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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.

TEES, SWEATERS AND BUTTON-DOWN SHIRTS

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

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

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 .  

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?  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 .

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

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 .

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

There’s no escaping a plaid shirt in Canada, so we’re embracing it with 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 .

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

DENIM, SLACKS AND SWEATPANTS

Gap’s 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 . 

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

These technically aren’t khaki 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 .

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 . 

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

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

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

VESTS AND COATS

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.  is ready to be layered over a new shirt. Available at .

For a coat that works for the office as well as the weekends, this simple black quilted  is a nice change from anoraks. Available at . 

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

SNEAKERS AND BOOTS

Sneakers should be worn until they fall apart (so comfort over trendy is the key). These 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 .

These 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 .

For a mix of a boot and a sneaker, these 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 .

UNDERWEAR, GLOVES AND TOQUES

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

Double up on thick socks with this two-pack of moisture guard thermal . 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 . 

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

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

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

This (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 .

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