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Winterize your wardrobe: 28 pieces for men (all under $50)

Give your wardrobe a revamp with half-zip sweaters, SAXX boxer shorts, a Henley shirt or the very popular Fruit of the Loom crew neck tee.
Peter Dazeley Getty Images white shirt
Revamp a fall wardrobe with easy-to-wear pieces.

If there’s more than one coming-apart-at-the-seams piece of clothing in your wardrobe rotation, a slight revamp for fall is in order. For this roundup of key pieces for men, we’ve kept all items under $50 and offered lots of variety for WFH (work from home) looks, durable stuff for those who work outside, and easy pieces for lounging.


Fruit of the Loom tees.

There’s no such thing as having too many white T-shirts (or grey, or black, or blue). These classic Fruit of the Loom crew neck shirts comes in a pack of four, with seven different colour options and sizes S-3XL. Available on Amazon.

Old Navy henley shirt.

Next up is a Henley, a casual staple that softens with wear and wash. First, choose a fit (slim fit, classic or big and tall) and find a colour that works on its own, or layer it under another shirt. Old Navy has a smart striped version (pictured) currently on sale for $12.

Amazon Basics half zip sweater.

Half-zip sweaters are everywhere right now because they are both comfortable and polished enough for the office — there are 18 different colours to choose from here, from basic grey to a punchy blue. Available on Amazon.  

Gap polo shirt

Want to step it up a little from a Henley shirt but don’t want to make the leap right to a button-down dress shirt? Polo shirts fall right in between, with a collar (a must for some office environments) and two buttons. You can tuck it into dress pants or wear it loose with jeans. The white is crisp and stylish and the taupe is very on-trend (but not too trendy) for 2021. Available at the Gap.

Old Navy gingham shirt.

To add a print to the mix, a gingham button-down is office-ready — wear it closed, layered with a Henley or under a vest. Available at Old Navy.

Old Navy roll neck sweater.

Roll-neck sweaters are just the right amount of preppy; this one comes in three colours (sage, grey and soft orange, pictured). Pairs well with khakis, jeans or tapered sweatpants. Available at Old Navy.

Amazon Basics hoodie.

Every closet needs a grab-and-go hoodie and this fleece sweatshirt is available in sizes XS-XXL and gets excellent reviews for comfort and softness. Available on Amazon.

Marks plaid shirt.

There’s no escaping a plaid shirt in Canada, so we’re embracing it with this classic from Mark’s. If the standard red/black check is a little too on the nose, the burgundy/black option (pictured) is a great colour combo. Available at Mark’s.

Gap pink shirt for men.

If basics are feeling a too predictable, step away from the black/white/grey/navy shades. Keep the cut classic (like this long-sleeve tee) and opt for some colour (like hot pink or bright blue) or a print, like green or purple tie dye. Available at the Gap.


Gap washwell jeans for men.

Gap’s Washwell jeans are a heavy denim with a bit stretch that wear well over time. These ones get high marks for comfort and shape. Available at the Gap

Joe Fresh corduroy pants for men.

If denim isn’t your go-to, these straight-leg pants are a grown-up take on cords. With a bit of spandex stretch, these are available in sizes 33x32-38x30. Available at Joe Fresh.

Old Navy twill pants for men.

These technically aren’t khaki pants, but the twill weave, colour and straight-leg cut are a khaki vibe (especially in the Doe A Deer shade); $17 (and limited sizes) at Old Navy.

Old Navy cargo pants for men.

Cargo pants are back in a big way (everybody needs pockets, right?). This pair modernizes the fit with a tapered ankle and slightly cropped fit. Available at Old Navy

Genuine Dickie pants.

Dickie’s is the go-to name in sturdy outdoor wear — Walmart has a selection of Genuine Dickies (made specifically for big-box retailers at a lower price point) like these work pants. Available at Walmart.

Joe Fresh sweatpants for men.

Coffee runs, WFH and lounging with friends are all reasons to slip into something a little more comfortable (we mean sweatpants, obviously). This pair has a subtle camo print, drawstring, pockets and a tapered leg. Available at Joe Fresh

Amazon double pack of sweatpants.

If you prefer your sweatpants in a more retro style, these have a wider fit and elastic ankle. Available on Amazon in a two-pack for double the comfort. 


Old Navy puffer vest for men.

Sometimes a chill in the air requires a little more than a long sleeve shirt but a little less than a coat — we’re pretty sure that’s why vests were invented. This puffer is ready to be layered over a new shirt. Available at Old Navy.

Quilted black jacket for men.

For a coat that works for the office as well as the weekends, this simple black quilted zip-up jacket is a nice change from anoraks. Available at Mark’s

Amazon Basics rain jacket.

That being said, there’s simply no escaping a rain coat here. If a name brand logo isn’t a concern, this no-fuss rain jacket with a detachable hood does the trick. Available on Amazon in four different colours (for slightly over $50).  


Adidas mens sneakers.

Sneakers should be worn until they fall apart (so comfort over trendy is the key). These Adidas NMD_R1 have the standard three-strip design in grey, with just a pop of orange and grey. (This is the only colour combo on sale for under $40.) Available at Sport Check.

Zoo York mens boots.

These Zoo York boots take notes from high-end designer lines with the all-black construction, rubber toe and shearling lining. They look a lot more expensive than the price tag ($42). Available at West49.

Mountain Warehouse hiking shoes.

For a mix of a boot and a sneaker, these ankle hiking boots work with sweats, jeans and cords. Comes in three different colour combos (we’re partial to the black/grey). On sale and selling fast at Mountain Warehouse.


Striped socks for men.

There’s no rule that socks need to be black or white. Mix it up with a striped pair, especially if pants show a flash of ankle. Available on Amazon

Thermal boot socks for men.

Double up on thick socks with this two-pack of moisture guard thermal boot socks. The blend of wool, copper, polyester, nylon and spandex wicks away moisture to keep feet dry and the arch support can help with long days in work boots. Available at Mark's

Carhartt toque for men.

Carhartt is a workwear brand that makes tough stuff, part of the reason we chose this toque. (The other part is that we like the ribbed look, colour options and design). Available on Amazon.

Insulated leather gloves.

Keep fingers protected with a pair of insulated gloves — these ones are lined with fleece on the inside and outside, the fingertips and palm are leather. Available at Mark’s.

SAXX boxer shorts.

If you are already a devotee of Vancouver underwear brand SAXX (or have been wanting to try out a pair,) go for the boxer shorts (currently on sale) or a popular boxer brief with a very unique print. Available at SAXX.

Thermal base layer set for  men.

This base set (long-sleeve shirt and compression long johns) is made for outdoor work (or skiing, hiking, jogging, etc.). The fabric is stretchy and wicks away moisture without adding any bulk. Available on Amazon.