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Men's Underwear

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Featured

New

Playful print loose boxer brief discounted price US$19.00
Djab

New

Playful print loose boxer brief discounted price US$19.00
Djab

New

Playful print loose boxer brief discounted price US$19.00
Djab

3 for $34.95

Contrasting topstitch trunk discounted price US$15.00
3 for $34.95
Le 31
Contrasting topstitch trunk discounted price US$15.00
3 for $34.95
Le 31
Contrasting topstitch trunk discounted price US$15.00
3 for $34.95
Le 31
Bright organic cotton trunk discounted price US$19.00
3 for $34.95
Le 31
Bright organic cotton trunk discounted price US$19.00
3 for $34.95
Le 31
Bright organic cotton trunk discounted price US$19.00
3 for $34.95
Le 31

Most popular trunks

+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
Retro stripe trunk discounted price US$20.00
Le 31
Tone-on-tone Feel Lyocell trunk discounted price US$25.00
Le 31
Tone-on-tone Feel Lyocell trunk discounted price US$25.00
Le 31
Contrast-line modal trunk regular price $19.00 discounted price US$14.99
Le 31
Contrast-line modal trunk regular price $19.00 discounted price US$14.99
Le 31
Contrast-line modal trunk regular price $19.00 discounted price US$14.99
Le 31

Most popular boxer briefs

Grillicious boxer brief
VIBE
discounted price US$30.00
Saxx
Nautical stripe boxer brief
VIBE
discounted price US$30.00
Saxx

Editor's pick

Woodland camo boxer brief
VIBE
discounted price US$30.00
Saxx
Earthy boxer brief
VIBE
discounted price US$30.00
Saxx

New

Midnight Tropics boxer brief
VIBE
discounted price US$30.00
Saxx
Mini-stripe boxer brief
VIBE
discounted price US$30.00
Saxx

Most popular briefs

Tone-on-tone Feel lyocell brief discounted price US$25.00
Le 31
Tone-on-tone Feel lyocell brief discounted price US$25.00
Le 31
Tone-on-tone Feel lyocell brief discounted price US$25.00
Le 31

New

Contrast-seam solid brief discounted price US$19.00
Le 31

New

Contrast-seam solid brief discounted price US$19.00
Le 31

New

Contrast-seam solid brief discounted price US$19.00
Le 31

Most popular multi-packs

Solid organic cotton boxer briefs
2-pack
discounted price US$19.99
Le 31
Classic organic cotton boxer briefs
2-pack
discounted price US$19.99
Le 31
Classic stretch cotton boxer briefs
3-pack
discounted price US$50.00
Calvin Klein
Classic microfibre trunks
3-pack
discounted price US$55.00
Calvin Klein

New

Solid microfibre trunks
3-pack
discounted price US$50.00
Calvin Klein
Classic stretch cotton trunks
3-pack
discounted price US$50.00
Calvin Klein

Most popular boxers

New

Organic cotton flannel loose trunk discounted price US$25.00
Le 31
Loose organic cotton jersey boxer regular price $19.00 discounted price US$14.99
Le 31

New

Organic cotton flannel loose trunk discounted price US$25.00
Le 31

Most popular tanks & T-shirts

Organic cotton V-neck lounge T-shirt
2-pack
discounted price US$24.95
Le 31
Classic ribbed tanks
3-pack
discounted price US$50.00
Calvin Klein
Classic crew-neck T-shirts
3-pack
discounted price US$50.00
Calvin Klein

Trunks

New

Solid viscose trunk discounted price US$19.00
Le 31
Foliage trunk regular price $19.00 discounted price US$14.99
Le 31
Colourful snack trunk regular price $19.00 discounted price US$14.99
Le 31
Sports club trunk regular price $19.00 discounted price US$14.99
Le 31
Denim-like trunk regular price $19.00 discounted price US$12.99
Le 31

