How to get the unique look of everyone’s favorite smartly-dressed smart-ass, Gossip Girl‘s Chuck Bass.

#32 “I’m Chuck Bass.”

Have you ever wanted to channel the suave sophistication of Gossip Girl’s resident bad boy, Chuck Bass? Would you like to be the target of men’s scorn, the object of women’s desire, and the uppercrust’s most scandalous teenage billionaire? Well, who can blame you? He’s Chuck Bass: conniving, cold… and incredibly chic. Even the virtuous among us can’t help but find this Mother Chucker’s wardrobe truly envy-inspiring. Read on for our tips on how to dress like the one and only Chuck Bass. You’ve got some pretty big (and expensive) Armani loafers to fill.

#31 Everyday Wear: Every Day is Designer.

When you’re Chuck Bass, casual can never mean careless. Whether you’re spending the afternoon at the gentleman’s club or just lounging at home, it’s essential to look sharp at every moment. That means well tailored, well coordinated, and well groomed. You never know who might come calling. Let’s take a look at the keys to Chuck’s favorite everyday looks.

#30 Everyday Wear: The Suit Life of Chuck Bass.

If their New York worlds ever collided, I think How I Met Your Mother’s Barney Stinton and Chuck Bass would be great friends. Why? Because they both love three things, above all: hot women, luxury booze, and the perfect suit. So, if you want to embody the Bass in your everyday, take Barney’s advice, and “suit up!” Perfectly tailored and insanely expensive, if possible. Don’t even bother if you’re not going all the way with a tie, bowtie, or ascot. And always a pocket square. Always.

#29 Everyday Wear: Layers, Layers, Layers.

Your clothes should reflect your enigmatic personality: infinitely and seamlessly layered. Observe this ensemble. Notice how the vibrant blue cuffs and red pants play off the stripes in the shirt, and the muted sweater keeps the brights from overpowering. Everything “goes,” without being too forced.

#28 Everyday Wear: Earn Your Stripes.

Don’t be afraid to mix patterns. Chuck loves stripes, and this clean-cut seersucker look is a perfect example of his penchant for pairing different colors, widths, and angles of stripes.

#27 Everyday Wear: Old School Sexy

Borrow a page from a bygone era for a really striking statement. The key? Accessories. Here, the hat, the ascot, and the perfectly polished leather shoe create a classy 1940’s Clark Gable look, which is perfect– because frankly, my dear, Chuck Bass never gives a damn.

#26 Everyday Wear: Taste the Rainbow.

Color is your constant friend, so you better learn to coordinate. A burgundy blazer with a light pink button-down is the perfect ensemble for mid-morning brunch–and guarantees you’ll get served that cocktail you need to complete the look.

#25 Everyday Wear: Pink–Not Just for Princesses.

You’re Chuck Bass. You’re so comfortable in your masculinity that you shower in a special mixture of scotch and testosterone. That means no color is beyond your fashion domain. A flash of pink can be dapper if not overdone.

#24 Everyday Wear: Gray Doesn’t Mean Drab.

A gray suit is the perfect canvas to look boldly stylish, without going sissy, with a bright contrasting shirt and tie.

#23 Everyday Wear: Well, Orange You Charming?

Chuck Bass knows there’s no better way to woo the girl than to make a big impression with vivid fashion choices. How to go from better to best: when your jacket goes with the flowers you bring when you pick her up in your limo.

#22 Everyday Wear: Seafoam Dream.

The master of his domain is also the master of the full color palette. An unusual shade like seafoam green is striking but subdued enough to merit a full suit. This crisp, springtime look is best done outdoors, to complement the shades of nature.

#21 Everyday Wear: Blue Blood Beautiful.

It’s important, on your busy days, to stay sharp, but versatile. A man who can go from sailing to sexcapades in the course of an afternoon needs an outfit that can do the same.

#20 School Wear: Uniform Advantage.

Sometimes even the young, rich and powerful have to make an appearance in the hallowed halls of overpriced academia. So how do you take a mandated school uniform from blasé to Bass? Check out Chuck’s best St. Jude’s looks.

#19 School Wear: Chino Chic.

The Devil himself is in the details. A patterned khaki and vest make this uniform anything but. Put the icing on your cake with a stylish man-purse–err, carryall.

#18 School Wear: Change Up the Button-Down.

Don’t be afraid to take risks with cut. This curved spread collar may turn some heads in a bad way, but Chuck Bass isn’t one to shy away from bold choices in an otherwise ordinary look.

