall.

It’s the kind of accessory that can instantly make a simple outfit feel more intentional, whether you’re pairing it with an oversized sweater and jeans, a leather jacket and mini skirt, or your favorite fall coat. Below I’m sharing everything you need to know about the cadet hat trend and how to wear one this fall.

4 Cadet Hat Outfits: How to Style the Cadet Hat in Autumn

1. Bootcut Jeans + Suede Jacket +Boots + Cadet Hat

If you want to tap into the early 2000s style once more, then opt for a modern pair of bootcut jeans, a tan suede jacket, and some boots. Throw on your cadet cap, a scarf, and your favorite purse to really bring the nostalgic look together.

2. Wide Leg Pants + Olive Green Utility Jacket + Cadet Hat

I love how fresh and modern this cadet hat outfit looks. The wide-leg pants and oversized utility jacket lean into a casual take on the military style. Opting for a textured, patterned cadet hat adds dimension to the outfit as well.

3. Patterned Jacket + Wide Leg Jeans + Loafers + Cadet Hat

Leaning into an autumnal color palette in the fall is a must. I love how this outfit idea does just that, but also includes a cadet cap accessory. To recreate this look, pair dark-wash wide-leg jeans with a patterned, auburn jacket. Complete the look with loafers and socks and a cadet grey cadet cap on top.

4. Leather Jacket + Straight Leg Jeans + Loafers + Cadet Hat

Leather jackets and cadet hats are such a classic combination. It looks so chic and elevated for the fall season too. Start by throwing on your favorite straight-leg jeans, a stark black leather jacket, a black wool cadet hat, and some leather loafers. Don’t forget to grab a purse and wear some simple earrings to complete the styled outfit.

Our Editor’s Favorite Cadet Hat Picks