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  1. GERRY BOARDIE GERRY BOARDIE Sale
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  2. AFRICAN CAMO BOARDIE AFRICAN CAMO BOARDIE Sale
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  3. KRAVAT SWIM SHORT KRAVAT SWIM SHORT Sale
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  4. AFRICAN GEO SWIM SHORT AFRICAN GEO SWIM SHORT Sale
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  5. ZAZU BOARDIE ZAZU BOARDIE Sale
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  6. GERRY BOARDIE GERRY BOARDIE Sale
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  7. OM KNIT SHORT OM KNIT SHORT Sale
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  8. TIE DYE SWIM SHORT TIE DYE SWIM SHORT Sale
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  9. ULTRA RUN SHORT ULTRA RUN SHORT Sale
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  10. ULTRA RUN SHORT ULTRA RUN SHORT Sale
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  11. ULTRA TRAINER SHORT ULTRA TRAINER SHORT Sale
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  12. ULTRA TRAINER SHORT ULTRA TRAINER SHORT Sale
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12 Items

per page
Set Descending Direction

If you're looking for shorts that work as hard as you do, then look to THE UPSIDE. Not only do our shorts help you look your best, but our they can also help you feel your best. It’s all thanks to their equally practical and stylish design. We use classic colours as well as inspired patterns to create looks and fits for everyone.

Unlike other men’s gym shorts and swim shorts that can ride up or drag down, our pieces are made to stay in firmly place. They are fitted enough to provide a structured, clean look, but roomy enough to allow for movement and comfort. The result is our collection of sleek short designs that adapt to your body's movement and offer optimal measures of ease and support.

Our lineup of performance shorts are made from soft, strong and flexible and breathable fabric that can withstand your most intense sweat session, leaving you dry and chafe-free. Our swim shorts offer inner support, quick dry performance fabric, as well as beach-ready style. All of our shorts feature a flattering wide-elastic waist that is not only comfortable to wear, but keeps your shorts firmly in place. What’s more, our shorts aren’t too long or baggy, so you’ll look trim and put-together.

Another thing to love about our shorts? They're the right length. While these swim and men’s gym shorts definitely fall under the category of casual wear, they have still been designed for the consummate gentleman. This means short-shorts are out, as are long and awkward styles. All our shorts fall at our a few inches above the knee, offering the most flattering cut for any guy - and that’s what all great fashion does: it looks great on anyone.

THE UPSIDE doesn’t create men’s gym and swim shorts for a specific looking person. We create a range of shorts for people looking for specific qualities in their activewear: functional wearability and classic style. This doesn’t mean tired, old style. Our fabrics and patterns are undeniably on-trend, and our cuts and fits are on-point with what men really want to wear.