#17 School Wear: The Signature Scarf.

Chuck knows there’s nothing wrong with a man who can pull off a scarf. His signature silk is the perfect hybrid of classic colors and modern pattern. Goes with the uniform–and takes it beyond.

#16 Business Wear: Cover Up Classy.

So you’ve suddenly become the youngest CEO in New York City, and you desperately want to be taken seriously by your investors, employeers, and scheming, back-stabbing uncle. What to do? You don’t just mean business, you dress it, too. A tan wool coat that costs more than most people’s cars should do the trick. Here come more of Chuck’s business wear tips.

#15 Business Wear: Fit Like a Glove.

Still not getting your way at Bass Industries? Look wise beyond your years in a a serious khaki trench with black piping, and black leather gloves.

#14 Business Wear: Slick and Sleek.

But don’t forget yourself–you’re still Chuck Bass. Break out a bowtie and a pink shirt–you know you want to. But keep your flair in check with a subdued double-breasted gray peacoat, and an all-business slicked back hair style.

#13 Business Wear: Purple Reign.

Nothing says New York royalty like a dash of purple in your pocket. Command respect wherever you go, from the boardroom to the burlesque club you just bought.

#12 Business Wear: Fit to be Tied.

A little goes a long way. Skipping class for a business lunch? A paisley tie keeps it festive, without getting too flamboyant.

#11 Business Wear: Show Some Plaid-ittude.

A plaid jacket at an evening cocktails meeting guarantees you’ll look like a seasoned member of the old boy’s club–even when you’re still a few years shy of 21.

#10 Pleasure Wear: The Robe–Not Just for Hef.

Plotting the downfall of your enemies is exhausting, and even Chuck Bass needs time to recuperate–in lavish luxury, of course. A red velvet robe can be suggestive without getting too sleazy. Just make sure it’s tied. He’s a man of many pleasures. Read on for more of Chuck Bass’s favorite hedonistic garb.

#9 Pleasure Wear: Playboy Playful.

Chuck looks red-hot on a night out at Vitrola in a black blazer and red button-down. The key here is to keep it simple–and your stare smoldering.

#8 Pleasure Wear: The Velvet Lounge.

The man clearly has a thing for red, and we can see why. Drink in hand, this velvet blazer is perfectly plush, and the muted color keeps it from getting too self-indulgent. Chuck has other indulgences to consider.

#7 Pleasure Wear: White Hot.

Aviators? Check. Ascot? Check. Well-aged scotch? Check. All white suit with black collar details, swept-back hair, and a sexy smirk? Checkmate.

#6 Formal Wear: If the Shoe Fits…

Women have known it for a long time: the shoe makes or breaks the outfit. And no one knows fashion, or formal wear, better than Chuck Bass. The man who lives in designer suits must work to make his tux and tails all the more extravagant–and perfectly accessorized, as always. Ahead, learn the secrets of the Bass tuxedo library.

#5 Formal Wear: All that Glitters is Not for Girls.

Nothing says “special occasion” like a sequined tuxedo jacket. A normal guy’s sexuality might be called into question for such a choice. But you’re Chuck Bass. Everyone knows that heter-opulence is your M.O.

#4 Formal Wear: The White Glove–Not Just for Michael.

Take your tuxedo to the next level of Manhattan elite with some white gloves. Perfectly coordinated with your white bow tie, of course.

#3 Formal Wear: Black and Dapper.

A funeral is no excuse to forget your fashion philosophy. Pair stripes in blacks and grays for a somber yet sexy ensemble.

#2 Formal Wear: Tux and Tails.

It’s easy to give a simple black tux your signature rakish twist with a patterned bowtie.

#1 Formal Wear: Rich Kid Blues.

But why stick with basic black? This blue one-button jacket is perfectly polished, playful, yet professional–the epitome of Chuck Bass fashion, tied with a bow. How could Blair resist? Click through to rearrange the slideshow in order of your favorite Chuck Bass looks!

Meghan Carlson

Senior Writer, BuddyTV

Meghan hails from Walla Walla, WA, the proud home of the world’s best sweet onions and Adam West, the original Batman. An avid grammarian and over-analyzer, you can usually find her thinking too hard about plot devices in favorites like The OfficeIt’s Always Sunny in Philadelphia, and How I Met Your Mother. In her spare time, Meghan enjoys drawing, shopping, trying to be funny (and often failing), and not understanding the whole Twilight thing. She’s got a BA in English and Studio Art from Whitman College, which makes her a professional arguer, daydreamer, and doodler.