It takes a special kind of man these days to just wear a suit, you know, around. If you aren't in finance or law, you probably don't even find much of a chance outside the usual wedding, funeral or job interview, and if you showed up to dinner wearing a suit your friends would probably laugh at you.

But why does it have to be that way? Looking good builds confidence, it gets you places and it makes people jealous. Whether you already love dressing to the nines or you're looking to graduate to the next level, here's how and where to wear a few different suit styles around town this year.


DATE NIGHT

Like where? Lincoln Center, Locanda Verde, Blue Hill, Broadway.

Wear this.

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Essential Gray Prince of Whales. If you're taking out someone special, it's good to look your best, and there's not much better than that "royal look." Of course, not every date calls for a suit, but let's assume this is a nice one: an anniversary, once-a-year dinner reservation, a show, a night of dancing. Having already locked down an awesome significant other, you can let go of some inhibitions; the bravado of pattern paired with a few nontraditional accessories will make you stand out from the schlubs around you—certainly something your date can be proud of.


OUT WITH THE GUYS

Like where? The Standard, The Delancey, Keens, The Brandy Library.

Wear this.

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Navy blue sharkskin. Celebrating a new baby, a promotion, a love of porterhouses, or just being alive? You're probably someplace fancy. Navy is an excellent entry level suit that's wearable pretty much anywhere, but if you want to look masculine, statuesque and right at home sipping whiskey in a tufted leather booth, there's no choice better. White and preppy red accents will keep things looking classic Old New York—and save you from a night of heckling for your purple paisley.


HIGH SOCIETY WEDDING

Like where? The American Museum of Natural History, The Four Seasons, The Pierre.

Wear this.

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A black tuxedo. Nothing says "please don't look at me" quite like renting a tuxedo for your boss's wedding. There are a few occasions in life that require black tie and if you know the right people, work in the right industry, or live in New York, it'll happen to you. Instead of feeling uncomfortable in an ill-fitting sack all night, get your own tux, and get it custom-made. The price here is surprisingly affordable, and it'll take you all but five minutes and a shave before every reception to make the groom wish he were you.


WEEKEND GETAWAY

Like where? The Hamptons, Cape Cod, anywhere on the Eastern Seaboard.

Wear this.

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Beige pebbleweave. Vacation is one of the best excuses to mess around with your personal style. No one knows you, you're doing out-of-the-ordinary stuff, and everyone around is guaranteed to look a dad at Disneyland. Take the opportunity to sport a summer menswear classic: tan. You can go with linen, but the pebbleweave here is similarly lightweight and a bit more put together in case you find yourself out to dinner or crashing a New York Times couple's beach wedding.


WILD CARD

Like where? Jazz Age Lawn Party, Fashion Week, Sleep No More... who knows?

Wear this.

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Olive linen, patterns, loud accessories, you name it. You love to dress well and you're ready to ascend to Suit Level 1000. Find an event where novelty is part of the game: channel Gatsby at the Jazz Age Lawn Party; try to get on a street style blog at Fashion Week; pretend to be someone else at some heady interactive theater. And really, even the olive here is conservative. Maybe next time try burgundy, corduroy, even plaid—at this point, you've got the talent.


This post is a sponsored collaboration between Indochino and Gothamist staff.