Traditional Prepster

Forget your high school valedictorian with his too-tight blazer and pleated front khakis that stopped right where his white sport socks began. Boarding school prep is all about the rebel in the back of the class who may have complied with your school’s dress code, but just barely. Sure, he had the worst grades in the class, but in terms of style, it was all A’s across the board. Preppy is no longer centered around the uptight WASP-y rules of the eighties, nowadays it’s all about modernized classics that are clean, fitted and deceptively simple. Pay attention to fit, utilize traditional, country club-approved separates and add a hint of insouciant JFK cool by finishing the look off with a pair of classic Ray-Bans. But don’t be afraid to let your inner bad boy come across in little ways! Details such as lapel piping, a vintage push-pin or perfectly positioned tie bar or formal suiting paired with Hypebeast-worthy kicks will let everyone know you may vacation in the Hamptons, but you’re just as at home at a Williamsburg warehouse party.

Italian Gent

The key to achieving the look of  an Italian gentleman is sharp tailoring and classic suiting pieces that are made uniquely your own with fun flourishes and unexpected touches. This look has been mastered by older Milanese gentlemen and scions of style like Lapo Elkann. A simple, no-brainer outfit of a spotless white Oxford Shirt, jeans, a dark blazer and designer loafers transforms into a remarkable ensemble after the Italians have added their uncanny sprezzatura touch. These men have so fully absorbed the traditional elements of good style and the necessities of a well-tailored suit, they’re able to ramp up those standards to new, daring levels and give them their own customized spin. The other part that goes hand in hand with good style for these Italian uomini is a willingness to be bold and outlandish, letting their own taste shine out of every detail, without fear of the ramifications. Never trendy, but also certainly not stuffy, the Italian gent mixes stripes and polka dots with abandon and will rock a rolled up suit pant sockless, but somehow always looks like he’s wearing head-to-toe custom menswear couture. The Italian Gent seems to always look totally effortless but also perfectly on point, testament to the reason Italy’s been one of the world’s fashion capitals for centuries.

Back to Basics

Imagine if a young Marlon Brando or James Dean became the muse for Alexander Wang’s undeniable brand of cool. When going for classic basics, that’s precisely the meeting of minds you should be aiming for. Look for sharp, architectural lines done in monochromatic black or white with a decidedly streetwear bent. Everything head to toe should be crisp, fitted and clean with an emphasis on wardrobe staples like the simple white tee, straight leg, dark blue jean and sneakers or chukkas in a sturdy, neutral fabric, like leather or canvas. Mastering this look is about investing in wardrobe essentials; timeless pieces that will endure and only ameliorate with time. Go for pieces that will never steer you wrong, borrowing style cues from Cary Grant and mixing them with the attitude of a young Bob Dylan. And just because you’re keeping your look understated, don’t feel as though you can’t let your personality peek around the edges. Mixing in an unusual piece with this neutral palette allows it to make even more of a statement, like a splash of red paint across a white canvas. Bottom line, don’t overthink it. It’s time to pare down your wardrobe and get back to basics.

Biker Badass

There’s a reason why the rebel biker aesthetic has endured for decades and withstood countless trend cycles. Inspiration for this look comes from classic 1960s images of Peter Fonda in cult classic Easy Rider and Steve McQueen cruising on his Triumph motorcycle come to mind. Take a style cue from these sartorial badasses and go for total Biker cool in all black everything. Black on black may sound dull and boring, but the effect is timeless, avant garde and powerfully cool. Plus, the monochrome uniform allows the true cut and style of your clothing to shine through, letting layers and unusual style details to unexpectedly pop. Of course, black is great, but the real trick to securing your status as a bad boy heartthrob is to finish everything off with a classic leather jacket and, for the brave, a pair of durable leather boots. For the jacket, stick with a fifties greaser cut, anything too trendy, accessorized or unusual will draw all the attention away from you and is sure to feel outdated in under a year. For boots, go with something practical and not too bulky, lean more towards something like Dr. Martens and away from the traditional Frye motorcycle boot which could make your outfit seem over the top and costumey.

The Urban Lumberjack

The Urban Lumberjack’s uniform needs to be as tough and rugged as you are. Flannel and Timberlands are just par for the course when you need to be able to make the seamless transition from the office to the log cabin you built in the blink of an eye. The outdoorsman look is pure Americana, so brands like Levi’s, Ralph Lauren/RRL and Red Wing are going to hit the nail perfectly on the head. To keep your aesthetic from veering too much towards unkempt grizzly man, try to find pieces that happily marry modern, urban trends and practical sportswear. Think of utility jackets in luxury fabrics, Saint Laurent’s grunge-y plaid button downs, and Mark McNairy’s boot collaboration with Eastland. City or country, subway or tractor, Gant or Carhartt, your ability to casually pick and choose from both ends of the spectrum and merge them together is going to help you achieve the chic Brawny man look of your dreams

Downtown Artist

There’s a reason why the Lower East Side and Williamsburg have become a hotbed of street style activity. The neighborhood known for housing students, artists and musicians is just as vibrant and diverse as its inhabitants would suggest. The Downtown Artist look lives in the unexpected. Nothing is too outlandish, too monochromatic (see above) or too eccentric for this bohemian set. The aesthetic is a hodgepodge of pieces that somehow play off each other to perfection. The style pulls from all kinds of sources, combining vintage and thrifted finds and designer hand-me-downs with original, one-of-a-kind pieces from your fashion design school friends. No two downtown aesthetics are ever the same, each individual borrows from all the various aspects of their life to create something thoroughly original. For the creative type, their wardrobe is the medium they use to hone and finesse their vision into a form of creative expression just as sincere and important as any piece of artwork they produce. The results tend to be nothing short of a masterpiece.

Surf Influence

Surfwear gets a bad rap, often conjuring images of California hippies and dudes who think board shorts and flip flops are black tie attire. But the surfwear trend is making a major fashion comeback, showing everyone that when the surfer attitude floods the runways and spills over into the streets the result doesn’t have to look like Lords of Dogtown. The trick to keeping the surf look chic and never shabby? Mix some of your beach favorites in with your more dressed up pieces and remember fit is everything. Pair boat shoes with khakis and a boldly striped tee, boardshorts with a button down, or even a hawaiian shirt with your sleekest blazer. Surf influenced fashion shows that your wardrobe should be as multifaceted as your personality. Don’t be afraid to mix up classics with nautical pieces that showcase and are true to your personality. The interest comes from the mix of high and low, and more fashion-forward pieces paired with athletic wear. So go ahead, hang ten, brah!

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