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Greta Hollar

Nashville, TN

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How to Style Your Denim Shorts into the Fall

August 24, 2026

This post about how to style denim shorts into the fall contains affiliate links.

Late August and early September are a strange time of year when it comes to fashion. It’s still hot like summer, but the clothing in the store says fall. So let’s have a compromise. Shorts for fall! I love my cut-off denim shorts so I’m having fun and experimenting with different ways to style my shorts for fall. Check out a few tips on how to wear denim shorts below!

How to Wear your Favorite Denim Shorts into the Fall | Greta Hollar | How to Wear Denim Shorts by popular Nashville tall fashion blogger, Greta Hollar: image of Greta Hollar wearing a Farm Rio bodysuit, denim cut-off shorts, brown leather belt, and felt fedora hat.

How to Style Denim Shorts into the Fall

Wear a Fall Top

Style your denim cut-offs with a sweater, black turtleneck, puff sleeve blouse, or a long sleeve bodysuit. I styled my shorts with a Farm Rio bodysuit. It can transition into fall beautifully and has some pretty seasonal colors in it. But right now it also pairs great with my cutoffs! Shop some similar bodysuits/tops that are available below.

Style with Seasonal Accessories

Jean shorts look so cute with boots! I’ve had these camel-colored riding boots for years and they go with everything in my closet. Another good season accessory to pair is a felt hat. I like to match so I made sure my boots and hat matched!

How to Wear your Favorite Denim Shorts into the Fall | Greta Hollar | How to Wear Denim Shorts by popular Nashville tall fashion blogger, Greta Hollar: image of Greta Hollar wearing a Farm Rio bodysuit, denim cut-off shorts, brown knee high boots, brown leather belt, and felt fedora hat.

Wear Tights Under Your Shorts

When it gets cold and you still want to wear your shorts, but some tights underneath! I’ve seen bloggers pair Gucci tights with their shorts or simple back tights and it looks so high fashion and chic.

Graphic Tee, Denim Jacket, and Booties

You’re not a true Nashvillian unless you pair your cut-offs with booties and a graphic tee shirt or crop top and denim jacket. It’s the perfect outfit for a day shopping in 12 South or Honky Tonking on Broadway!

How to Wear your Favorite Denim Shorts into the Fall | Greta Hollar | How to Wear Denim Shorts by popular Nashville tall fashion blogger, Greta Hollar: image of Greta Hollar wearing a Farm Rio bodysuit, denim cut-off shorts, brown knee high boots, brown leather belt, and felt fedora hat.

Oversized Cardigan

You can’t go wrong with a simple, plain tee and an oversized cardigan. It looks fall and festive while still being cool and having layers. You look cool, casual, and like a Madewell model in your fall outfits!

How to Wear your Favorite Denim Shorts into the Fall | Greta Hollar | How to Wear Denim Shorts by popular Nashville tall fashion blogger, Greta Hollar: image of Greta Hollar wearing a Farm Rio bodysuit, denim cut-off shorts, brown knee high boots, brown leather belt, and felt fedora hat.

Do you have any tips on how to style denim shorts? Share with me in a comment below. Also, if you’re tall like me, check out some of my favorite denim shorts for tall gals!

And always for style inspo, view my style board on Pinterest!

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Leave a Comment / Filled Under: ., Fall, Style, Summer

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greta  / nashvillian / content creator / traveler / dog mom / breast cancer fighter

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