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Men’s Plaid Pants Outfit Inspiration: 13 Ways To Wear Them In 2024

Men shy away from checked/plaid pants, but they're easier to wear than you think. Here's how to make a statement without trying too hard.

Words by: Charlie Thomas

Most of the time, trousers are an afterthought. In menswear, it’s the top half of our outfits that tend to get the attention while even our go-to pant styles, like jeans and chinos, sit quietly down below, almost as though they were designed not to be noticed. This is not the case with plaid pants.

A legwear style that well and truly demands attention, check patterns literally draw the eye down, making your bottom half the focal point. Plaid pants are bold, but if you want to make a statement or you’re stuck in a wardrobe rut, they can be the perfect way to make you stand out.

Just make sure you do so for the right reasons. You don’t want to look like a 70s golfer, or like you’re wearing a pair of festive PJs. To help you whittle down the best patterns and find the right fit, we’ve squared off everything you need to know, including some modern plaid pants outfits that won’t have you looking like a children’s TV presenter.

How to wear plaid pants: what to consider

The type of check

Men's close up of checked pants pocket

Ralph Lauren

Plaid pants come in many forms, from simple overcheck patterns, consisting of a single colour, to complicated multi-check patterns like Prince of Wales or blue and green Black Watch. There are high-contrast houndstooth styles and sober windowpane options. So which one to go for?

Check trousers can essentially be as out-there as you want, but unless you’re channelling the punk scene with some bold tartan, we’d recommend subtle checks with a couple of complementary colours for maximum wearability.

The colour palette

Selection of men's checked/plaid pants on a table

Todd Snyder

Colour is integral to plaid fabrics. The simplest checks boast only one or two colours, but louder styles can have multiple shades woven into them. Scottish tweeds and tartans for example can easily have up to seven or eight colours in them ranging from red and orange to blue, green and yellow.

Of course, wearing bright red tartan trousers is not for the average mild-mannered menswear connoisseur. Unless you’re going to a Scottish country show, start by deciding on a rough colour palette and take it from there. A good place to begin is with tonal plaids, like navy checked with shades of lighter blue.

The fit

Men's pleated plaid/checked pants with tucked in knitted polo shirt

Todd Snyder

Plaid pants tend to work better with smarter attire. Depending on the exact check, they fall on the more formal end of the spectrum, and are more regularly available in dress trouser form, including pleated designs or high-waisted suit trousers. So for those seeking plaid pants to work with tailoring, it’s best to stick to a more streamlined, slim fit.

Look for a cut that has some room in the thigh but tapers down to the ankle, resulting in a narrow hem that sits just about your shoes. Go for a pair that’s too skinny and it’ll warp the check pattern, making it look stretched and just plain wrong. You want the trousers to hang naturally so the check sits straight.

For something more relaxed, a pair of wider leg plaid pants aren’t a bad option. Incorporate them into streetwear-inspired looks by sticking with subtle grey patterns, which combine quite easily with logos and vibrant colours and won’t clash too heavily with sneakers.

Plaid pants outfits

Dressed down plaid pants

Men's grey checked pants, beige crew neck sweater and white sneakers outfit


Plaid pants are naturally at home when dressed up with tailoring, but it’s more than possible to make them work in a casual fit. Take a grey pair and match them up with a stone crew-neck jumper and leather sneakers and you’ve got a look that works for casual Friday in the office or out on the town in the evening.

Pleated plaid pants

Men's pleated plaid pants, camel roll neck, cream overcoat and suede Chelsea boots outfit

Moss Bros.

For all-out tailored luxury, a pair of pleated check trousers are hard to beat. Go for some with a grey base and a subtle two-line check and you can wear them with navy blazers, black overcoats or softer shades like stone and ecru.

Try a cream roll neck, stone topcoat and suede Chelsea boots – it’s a smart look that’ll easily make you the sharpest in the office.

Streetwear-inspired plaid pants

Men's grey checked pants, logo sweatshirt and black high-tops streetwear outfit


While they do accompany tailored looks more naturally, plaid pants can be worn as part of a streetwear get up if you lean into their punk or skatewear heritage.

