21 Cute Ways to Wear High-Waisted Shorts

As you start to move your summer clothes out of your rotation and into storage, we have a style suggestion: Don't pack up your high-waisted shorts just yet. These shorts can work surprisingly well as transitional pieces and, when styled correctly, can be worn throughout fall and even into winter months.

That said, we're not suggesting you wear white linen shorts after Labor Day or shiver your way through your daily work commute in a pair of thigh-baring hot pants. One good rule of thumb is to consider high-waisted shorts an alternative to miniskirts when outfit planning. Another is to set aside any shorts in traditionally summery materials, but as with all things, there are exceptions to these style rules.

High-Waisted Shorts Styles

While there are loads of different high-waisted shorts styles, only a handful are transitional weather standouts. Pleated high-waisted shorts are a great choice for fall as they often appear in more heavyweight fabrics like wool and leather, in addition to cotton and linen. Denim is another top-notch autumnal textile and our reigning fave casual high-waisted shorts style. Last, but not least, paperbag high-waisted shorts are a great in-between-seasons secret weapon.

Because of their baggy fit, you can tuck in thicker tops like sweatshirts and cable knit sweaters without disrupting the lines of your look. If you plan to wear high-waisted shorts throughout the fall, we highly recommend taking advantage of summer clearance sales and getting yourself a pair of paperbag shorts so you can tuck in even the chunkiest of sweaters without feeling cinched or squeezed.

How to Style High-Waisted Shorts

Wearing high-waisted shorts in cool or chilly temps is all about layering, but that doesn't mean you have to abandon your summer go-to styling techniques. Crop tops and bralettes are still fair game, but we recommend adding a blazer or cardigan layer, plus a jacket on top. Long-sleeved tops are a foolproof option, but short-sleeved tops can work, especially when worn under a tucked-in sweater.

To give the illusion of fewer layers, try a long-sleeve thermal (fully tucked in) paired with a half-tucked button-down shirt. Worried about all these layers looking bulky around your waist? Don't fret. Just add a statement belt to redirect the eye and you'll be good to go.

With these styling types and shorts styles in mind, you'll have no trouble making these 21 high-waisted shorts ideas work for you all season long.

David Miller

David Miller

Executive Financial & Market Analyst

David Miller brings 15 years of experience in global economics, personal finance strategy, and market dynamics. He specializes in turning complex economic trends into actionable insights for everyday readers.