How to Dress Like Harry Styles

by Jamie
An Open Letter to Harry Styles

At just 24 years old, Harry Styles isn’t just stealing teen girls’ hearts, he’s got grown men drooling over his laid back, ultra desirable style. Let’s dissect how you can steal Harry Styles style and get his rock star look without joining a band.

Harry Styles Outfits

Recently named one of the most stylish men in the world by GQ Magazine, the Worcestershire born Harry Styles clearly knows what’s up when it comes to dressing to impress. The One Direction crooner and style savant is not a trend-hound, rather, he’s developed his own unique blend of dapper and rocker that gives off the air of laid back luxury.

His foray into the fashion world is even documented on a twitter account called @HarryWoreWhat, with a following of 36,000 strong. But don’t let his cowboy boot and tattoo rocker aesthetic fool you, Harry Styles’s outfit favourites are high-end, buzzy brands like Saint Laurent and Gucci. Steal Harry Style’s clothes and style with our handy list of pointers.

His aesthetic is a double-headed sword. He can pull off ripped denim and his 56 tattoos for a Keith Richards rock God aesthetic, or he can suit up in a floral two-piece and still look just as good. He looks just as home in a Hawaiian shirt and cowboy boots as he does in a Saint Laurent suit. Here’s how to dress like Harry Styles for guys. 

Styles’ Style File

One of the most fun aspects of Harry Style’s style is he isn’t afraid to break gender norms. He added a long, silken scarf to his suit at the Billboard Music Awards, and he’s a frequent fan of billowing blouses.

You may have seen Gucci’s most recent collection sweep runways and street style blogs with their high-voltage seventies silhouettes. Styles has keenly adopted them, opting for vivid shirts and wide leg pants that go together as smoothly as butter and toast. Safe to say, Harry Styles and Gucci were a match made in heaven. When not channel the rock god look with leather boots, harry styles classic skinny jeans and Harry Style’s white t-shirts. Oh and don’t forget Harry Style’s bandana.

Harry Styles Shirt

Air Tie

For more formal occasions, Harry opts to rock a shirt-sans-tie look. The key to pulling this off is simple, just button your shirt to the top as you would when you’re about to put on a tie, then forget the tie!

Unbutton that Shirt

One of the key aspects to Harry Style’s laid-back style? Let loose and let those buttons fall open! Harry opts for four to five buttons, but you can steal the look but just letting one or two buttons worth of skin showing. Don’t forget to team your blue shirt with a classic Harry Styles choice of boots.

Hawaiian Shirts

You may have poked fun at your dad when he brought one on the last holiday, but it may be time to take it back.

The key to pulling off this flamboyant trend is to keep the trousers you choose to pair with it as minimal as possible. Chinos may lean a little too far towards dads-on-vacation, but a black skinny jean will elevate Harry Styles buttoned up shirt to street style status.


GQ dubbed Harry Styles the prince of prints, and for good reason. The dude embraces prints like they’re a plain white tee. Not even just your run of the mill print, he’s known to sport anything from gingham to leopard to paisley, Mr. Styles embraces them all.

For those who aren’t a typical print fanatic, ease your way into the trend with a subtle print like a plaid or pinstripe. Pairing a print with a black denim (a la Harry Styles) or black trousers is a great way to try out the trend without diving in headfirst.

For those wilder guys out there, try pairing a print with something out of the ordinary. Stack a printed dress shirt with a blazer! Perhaps even try out a colourful pocket square with a bold blazer?

Harry Styles T-shirt

There are times when Harry goes full on with the prints and bold shapes, and then there’s times where he just keeps it simple. With the right shape and styling, even a white T-shirt can look good, and Harry really knows how to pull off the minimalistic look. Pairing the simple top with a pair of skinny jeans and some good boots is a classic look for a reason, and if you focus on getting the right fit like old Harry here, then you’re sure to look simple and stylish.

Harry Styles Jackets and Coats

Harry Style’s go-to casual pieces show off his style flexibility. From YSL printed bomber souvenir jackets, to structured overcoats, Harry likes to jazz up a regular tee and jean combination with a statement jacket.

