How to Wear a Polo Shirt With Style

The polo shirt gets a bad rap. It’s one of those men’s wardrobe items that’s often undervalued, used only for backup. It’s a necessity, something that’s there when you don’t have anything to wear, or when you know you’ll have to take your shirt off. It’s a breather in an outfit, a rest stop, an intermission. Keeping me, it feels like, from going too far, taking myself too seriously. But it’s actually one of the most versatile things you can have in a menswear collection. Sandwiched between a tee and a dress shirt, it doesn’t belong to either world. It’s what you wear when the occasion calls for something notational but, at the same time, not nothing.

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Dress it up

The polo shirt can look slobby, but with a little effort this piece can straddle the fence between sports gear and sartorial interest. First, go with one that fits properly: not skin tight, not a swimmer’s tank-top, and for God’s sake not billowing. Then, be sure to snag one that has some form of contrasting colour on the collar or the sleeve bands/cuffs. It should make it read as more deliberate, sporty, and not just another piece of baselayer babydoll bedsheet slop you wear because you’re too lazy to find a shirt. And for goodness sake, button at least one of those buttons – if you leave the entire thing open it just makes every dish you use and every kitchen counter you put it on look like a dirty mess.

Dark wash jeans and a solid or striped polo is the perfect low-effort style showcase; add field watch and aviator sunglasses to complete the scene.

Dress it down

Polo shirts are for in-between moments, when it’s not really a suit situation (then don’t even try), but you also want something that is slightly less casual than the T-shirt. A standard polo is cut pretty close to your body. And it’s supposed to be long enough that you can put your hands in your pants pockets without feeling overstuffed. Stay away from cotton/poly blends as these both show sweat more readily and, as they get wet, contain a mixture of poly fibres that smell like they came out of someone’s armpit. Look for natural fibres or at least a fibre that appears high-quality such as linen.

You can make the polo even more casual by pairing it with a pair of shorts. Make sure that the bottom hem is about at, or slightly above, the level of your pant zipper (or slightly through it, but not much below, or you’ll be wearing a nightie). Unbutton and untuck it, but make sure it’s tailored – a baggy polo will read much more casual than a tailored one. Finally, if you’re wearing it with a jacket, please don’t turn the collar up. The popped-collar phenomenon came and went with the express purpose of making you look like a douche.

Dress it up again

A polo is what you wear when something is ‘dressy casual’ – not quite a black-tie affair but not exactly ‘just lost my job and am moving back in with my parents casual’ such as a backyard BBQ or a summertime first date. You want to have a core group of polos in blue, black or white, but you can branch out to brighter colours or busier patterns. Otherwise, polos will read a little more casual if you opt for striped ones or those woven with a contrast between the collar/sleeve bands and the rest of the shirt.

It should fit snugly but not hug you – too tight and you give the impression of being squeezed into a bulging, phallic silhouette. On the same subject, the polo collar should ride high enough so that you can get a finger between it and your neck (no collar popping, and certainly no buttoning all the way up). Pair that soft, slouchy jacket with a polo in a natural fibre. Clash sharply with structured wool jackets – too jolting against the polo’s insouciant vibe.

Dress it down again

Rule of thumb: Polo shirts always fit, but never tight. A clean polo fits close to the neck and the chest and sits about midway down the fly/back pockets of your pants; your sleeves hit midways down your biceps and never longer than 2/3 of the way down your arm. Shirts with long sleeves are a sartorial no-go and play against the polo’s legacy as a warm-weather, sports-oriented shirt intended for athletic pursuits.

A polo shirt steps up from a dress shirt if you got something going on that doesn’t call for a button-down, but doesn’t quite feel like you have to wear a T-shirt. As for tucking, brokerage-bro tucking a polo just looks silly unless the shirt was meant to be tucked into pants (like jeans). Don’t tuck something that wasn’t meant for it – that slight leather you’re feeling is the cringe you’ll feel about it momentarily. Of course, your tuck should also take stock of the number of buttons on your shirt. Just because something undoes doesn’t mean it’s meant to hang loose. Leaving all the buttons undone is tacky and sloppy.

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