6 Ways to Style a Letterman Jacket

Now that it’s getting colder, it’s time to inject some vintage-inspired style into your fall wardrobe. Don’t settle for a hoodie or a pea coat when you can set yourself apart with a stylish and sporty letterman jacket. Gone are the days when this look was reserved for only the highest achieving jocks. Now, anyone can rock a letterman jacket, and no matter what your signature style is, the letterman jacket can be flawlessly incorporated. Here’s a few ways to try it:

Classic All-American:
Classic All-American

Not much of a stretch here, as this look has been synonymous with the letterman jacket since its inception. Keep things squeaky clean with light skinny jeans, a plain top, and let the jacket be the focal point.

Boho accessories:
Boho accessories

You don’t have to go preppy to make the letterman jacket work for you. Incorporate your jacket with patterned scarves and a few funky accessories to make this look your own. Pair with plain black pants and a neutral top.


Take sporty style to the streets with the ultimate in sports apparel. Let the jacket speak for itself and stick to monochrome colors. Keep things comfortable by showing a little leg in a nice pair of shorts and couple it with a breezy, loose-fitting top.

Feminine meets Masculine:
Feminine meets Masculine

Just because the letterman jacket is innately sports-related doesn’t mean you’ve got to switch up your feminine style. Go for the slouchy “boyfriend” look by pairing a flirty skirt with your boxy letterman jacket. Bonus points if you manage to match your lipstick to your chenille patch!

Throwback grunge:
Throwback grunge

Fashion is cyclical, and we’ve been experiencing a 90s revival for a few years now with high-waisted pants, babydoll dresses, crop tops and dark lipstick coming back in to fashion. Pay homage to that bygone era with a grunge inspired look. Pair high-waisted jeans with a crop top or flannel shirt tied at the wasit. Top with your letterman jacket and finish the look with a classic pair of Chuck Taylor’s.


Even if you identify more with the alternative crowd than the classic All-American jock, you can rock a letterman jacket. Play up the juxtaposition of styles by pairing this preppy classic with ripped jeans and edgy jewelry.

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