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Men's Underwear

Sophisticated menswear with a touch of avant-garde, Le 31 appeals to the businessman, the innovator, the adventure-seeker, and the athlete with its wide range of collections that feature everything from the comfiest essentials to the season's trendiest pieces.

Editor's pick

Solid viscose trunk discounted price US$19.00
Le 31

New

Microfibre athletic boxer brief discounted price US$15.00
Le 31
Contrasting topstitch trunk discounted price US$15.00
Le 31
Feel tone-on-tone lyocell brief discounted price US$25.00
2 for $39.95
Le 31

Editor's pick

Solid viscose trunk discounted price US$19.00
Le 31

New

Striped band TENCEL™ modal boxer brief discounted price US$15.00
Le 31

New

Striped band TENCEL™ modal trunk discounted price US$15.00
Le 31

Editor's pick

Organic cotton ribbed tank regular price $35.00 discounted price US$24.95
Le 31
Mixed stripe viscose trunk regular price $20.00 discounted price US$14.99
Le 31
Organic cotton ribbed brief discounted price US$19.99
Le 31
Organic cotton ribbed legging regular price $40.00 discounted price US$24.95
Le 31
Striped grey trunk regular price $19.00 discounted price US$14.99
Le 31
Tone-on-tone Feel Lyocell boxer brief regular price $25.00 discounted price US$19.99
Le 31
Red stripe trunk regular price $19.00 discounted price US$14.99
Le 31
Red stripe brief regular price $19.00 discounted price US$14.99
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $35.00 discounted price US$24.95
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $35.00 discounted price US$24.95
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $35.00 discounted price US$24.95
Le 31
Tone-on-tone Feel Lyocell trunk regular price $25.00 discounted price US$19.99
Le 31
Organic cotton mesh brief discounted price US$19.99
Le 31
Organic cotton mesh trunk discounted price US$19.99
Le 31
Contrast-seam solid brief regular price $19.00 discounted price US$9.99
Le 31

Editor's pick

Twin-stripe brief regular price $19.00 discounted price US$9.99
Le 31
Jack & Jones at Simons

Founded in 1990 out of a love for denim, this European brand offers a complete range of clothing, underwear, and accessories for men.

New

Neon waist trunk discounted price US$15.00
3 for $34.95
Jack & Jones

New

Neon foliage trunk discounted price US$15.00
3 for $34.95
Jack & Jones

New

Green-and-blue trunk discounted price US$15.00
3 for $34.95
Jack & Jones

New

Vivid colour trunk discounted price US$15.00
3 for $34.95
Jack & Jones

Editor's pick

Large dot trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Orange-waist navy trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful band black trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Vibrant leaf trunk discounted price US$15.00
3 for $34.95
Jack & Jones

Editor's pick

Minimalist solid trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful skull trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Signature waist trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Surrealist illustration trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Monochrome trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Exotic jungle trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Lined waist blue trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Funky pattern trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Logo waist trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Tropical trunk discounted price US$15.00
3 for $34.95
Jack & Jones
PUMP! at Simons

Canadian Brand | This Montreal-based brand specializes in sports-inspired underwear made with meticulous attention to detail.

Switch micro-mesh cropped brief discounted price US$30.00
2 for $49.95
Pump!
Cruise trunk discounted price US$30.00
2 for $49.95
Pump!
Flash Jogger trunk discounted price US$35.00
2 for $49.95
Pump!
Velocity Touchdown trunk discounted price US$35.00
2 for $49.95
Pump!
Touchdown Ninja trunk discounted price US$35.00
2 for $49.95
Pump!
Sailor access trunk discounted price US$30.00
2 for $49.95
Pump!
Velocity jockstrap discounted price US$30.00
2 for $49.95
Pump!
Circuit jockstrap discounted price US$30.00
2 for $49.95
Pump!
NightLight jockstrap discounted price US$25.00
2 for $49.95
Pump!
Classic jockstrap discounted price US$25.00
2 for $49.95
Pump!
Switch mesh thong discounted price US$25.00
2 for $49.95
Pump!
Recharge micro-mesh thong discounted price US$30.00
2 for $49.95
Pump!
Classic jockstrap discounted price US$25.00
2 for $49.95
Pump!
Boost micro-mesh thong discounted price US$25.00
2 for $49.95
Pump!
Switch Access micro-mesh brief discounted price US$30.00
2 for $49.95
Pump!
NightLight trunk discounted price US$30.00
2 for $49.95
Pump!

