How to Wear Shorts During Fall, According to 20 Fashion Bloggers

Kristen Bousquet
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STYLECASTER | How to Wear Shorts in Fall/Winter | Outfit Ideas
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Photo: Getty Images

The quintessential model-off-duty look, shorts during cold weather may not seem to make a ton of sense, but we do it anyway. You know, for fashion.

Especially considering the fact that some of the best sales on summer staples like shorts happen in late August and early September, it only makes sense that we want to buy them and immediately put them to use. Plus, when styled well, shorts during fall and winter look totally seasonally appropriate, so definitely don’t pack yours away after Labor Day because you’ll be missing out.

MORE: 9 Fall Beauty Finds to Nail the Seasonal Transition

And don’t worry, there are ways to wear shorts during cold weather that will keep you warm, comfortable, and impossibly chic. Paired with chunky sweaters, blazers, over-the-knee boots, and tights, shorts can be a staple during any season.

Get inspired by the street style looks ahead and get ready to break out your favorite pair of shorts on the next cool fall day.

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STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Pair With a Cozy Sweater
Photo: Dulceida
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Over-the-Knee Boots
Photo: Brunette Braid
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Overalls Are In
Photo: Fashion Agony
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Canadian Tuxedo
Photo: Venka Vision
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Sheer Tights
Photo: Andy Sparkles
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Combat Boots
Photo: The Sense
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Bold Denim
Photo: Street Style Seconds
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
All Leather
Photo: Ohh Couture
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Spunky Patterns
Photo: Closet Candy
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Cool and Casual
Photo: The Fashion Cuisine
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Barely There
Photo: Hapa Time
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
High Waisted
Photo: Someone Like You
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Almost a Skirt
Photo: Kolorowa Dusza
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Half Tucked
Photo: Skinny Budha
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Statement Scarf
Photo: Red Reiding Hood
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Tiny Polka Dots
Photo: A Clothes Horse
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Cutoffs
Photo: Style Du Monde
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Black on Black
Photo: Le Blog de Betty
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Animal Print
Photo: Styling My Life
STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
Cropped Turtleneck
Photo: Stockholm Streetstyle

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  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas
  • STYLECASTER | How to Wear Shorts During Fall & Winter | Fall Outfit Ideas

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