Men's Tailored Swim Shorts | Tom & Teddy

Tailored Trunks


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Tailored Trunks


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Our new tailored swim shorts have a smooth waistband and secure snap fastening, plus a little give at the sides for an easy, versatile style that’s never too tight but looks and feels smart and stylish. Plus, we think you’ll agree that we’ve hit the sweet spot with the length – a more tailored trunk needs a slightly shorter than mid-thigh hemline to keep things cool and contemporary! Browse the collection and add a pair of super-soft, quick-dry, feel-great Tailored trunks to your 2020 sunny-weather wardrobe.

View our tailored swim shorts

The Perfect Fit

The Tailored Trunks are the perfect-fit, ultra-flattering, wear-everywhere shorts that you can swim in! The soft, quick-dry fabric feels great against the skin, so you’ll want to wear them all day long, in or out of the water. This style of Tom & Teddy shorts features:

  • Zip fly
  • Snap fastening
  • Smooth inner drawcord
  • Side pockets
  • Back pocket with zip closure
  • Partially elasticated waistband
  • Soft mesh inner brief

Match up your Tailored Trunks with a pair of Classic Trunks for the little guy. Each of the Tailored Trunks prints are also available in the boys’ elasticated-waist style.
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Find Your Perfect Trunks

Follow our quick guide to choosing a pair of trunks that are flattering, but also feel great as you swim some laps in the pool, dive under waves or take a run along the sand. All our super-soft and quick-dry trunks are designed to be worn all day long, either in out or out of the water.

  • The fit

    Classic Trunks

    Our original elasticated-waist swim shorts with a tough draw cord, so you can adjust the fit and wear them at the waist or lower towards the hips if preferred. They have a straight, semi-tailored leg with plenty of room in the width, making them ideal for water sports, running or active play with the kids.

    Tailored Trunks

    Our updated tailored style is our shorter, smarter swim short to take you to the beach and beyond. These trunks have a flat-fronted waistband with a zip-fly and secure snap fastening, and incorporate elasticated sections at the sides for extra versality and comfort. They are slimmer in the leg than our Classic Trunks.


    Voluminous swim shorts that flap around the knees may not be flattering. A mid-thigh or above-the-knee short is easy and comfortable with just the right amount of coverage for beach, pool or bar. Combining this length with a straight or slim cut will give you a smart, put together look, rather than a beach-bum vibe. Our Classic Trunks sit at the lower-to mid-thigh point and the Tailored Trunks are designed to finish a little higher on the thigh (mid-thigh or above) to balance with the slimmer leg.


    You might love a zesty yellow pair of swim shorts, but will they love you back? Make sure you start your swim-trunk selection process by assessing your skin tone and choosing shorts in shades that will complement it, not wash it out. As a rule, bright colors look better on darker complexions and classic shades are flattering on fairer skins.


    Swimwear prints and patterns are bolder and brighter than ever before. Why? Because in sunny climates and holiday locations, strong shades and fun designs look fantastic. If you’re usually quite a conservative dresser, take the opportunity to try a lively printed pair of trunks. It’s tempting to revert to your usual solid color or nautical stripes but, we promise, something a little more unusual looks super stylish and appropriate at the beach.