For over 50 years, this American brand has fine-tuned its clean-cut, minimalist aesthetic by offering innovative pieces.

Classic microfibre trunks
3-pack
discounted price US$55.00
Calvin Klein
Classic microfibre boxer briefs
3-pack
discounted price US$55.00
Calvin Klein
Logo-waist shiny microfibre trunk regular price $25.00 discounted price US$14.99
Calvin Klein
Black Reconsidered Steel trunks
3-pack
regular price $69.00 discounted price US$39.95
Calvin Klein
Classic ribbed tanks
3-pack
discounted price US$50.00
Calvin Klein
Stretch microfibre trunks
5-pack
discounted price US$69.00
Calvin Klein
Classic stretch cotton trunks
3-pack
discounted price US$50.00
Calvin Klein
Colourful band pure cotton boxer briefs
5-pack
regular price $69.00 discounted price US$44.95
Calvin Klein
Classic stretch cotton boxer briefs
3-pack
discounted price US$50.00
Calvin Klein
Classic boxer briefs
3-pack
discounted price US$50.00
Calvin Klein
Cotton Stretch boxer briefs
3-pack
discounted price US$45.00
Calvin Klein
Microfiber Stretch boxer briefs
3-pack
regular price $50.00 discounted price US$29.95
Calvin Klein
Reconsidered Steel silver-waist boxer briefs
3-pack
discounted price US$60.00
Calvin Klein
Classic stretch cotton briefs
3-pack
discounted price US$50.00
Calvin Klein
Classic 100% cotton briefs
3-pack
discounted price US$45.00
Calvin Klein
Classic microfibre briefs
3-pack
discounted price US$55.00
Calvin Klein
Classic crew-neck T-shirts
3-pack
discounted price US$45.00
Calvin Klein
Classic V-neck T-shirts
3-pack
discounted price US$50.00
Calvin Klein

Canadian Brand | Founded in Vancouver in 2006, this underwear company looks to improve men's day-to-day with comfort technology that's tried and true.

New

Erik Abel sharks boxer brief
VIBE
discounted price US$30.00
Saxx

New

Hawaiian pizza boxer brief
ULTRA
discounted price US$30.00
Saxx

New

Sunset wave boxer brief
VIBE
discounted price US$30.00
Saxx

New

Camo coolers boxer brief
DAYTRIPPER
discounted price US$25.00
Saxx

New

Mini-stripe boxer brief
VIBE
discounted price US$30.00
Saxx
Hot sauce brief
DAYTRIPPER
regular price $25.00 discounted price US$14.99
Saxx
Face Melter boxer brief
DAYTRIPPER
discounted price US$25.00
Saxx
Logo waist black trunk
VIBE
discounted price US$30.00
Saxx
Solid light boxer brief
ULTRA
discounted price US$30.00
Saxx
Camping toast boxer brief
ULTRA
discounted price US$30.00
Saxx
Colourful illustration boxer brief
DAYTRIPPER
discounted price US$25.00
Saxx
Banana Split boxer brief
DROPTEMP™
regular price $30.00 discounted price US$24.95
Saxx
Solid boxer briefs
VIBE - 3-pack
discounted price US$79.00
Saxx
Gaming boxer brief
ULTRA
regular price $30.00 discounted price US$14.99
Saxx
Animal hockey player boxer brief
VIBE
regular price $30.00 discounted price US$14.99
Saxx
Season Pass boxer brief
DROPTEMP™
regular price $30.00 discounted price US$24.95
Saxx
Teal boxer brief
VIBE
discounted price US$30.00
Saxx
Office Party boxer brief
DAYTRIPPER
regular price $25.00 discounted price US$14.99
Saxx
Snowmobile yeti boxer brief
VIBE
regular price $30.00 discounted price US$24.95
Saxx
Hot dog boxer brief
VIBE
regular price $30.00 discounted price US$24.95
Saxx
Pixelated football boxer brief
ULTRA
regular price $30.00 discounted price US$24.95
Saxx

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!