They say if you can put a celebrity or public figure in a certain outfit and then know whose style they are channeling, then that look has become iconic.

Now, if you saw Obama or Tom Cruise in a red silk robe rocking velvet slippers, it would take you all of two seconds to know he was dressing like Hef. That’s the power of having your own personal style, something HH knows all about.

In honor of the bossman’s 91st birthday, we wanted to celebrate Hef’s inimitable swagger by showing you how to rock and style his most iconic looks.

A good tip for any dude: part of what makes Hef’s style so dope is that he knows that you know he’s “getting away with it.” We take his sartorial brilliance for granted nowadays, but back when dress codes (and social taboos) were much stricter, Hef proved that you can curate an entire wardrobe around being a man of leisure and still be taken very seriously.

Check out our roundup of five Hef-approved sartorial nuggets, and dress for your best life, right now.


Belgian Shoes

Belgian Shoes

CREATIVE LOAFING
Nothing says casual elegance like a pair of chic loafers. To really nail the Hef look, you want to steer clear of the preppier versions (often called “beef rolls” for their chunky accents) and get something super slick with minimal distractions. And for that, there’s no better brand than Belgian Shoes, who have been making their super clean loafers by hand for over 300 years. Get a good return on your investment by copping a pair in navy or tan, both look great with denim and a T-shirt.


Ralph Lauren

Ralph Lauren

SMOKED OUT
You need at least one killer smoking jacket in your wardrobe. “But why? I’ll only wear it a few times!” you say. We say: be like Hef, flout convention, and wear a smoking jacket to unexpected places—and with casual pieces like loafers or T-shirts. You can even pair it with jeans for a perfect high/low look. Many brands offer smoking jackets in classic colors like black and navy, but to really make it pop, we recommend a wild pattern, like this exquisite floral jacquard number from Ralph Lauren
Mr Porter

Mr Porter

PAISLEY IN FULL
You wouldn’t think that a titan of industry like Hef would have too much in common sartorially with shabbily chic rockers, but they both share a love of paisley shirts. And who can blame them? Not only do they look rad, they can be styled up or down with ease. So long as the colors are pretty subdued, you could totally wear one to work with some crisp chinos, or rock it up with some very on-trend chelsea boots. Hef would often pair his with a solid blazer, a bohemian business look we can definitely get behind.
Loro Piana

Loro Piana

ROBE LIFE
Hef’s red silk robe might be so iconic that you can’t really wear one without biting his steez. Good thing brands are now producing lux robes in everything from humble terrycloth to godly cashmere for today’s man of leisure. On the neo-hipster tip, we love the retro-inspired offerings of NYC-based Sleepy Jones. And for the real playaz, you can never, ever go wrong with a high rolling cashmere robe from a super lux brand like Loro Piana.
Brooklyn Tailors

Brooklyn Tailors

SUIT YOURSELF
While he may have made his name and image by turning loungewear into business attire, Hef has always known that in certain occasions, there’s just no substitute for a classic blue suit. Classic should never mean snoozy, so steer clear of flat tones and instead, let the texture and subtlety of the fabric do all the talking. Boutique brands like Brooklyn Tailors are killing it right now making affordable, vibey suits that are as youthful as they are office appropriate.