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How To Wear Long Shorts

How To Wear Long Shorts

Building your uniform with a practical summer classic.

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Ali Pew
Jul 11, 2025
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How To Wear Long Shorts
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Shorts with a long hemline have been a core part of my summer wardrobe for many years. They are practical, sometimes you just don’t want to sit on bare legs, and a cool modern take on summer dressing. I like the boyish look and juxtaposing with a feminine top or styling nod. They can be polished enough for an office (similar to a trouser) or casual for a vacation (cotton and drawstrings). The trick to making the longer length feel cool is in the styling.

A few images above of how I’ve worn over the years including an old Jil Sander pair with an oversized waist tie (some good similar options below), paired with my summer favorite lemon yellow, and with my favorite “where anywhere” gathered top from Toteme (top center).

Here are four of my latest long shorts and how I’m styling them.

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