The Only 5 Suits You'll Ever Need to Own

This is the workhorse. It'll get you through everything from evenings out to job interviews, plus, the color looks great on everyone. Choose a breathable wool that's not too heavy, and it'll carry you through all but the coldest winter nights and swampiest summer days. Just don't ever button the bottom button.

SHOP Napoli Blue Plain ($399) by Suitsupply, suitsupply.com

Nothing says warm weather like a crisp cotton suit. Khaki's the classic color here, for good reason. It's appropriate for the office and has enough of an edge to pull double-duty on weekends. Try it with a patterned shirt and a pair of white canvas sneakers to show the world you're dressing up because you want to, not because you have to.

SHOP Ludlow Suit Jacket ($298) by J.Crew, jcrew.com

SHOP Ludlow Suit Chino ($158) by J.Crew, jcrew.com

There's no better way to prove you've got tailoring chops than by rocking a double-breasted suit. Today's versions are trim, comfortable, and designed to hug your shoulders, not swallow them. It's still a power move, though, so if you feel like going for, say, an understated Prince of Wales check, we're not going to stop you.

SHOP Embroidered Prince of Wales Suit (2,980) by Gucci, farfetch.com

Once the uniform of the American salary-man, the grey flannel suit is now a bit more rebellious, much more stylish, and still totally versatile. Throw on a white shirt with a black knit tie, and you've got a perfect nine-to-five look. For weekends, layer with a sweatshirt or break it up and wear just the jacket.

SHOP Rocco Flannel Suit Jacket ($1,490) by Salle Privee, mrporter.com

SHOP Rocco Flannel Suit Trousers ($615) by Salle Privee, mrporter.com

Skip the rental game and buy a tux instead. It's an investment, but you won't just be buying a suit: you'll be investing in a better-looking you. Make sure to get something that'll age well. Black is a solid bet, but midnight blue is great, too. Go for peak lapels or a shawl collar, avoid unnecessary embellishment, and you're golden.

SHOP Two-button tuxedo ($3,680) by Prada, matchesfashion.com