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A Gentleman's Guide to Socks and Underwear

By: Sharp Staff|November 12, 2014



Bjorn Borg

Short shorts solid, $25

This Swedish underwear brand knows what’s important: mesh inserts provide additional ventilation and anti-chafing flatlock stitching make sure every move is comfortable.

Derek Rose

Tennis Pina cotton stretch hipster, $45

Inspired by Wimbledon, these tennis-printed shorts are cut from fine gauge Pima cotton, with a hint of stretch. The retro striped waistband is reminiscent of retro headbands seen on the court. Never doubt your sports prowess again.


Sasha, $35

When a product is ‘Made in Canada’ you know it’s going to be good. Made from rayon from bamboo and a bit of spandex, these shorts have a super soft silky-cashmere feel and easy breathability. Damn, that’s good bamboo.


The Hill-side, $20

Wearing droopy socks is almost as bad as wearing damp ones. These Hill-side ribbed crew socks are made with a double-layer cuff preventing them from falling down. And they’re just as cozy as they come.


Blind Bag, $20

Don’t count on buying Huely socks to perfectly match your suit. The socks you order remain a complete mystery until you open the ‘blind bag’ they come in. Every pair is different and designed by a different artist of brand creator Nate Kogan’s choosing.

My Pakage

Weekday, $25

The lightweight ‘weekday’ shorts from My Pakage offers ultra breathable support and comfort perfect for sitting at a desk all day. Weekends deserve their ‘weekend’ shorts made with heavier and more durable fabric for rowdier activities.

The Naked Shop

Silver boxer brief, $40

The Naked Shop deems these shorts as the ‘underwear that can be worn for longer than it should.’ Made from thread that has been bonded with 99% pure silver, which naturally inhibits the growth of odor-causing bacteria, plus thermodynamic properties, these shorts will keep you cool in the summer and warm in the winter.

Saxx Underwear

Platinum boxer fly, $35

To achieve the light softness of these shorts, Saxx Underwear blends Modal (a natural fibre made from a European beachwood pulp) and spandex.

Socking Behaviour

Subzero striped bugatchie mens socks, $25

Easily paired with dress shoes or stylish sneakers, these socks are made in Italy from extremely durable mercerized cotton.


Allen Iverson socks, $15

Express your love for everything from NBA teams to individual players and original artwork to the oceanside. All on your feet! It doesn’t get any easier than that.


Wool socks in turmeric, $40

These socks are made of a raw wool blend (dyed with natural turmeric) to keep you as warm as possible in low temperatures.

Yo Sox

Wham Bam, $10

This Toronto based designer sock brand specializes in colorfully patterned and novelty designs. They’re perfect for a pair of feet with a sense of humour. Made from compact cotton, the makers ensure that you’re not sacrificing comfort for design.


Emporio Armani

Boxers, $40

Armani has been making flawless mens underwear for decades and these cotton jersey shorts continue the tradition.

H&M’s David Beckham

DB three-pack boxer shorts, $35

We’re not saying that having his own brand of underwear is what makes David Beckham so awesome…but we’re also not not saying it. Made with mostly cotton and a bit of spandex, these shorts are as comfy as it gets. How else would he bend it like Beckham?


Two tone geometric pattern socks, $8

Since Tristan also specializes in menswear, they know how to make a sock that will look good against almost any kind of suit. Made from combed cotton.


Padded sports socks, $14

These socks from Lululemon are runner’s socks. The breathable Mesh inserts and wicking nylon yarns help keep your feet cool and dry despite your sweat level. A ‘Y’ heel helps keep your socks from slipping into your shoes.

We did some homework to find the brands whose products won’t droop after only a few wears.

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