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How To Wear A Hoodie & Not Look Like A Hooligan

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1 of 20|Thom Browne|Striped Loopback Cotton-Jersey Zip-Up Hoodie
2 of 20|Vetements|Oversized Printed Loopback Cotton-Blend Jersey Hoodie
3 of 20|James Perse|Supima Cotton-Jersey Zip-Up Hoodie
4 of 20|Saturdays NYC|Ditch Striped Loopback Cotton-Jersey Hoodie
5 of 20|The Elder Statesman|Speckle Slub Cashmere Hoodie
6 of 20|Loro Piana|Cotton And Cashmere-Blend Zip-Up Hoodie
7 of 20|Champion|Reverse Weave Classic Hoodie
8 of 20|T By Alexander Wang|Scuba Neoprene Hoodie
9 of 20|Moncler|Bonded Cotton-Jersey Zip-Up Hoodie
10 of 20|Rick Owens|Drkshdw Embroidered Popover Hoodie
11 of 20|Off-White|Brushed Diagonals Zipped Hoodie
12 of 20|Public School|Ollan Checked Textured-Flannel Zip-Up Hoodie
13 of 20|John Smedley|Textured Merino Wool Hoodie
14 of 20|Venroy|Cashmere Knitted Hoodie
15 of 20|Club Monaco|Loopback Cotton-Jersey Zip-Up Hoodie
16 of 20|Suitsupply|Cashmere Silk-Cotton Blend Raglan Sleeve Hoodie
17 of 20|Outerknown|Striped Cotton-Blend Terry Zip-Up Hoodie
18 of 20|Polo Ralph Lauren|Fleece-Back Cotton-Blend Jersey Zip-Up Hoodie
19 of 20|Neil Barrett|Bonded Jersey Zip-Up Hoodie
20 of 20|John Elliott|Kake Loopback Cotton-Jersey Hoodie

Comfort-lovers rejoice. Men’s fashion is relaxing even more. Sportswear’s looking a lot more like luxury and luxury’s now kicking back into leisure mode. Which means the (once sloppy) hooded sweatshirt (or hoodie) is yours for the luxurious taking. But, before you start getting comfy on the style couch, there are a few fashion rules to follow when investing in today’s hoodie.

First up, let’s talk a brief history of the hoodie, followed by the main components to make up the luxury hoodie — from fabric to form to fit. Then, there are some do’s and don’ts when talking how to wear the hoodie too. And, it’s anything but college jock.

The History


The hoodie had humble beginnings. Champion began making sweatshirts in the early 1930s, adding the hood to its sweatshirts to protect athletes and labourers from the elements. Meanwhile, college sporting teams began asking for warmer apparel for winter too, leading to the hoodie being adopted by most of sixties’ young America.

By the seventies, hip-hop culture was developing in the streets of New York. Here, the hoodie was popularised by graffiti artists, break dancers and trouble-makers, all wanting in some way to eschew the police, concealed by hoods. By the eighties, renegade skaters were hoodie purveyors too, while the hard-edge gangsta rap of the nineties cemented the hooded sweatshirt as a sign of societal rebellion and subculture inclusion.

Fast forward twenty years, the hoodie’s cloaking abilities and incredible comfort make it a practical and stylish top for men.

What To Look For


Performance and invisibility aren’t the only priorities for today’s hoodie. “When shopping for your next hoodie, look for quality craftsmanship, a nice fit and versatility,” explains Sean Venturi, co-founder of Venroy in Sydney.



The zip variety, much like blazer, is designed to be worn open or zipped depending on the weather and overall outfit.
“You can wear the zip-through smartly. And, it’s more versatile — you can take it off without messing up your hair, and unzip once inside if you start to feel warm,” says Sean.

The pullover variety is slightly roomier in shape. Higher neck lines, slide slits and the absence of a ribbed hem are more common with this type too, elevating comfort over class.
“This style is the iconic hoodie style and is associated with staying warm and cosy. Ultimately, it should be kept at home. That said, still look around for a sophisticated version. Hoodies are about sophisticated comfort — looking good while lounging on the couch.”