The trick is to keep things minimal down below: go for a tonal check trouser in light grey and combine them with canvas high-tops and a logo sweatshirt in black for an alternative take on off-duty dressing.

Plaid pants and denim

Men's plaid pants, roll neck and raw denim jacket outfit

As is usually the case, a denim jacket is capable of dressing down whatever you wear with them. Plaid pants are no exception – it keeps them from looking too stuffy or over the top.

Go for a raw denim version and Prince of Wales check trousers for an interesting high/low play, and complete the look with a charcoal roll neck and chunky Derbies.

Plaid pants and Chelsea boots

Men's dark checked trousers, brown leather chelsea boots, white roll neck and suede aviator jacket outfit


Chelsea boots are one of those perfect in between shoes – not too smart but not too laid back either. They’re a good match for plaid pants then, as they offer a little sharpness without taking things into boardroom territory.

Try wearing your Chelsea boots with navy checked trousers, a turtleneck and suede aviator jacket.

With a hoodie

Men's small check pants, white hoodie and boat shoes preppy streetwearoutfit


In an interesting mix of smart and relaxed, try combining an off-white hoodie with some grey multi-check trousers and a pair of suede boat shoes. The laid-back associations of the hoodie instantly bring the trousers down a peg or two, while the boat shoes tip the outfit into the modern-day preppy aesthetic which is so on trend.

Keep it simple

Men's plaid pants, mustard T-shirt and sneakers outfit

Hugo Boss

As mentioned, wear plaid pants and chances are they instantly become the first thing anyone will notice. Which is why it’s best to keep everything else simple. Try some overcheck trousers with a short sleeve tee and minimal sneakers and you can’t really mess it up.

Just make sure the fit is on point and the trousers aren’t too slim.

Vintage-inspired plaid pants

Men's grey plaid pants, brown T-shirt, suede jacket and brown Derby shoes outfit

Pal Zileri

Certain plaid pants have a very 70s feel to them, because the style was immensely popular during this adventurously-dressed decade.

Channel a bit of throwback action and go for a grey multi-check pair, combining them with a brown T-shirt, suede jacket and brown leather Derbies, finished without socks for a more contemporary twist.

Plaid pants and wardrobe staples

Men's Black Watch tartan pants, white roll neck, denim shirt and white sneakers outfit


Just because you’ve bought a pair of plaid pants doesn’t mean you have to reinvent your entire wardrobe. If you purchased a Black Watch tartan pair, for example, they can easily be worn with common wardrobe staples including denim or chambray shirts, turtlenecks and minimal sneakers, as proven above.

Plaid pants with a turtleneck

Men's smart plaid pants, burgundy turtleneck and brown leather boots outfit


When fall and winter roll around, a turtleneck should be high on your list of wardrobe priorities. Find one in a seasonally-appropriate deep red tone and wear it with some subtly checked grey/brown tailored trousers and leather Derbies.

It’s a simple look but one that packs plenty of punch – you won’t get lost in a suit of blue and grey suits, that’s for sure.

Formal plaid pants

Men's plaid pants, blue Oxford shirt, navy double breasted blazer and suede shoes outfit


For a failsafe separates combination, pair a blue double-breasted blazer with grey check pants and a denim shirt – the colour palette is simple, allowing each piece to work in unison.

Finish with suede Oxford shoes for a smart flourish that makes this look appropriate for office wear, weddings and more.

Plaid pants anchored with white sneakers

Men's dark checked trousers, white T-shirt and padded field jacket outfit


Minimal white sneakers are perfect for dressing down looks, keeping them from getting too smart, colourful or loud. In short, they’re ideal for combining with plaid pants, especially those that are on the modest side of things.

Try a simple pair of leather kicks with a blue and white chalk-stripe check, and finish with a white T-shirt and down jacket for added warmth.

Complementary top & bottom half

Men's checked cuffed pants, knitted sweater and green parka jacket worn with high-top sneakers outfit


One way to approach wearing plaid pants is by coordinating your colours. If, for example, you’re going for a green and grey patterned pair, try mirroring that in the top half of your look, with grey knitwear and a green parka. Complete the affair with some canvas slip-ons, which keeps things from getting too out-there.