4 Versatile Ways To Wear Plaid Shirts

by Jamie Wilson
What is an Overshirt

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

A must-have piece for any well-rounded wardrobe, follow these simple tips to rock plaid in any situation.

It’s technically winter for another two months, and realistically it’ll be at least another month after that, before anyone can say spring has sprung. Just because the sun is tucked away doesn’t mean you need to be, though, and a quality plaid shirt is just the trick to keep your sartorial skies clear.

Typically a heavier fabric with a tartan check, plaid is a practical and stylish option that can be dressed up or down to fit any occasion this season. It can also take you through the whole year and more. Here are four ways to wear your plaid shirt.

So Laid Back It’s Horizontal

A plaid shirt is autumnal styling, that’ll never go out of fashion. Layer with a tee and jacket on those chilly year-end mornings, to keep you feeling warm and looking hot. A rough-and-tumble fabric, pair plaid with hard-wearing partners; thick cotton tees, rough denim, and rugged leather are the order of the day.

Perfect for popping to the shops or the morning-after-the-night-before greasy fry-up, you can throw this on in five minutes and look like you took much longer. Easy wearing at its best.

For casual style with a bit more meat, wear jeans and your plaid shirt with a beanie and workboots. Throw in a pair of fingerless gloves, and really feel that blue-collar funk.

If you’re feeling a bit more catwalk than high street, try layering heavy plaid over another, lighter, shirt, or pairing one plaid shirt with another wrapped around the waist – though for gods’ sakes, make sure they compliment, or this outfit won’t say anything good about you.

Nights Out In Style

Plaid adds character to that shirt-and-jeans combo, that’s a favourite of Friday night pints – tuck it into jeans or cotton trousers and bang! Just like that you’ve gone from “lads on tour” to “man about town”.

This is a style where less is more; matched shoes, belt, and watch, are all it takes to make sure you catch every eye in the room. However, this also means each individual piece has to pull its own weight, and an ill-fitting shirt just won’t cut it.

Look for a fit that avoids billowing, without edging into stuffed-sausage territory, and shoulder seams that stop over your shoulder bones. You’ll want cuffs that move easily over your watch, and sit in the crook between wrist and thumb, and a collar you can still run a finger ‘round once buttoned.

It’s a comfortable and self-assured combo that looks good without trying too hard, but if this is a little too generic, then friend, are you ever in luck. Plaid was made for expressing individuality: banned in the 1700s as part of a move to crush Scottish independence before then being appropriated by Victorian gentility, swapping your belt for braces harkens back to the 70s, when it was finally reclaimed by a vibrant – and sometimes violent – counter-culture.

The skinhead look is iconic, and makes a hell of a statement, but has become pretty heavily stigmatised, so be careful that it’s a statement you want to make. A bomber jacket is a necessity if you want to go all-in on this 70s style, but be aware that overcommitting, may undermine the smarter vibe we’re going for here.

Meeting The Mates

You’ve been seeing your special someone for a while now, and against all better judgement, they’ve decided they want you to meet their friends. You want to make the right impression: smart, but not stick-up-your-ass formal; easy-going, but not slobby. Where do you turn? Where do you think?

A solid pullover, with a bit of cheeky plaid cuff n’ collar action, says mature without mundane. Less meeting the parents, more meeting the mates, this is the sort of look that’ll launch you straight into your partner’s good books.

Take the chance to bust out some of the more garish plaids around, by pairing your shirt with something in a neutral tone – like this sweet textured number – to tamp down on the shock factor and ensure you’re turning heads for the right reasons.

A bit more “country pub” than “wild in the club”, I like this look paired with mulled cider and a wood fire, personally. If you’re digging the pastoral styling but want something with a bit more energy, try a quilted vest or windbreaker with hiking boots for a more rugged take on this look.

Smarter-Than-Einstein Smart

If, on the other hand, you want to go even smarter – I’m talking University Challenge-levels of smart – plaid has got you covered. What did you expect? It’s a menswear miracle. Mix it up with a vest or blazer and your shirt will be at home in any situation, from inner-city power-lunches to cocktails in the evening.

Throw a solid knitted tie into the mix, or a matching pocket square, and strut around the office like it’s Milan up in here. Dress for the job you want they say, and this number will have your manager sweating buckets.

Need an excuse to wear tweed? You don’t, but you’ve got one here anyway. If you’ve invested in a grey flannel suit, then you shouldn’t need me to tell you how to add two and two.

A Word of Warning

Plaid is amazing stuff, but some fashion gaffs just can’t be salvaged. As with any shirt, fit is always more important than pricetag – after all, an £100 shirt won’t do you any favours sat in your wardrobe.

Plaid was made to pair, but be careful about mixing it with other patterns and contrasting colours – or run the risk of looking like something the dog produced after eating a box of crayons. If your shirt features a particularly bold pattern, mix it with neutral tones to keep it classy. If, on the other hand, you’ve opted for a more muted outfit, then throwing a little contrast into the mix can bring your whole outfit to life.  

The key to building a wardrobe, is finding versatile pieces. An autumn essential for a reason, a sweet plaid shirt will do serious work for you. Wear it open and layered, for a go-to casual option, or as a stand-alone piece with smart shoes and jeans, for an eye-catching option on Friday nights.

Combo with a pullover, to take your plaid shirt from casual to respectable – without edging into fussy – or don a vest or blazer for office-wear with edge. Wear it right, and not only will your plaid shirt look right at home in a whole spectrum of social situations, but so will you.

Feature image from Pinterest

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