Editor's pick

Bright microfibre trunk regular price $15.00 discounted price US$9.99
Le 31
Colour block trunk regular price $19.00 discounted price US$14.99
Le 31
Colour block trunk regular price $19.00 discounted price US$14.99
Le 31
Nautical stripe trunk discounted price US$19.00
3 for $39.95
Le 31
Hatched stripe trunk discounted price US$19.00
3 for $39.95
Le 31
Burgundy stripe trunk discounted price US$19.00
3 for $39.95
Le 31
Heather grey trunk discounted price US$19.00
3 for $39.95
Le 31
Vertical blue stripe trunk discounted price US$19.00
3 for $39.95
Le 31
Geometric shape trunk discounted price US$19.00
3 for $39.95
Le 31
Festive print trunk discounted price US$19.00
Le 31

Editor's pick

Colourful bamboo rayon trunk discounted price US$15.00
Le 31
Recycled micro nylon trunk discounted price US$19.00
Le 31
Sports club trunk discounted price US$19.00
Le 31

New

Saturated foliage trunk discounted price US$15.00
Jack & Jones

New

Saturated foliage trunk discounted price US$15.00
Jack & Jones

New

Funky camo trunk discounted price US$15.00
Jack & Jones

New

Funky camo trunk discounted price US$15.00
Jack & Jones

New

Contrast foliage trunk discounted price US$15.00
Jack & Jones

New

Contrast foliage trunk discounted price US$15.00
Jack & Jones
Two-tone band trunk discounted price US$15.00
Jack & Jones
Two-tone band trunk discounted price US$15.00
Jack & Jones
Two-tone band trunk discounted price US$15.00
Jack & Jones
Graffiti globe trunk discounted price US$15.00
Jack & Jones
Yellow graffiti trunk discounted price US$15.00
Jack & Jones
Vivid colours trunk discounted price US$15.00
Jack & Jones
Vivid colours trunk discounted price US$15.00
Jack & Jones
Monochrome microfibre trunk discounted price US$15.00
Jack & Jones
Tropical hue trunk discounted price US$15.00
Jack & Jones
Dotted hatched logo trunk discounted price US$15.00
Jack & Jones
Logo waist trunk discounted price US$15.00
Jack & Jones
Logo belt trunk discounted price US$15.00
Jack & Jones
Signature waist trunk discounted price US$15.00
Jack & Jones
Beer Pong trunk
VIBE
discounted price US$30.00
Saxx
Logo waist solid trunk
VIBE
discounted price US$30.00
Saxx
TENCEL* Lyocell solid trunk regular price $35.00 discounted price US$14.99
Organic Basics

Editor's pick

Slim fit trunk discounted price US$30.00
JM

Editor's pick

Slim fit trunk discounted price US$30.00
JM
Second skin trunk discounted price US$25.00
JM
Solid pop-coloured trunk regular price $25.00 discounted price US$19.99
Calvin Klein
Solid pop-coloured trunk regular price $25.00 discounted price US$19.99
Calvin Klein
Solid pop-coloured trunk regular price $25.00 discounted price US$19.99
Calvin Klein
Solid pop-coloured trunk regular price $25.00 discounted price US$19.99
Calvin Klein
Tropical pattern double trunk discounted price US$45.00
Diesel
Red detail trunk regular price $35.00 discounted price US$24.95
Diesel

New

Abstract camo trunk discounted price US$45.00
BOSS
Blue repeat-logo trunk regular price $35.00 discounted price US$19.99
BOSS
Blue scale trunk discounted price US$45.00
BOSS
Trimmed logo trunk discounted price US$35.00
BOSS
Mint green logo trunk regular price $35.00 discounted price US$19.99
BOSS

New

Geo print trunk discounted price US$35.00
BOSS

New

Flecked green trunk discounted price US$45.00
BOSS

New

Monogram trunk discounted price US$35.00
BOSS

Men's Boxers & Briefs

Whether you're working, training at the gym, or simply relaxing at home, comfort is a priority. And when it comes to comfort, choosing the right underwear is key. At Simons, we offer a wide variety of trunks, boxers, and boxer briefs to suit your every need.

 

Take your pick in our selection of high-quality, comfortable, and sometimes playful designs by Calvin Klein, Jack & Jones, BOSS by HUGO BOSS, SAXX, or our private brand, Le 31. Make sure to choose the fabric that's right for you. Your underwear should be stretchy and breathable. Cotton, modal, and bamboo rayon are particularly popular!