As a rule: the hoodie should to be fitted. Shoulders should be snug, with the sides of the hoodie following the drape of the torso. A billowy body immediately creates a sloppy, weekend dad look. Functionally, it makes layering tough and messy, creating bunching, rolls of fabric when placed underneath a topcoat or jacket. If the hoodie is your outerwear piece you can afford more room. Every guy should have one fitted and one relaxed hoodie, to have both style bases covered.

“Again, think comfort. Never go for a super tight fit. But, a nicely fitted hoodie is a far better look for dressing up and dressing down. If you’re wearing a long sleeve shirt, you want to have enough room to get your hand up the sleeve, comfortably. And, the fit needs to allow for over-layering, chucking on a jacket, smoothly, over the hoodie, without bunching,” says Sean.



You also need to pick the right fabric. Cotton jersey is the original (and the best). It’s loved by athletes and now urban gents alike. The cotton stops air from penetrating (thus, keeping warm), it absorbs sweat, and is breathable when body temperatures warm up underneath. Plus, jersey is super comfortable. Look to loopback cotton (it will say so on the tag) for the transitional seasons – spring or autumn.

“Look for a hoodie that’s ‘fully fashioned’, where the hoodie’s material pieces aren’t just cut and sewn together. Instead, they’re knitted together at the seams. For example, a waffle knit. Cashmere is the ultimate in the refinement. It just looks more high-end,” says Sean. “So, opt for a cashmere-cotton blend — soft but durable. Ans, as a waffle knit, it’s instantly more breathable too.”

Hoodie Do’s & Don’ts


No longer just for the gym (or couch) junkie, the hoodie can be worn in the street, to a nice restaurant and even to (some) work places. Here are the hoodie do’s and don’ts for the contemporary man:

  • Do consider the purpose of your hoodie. Streetwear? Look for more relaxed, cotton jersey fits. Smart? Opt for cashmere or silk-cotton blend, for a better quality, nicer looking finish.
  • Do wear it with tailoring, worn as a blazer with a shirt and tie. As an inner layer piece, it’s a sporty alternative to a waist coat or cardigan — just be sure to have the fit snug and the hood neatly hung at the back of neck.
  • Do wear it as an off-duty jacket. Team over a basic t-shirt, washed denim and suede boots or sneakers.
  • Do learn to layer it. Hoodies are the ultimate ‘meat’ piece in you winter layer sandwich. The parachute silk parka or waterproof mac coat are great options, keeping your hoodie dry in bad weather.
  • Don’t be afraid to mix high and low pieces together with the hoodie. Smart-cum-casual is the hoodie’s speciality.
  • Don’t forget the hoodie is a casual piece. As soon as you add it to a formal, semi-formal or smart casual outfit, your look is immediately knocked down the dress code spectrum. That’s not to say it isn’t a good idea, style-wise. Sports wear is here to stay in menswear. Just be aware of event expectations and social acceptances before you decide to wear a hoodie with your tux. Ok, don’t ever do that.

Expert Style Tip

“Despite it being casual, the hoodie does fair well with smarter items. With tailoring, opt for a deconstructed blazer: no shoulder pads, in lightweight fabric and with a relaxed sleeve, because a double sleeve — with the hoodie sleeve underneath — can look and feel bulky under a suit jacket. Team with tailored trackies and low-cut sneakers and you’ve got a hot sportsluxe look. You could even throw in a pocket square.

“More casual still, work the hoodie under a leather jacket or bomber, mixing in chinos or jeans. You need to keep the look clean, which means absolutely no logos or brash branding. Lastly, avoid dress shoes. Opt for dessert boots if you’re not one for sneakers. And, leave your loafers at home, gents.”

Jeff Lack – Stylist @jefflackstylist



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