As much as he’s leather and bomber jacket fiend in his off time, Harry Styles knows how to turn up the class. He often opts for unfussy, neutral coloured overcoats. For the colder weather, a navy jacket with an oversized fit. One of Harry Styles clothing hacks – layer a structured or unstructured jacket with an old flannel shirt for a more relaxed feel.


Harry Styles wears almost exclusively black skinny jeans (seriously, we dare you to find a photo of him in blue jeans!) We don’t blame him: they’re a great canvas for exciting shirts and can carry you to any event, from a rock concert to supermarket.

Harry Styles Footwear

Styles’ footwear choices are just as rugged as his appearance. Distressed Chelsea boots, well-loved chukkas, and converse are all part of the daily rotation. Cowboy boots and leather army boots are well loved – scuff marks and stains are embraced.

One of the most common players in his shoe game? Little black boots, specifically of the ankle cut variation, with a small heel. Harry Styles pairs them with everything from slim jeans to suits. Take it to the next level by wearing a cowboy style boot, Heels aren’t just for the ladies! Rocking boots with a suit like Harry Styles is a great alternative to your traditional dress shoe.

Harry Styles Accessories

In true rock star fashion – Harry Styles is keen on the with-the-band accessories like jewellery, bandanas, and hats.

Bandanas are great when worn around the head, neck, arm or even around the leg of your jean. Make things every-day wear suited by choosing a neutral colour like white, olive or black.

Pro Tip: Although these trends are easy enough to pull off on their own, when worn together, they come off a little more Keith Richards 2016 than Keith Richards 1980.

Harry Styles Hat

Even though one of Harry’s signature looks is his flowing locks, he can pull off hats seamlessly. In the winter, find him rocking a beanie in tonal shades of grey or black. In the summer, the pop star tops his outfits with flat-brimmed hats or pageboy caps.

Harry Styles Scarf

When tackling the scarf Harry tends to keep things loose and relaxed, opting for scarves that frame the neck rather than strangle it. Keeping the material plain or sparingly patterned makes sure that the look stays neutral and versatile, and lets the scarf act as a complementary piece rather than a statement accessory.

Harry Styles Sunglasses

When it comes to sunglasses, Harry sticks to the classics, going with brands like Ray-Ban and donning the traditional shapes such as a wayfarer and aviator. He tends to steer clear of anything too patterned or uniquely shaped, with the sunglasses acting as a balance to his more colourful outfits

Lapel Pins

Even with a black suit, Harry adds some spice to a minimalistic suit with a floral lapel pin. As over-the-top as this trend may be, it’s surprisingly easy to pull off. If you’re not one for patterns, a white or black floral pin is a great addition to a traditional suit.

A thinner tie will modernise the look, and keep it from giving off an eighties school dance vibe. If you’re a prince of prints like Styles, pair a more vibrant pin with a patterned suit jacket or tie.

How to Dress Like Harry Styles

  • Break gender norms with looser shapes.
  • Mix bold prints with simple apparel, such as a patterned shirt with simple skinnies.
  • Accessorise with simple accessories to pull your outfit together, such as jewellery and silk scarves.
  • Ankle boots with a small heel go with everything so consider investing in a pair.

On That Note

There you have it, a wide range of Harry Styles inspired outfits Dressing like the young rock star is easier than you think. Even though his casual style is a mélange of basics, he pulls them off with a confidence and originality that makes them all his own. He’s got his go-to – the man jewellery, the leather chelsea boots, and the over-sized flannels, but he knows how to pair them for that perfect woke-up-like-this flair.

The key is in variation – Harry Styles also knows how to break out of the box when he suits up. Instead of typical bad-boy leather for his night out looks, the young singer opts for feminine, whimsical florals.

Even if you’re not a One Direction fan, you have to admit the dude looks good. Follow these simple tips and you too can steal Harry Style’s laid-back, rock star style.

Feature image from Pinterest

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