For men, the key to looking sharp for New Year's is dressing appropriately for the destination. "I've seen guys in suits in bars where there's really no need for you to dress up," said Phillip Williams, director of client relations at men's store Haberdash, which has locations in the Loop (607 N. State St. 312-624-8551) and South Loop (150 W. Roosevelt Road 312-357-5134). "And vice versa, where guys show up very casually at something where everyone is dressed like an adult for the most part."
Not sure how fancy-pants the party you're attending will be? "You can never go wrong wearing a jacket, a tie and a nicely pressed shirt on New Year's Eve, ever," Williams said. "But I think that if you are going to something that's a little more formal, you should definitely don a full suit—you can't do just a jacket at that point, because it's something a little more elegant." The standard black suit isn't your only option. "Black suits are nice, [but] I wear black suits to funerals, I'm sorry," Williams said. "Unless it's a black-tie affair, I'm going to do something ... that has some color, that has some life to it, because it's a party! You're celebrating the fact that you're on this earth for another year. Come on, have a good time!" For a seriously sophisticated party, Williams put together this bold outfi t (all items available at Haberdash) and doles out his advice on putting together a similar one of your own.
The components of a three-piece suit—jacket, vest and pants—can be worn on their own, but exude class when you pair them all together. Williams suggests buying your suit at least two weeks before New Year's to leave time for alterations. When shopping for a patterned suit, look for pinstripes that are subtle; if they're too thick or bright, it can come off looking like a costume.
"If your pants and jacket are solid, then your vest should be a slightly different color," Williams said. "But if they're patterned, you kind of have to stick with the pattern." You can also typically buy your vest one size down from your jacket size, and Williams prefers to leave the bottom button undone.
Pictured: Winston stripe vest, $178
Fit is key. "Your jacket should be fitted but not overly snug," Williams said. Your sleeve should hit right where your thumb meets your hand, so just a quarter inch of your shirt sleeve peeks out. "As far as the length of the coat, there is some wiggle room for that, but ... the length is usually about 29.5 to 30 inches from the base of the collar to the bottom of the coat. That's considered a modern cut, because what it does is it stops maybe just below the top seam of your back pockets, so it doesn't completely cover your butt."
Pictured: Hackett chalk stripe jacket, $498
Williams suggest slim-fitting—but not skinny—pants. "Unless you're the type of guy that you're a 29 waist and you're a buck-forty wet, there's no need for you to wear skinny pants. Save that for the jeans."
Pictured: Oliver stripe pant, $198
"You want to make sure your shirt fits well, because let's face it, it's a party, you're having a good time, eventually your jacket's going to come off. The last thing that you want is you have on a nice-fitting suit and your shirt's just blousy and hanging out everywhere," he said. If you're wearing a patterned suit, pick a solid shirt. "A patterned shirt with a patterned suit? It can be done, but if you don't do it right, you risk looking like a fool."
Pictured: New England for Haberdash shirt, $168
Before you chicken out and grab your go-to necktie, let Williams make his case for the ascot. "What do you say to a guy in an ascot? Nothing, it's a [bleep]ing guy in an ascot. He didn't take the light way out and put a tie or a bowtie like everyone else," he said. "And the best part about the ascot for [later in the] night, boom—you just take it off and throw it to the side. Your shirt is open—that's OK, because the rest of you is still put together, and you're not as stuffy as the guy over there trying to throw his tie back while he's dancing."
Pictured: Haberdash ascot, $138
"You can wear a brown shoe with a navy pinstripe suit and it'll look great. You can wear a tan shoe and it'll look good. But the bourbon—awesome. It adds that extra level of sophistication ... and it's a color that not too many people are wearing these days." The cap-toe style also adds visual interest. "If it were a plain toe, it would look a little tuxedo-ish. The cap toe gives it just that sort of edge but without going over-the-top."
Pictured: Allen Edmonds Park Avenue cap-toe oxford in bourbon, $345Copyright © 2015, RedEye