The Nines

One of Mark Twain's most famous maxims is "Clothes make the man." And he was right. But the best-dressed guy in the room is usually the one whose style is subtle enough to blend in, but bold enough to stand out. So, rather than let the barrage of holiday party requests make you stress your dress—and succumb to that old-school suit and tie—take a cue from these menswear pros on how to do Mr. Twain proud this party season.

Chinatown's answer to the concept store arrived barely a year ago when Brooklynites Brian Janusiak and Elizabeth Beer opened their latest collaboration, an art-meets-fashion, glass-windowed boutique. Have a peek inside and no matter what you're style, you'll be lured in by the pair's dutiful assortment of non-predictable guy-wear, from labels like Bless and Devandervar to Dangerous Sports Club.

Advice: "If you can't pull off a really bold holiday sweater…don't."
What to Wear: Gray leather coat by Hope ("Ever heard of Quadraphenia?"), $880, a subtle gray or black sweatshirt by Devandervar, $215, Various Projects Key-ring ring, $75 (gold) and $40 (silver).

Men's vintage usually conjures images of beat-up boots and T-shirts, but once inside Williamsburg's Houndstooth, visions of Gucci blazers, virgin flannel shirts, and barely tread-on tuxedo shoes will banish the former. The duo opened their Driggs Avenue store just over a year ago after Maria realized there was a men's vintage void among all of NYC's more girl-friendly treasure troves. "I kept having to turn away guy after guy that wanted a good vintage suit or cardigan," recalls Maria, who was then working at Poppet, a vintage shop in the East Village. "The men's market is experiencing a steady revival. We hope we're inspiring them to get out of their comfort zone of T-shirts and tennis shoes."

Advice: You don't have to go vintage head-to-tie. Try mixing up a great slim-cut blazer with a favorite shirt so you still feel like you, only better.
What to wear: Vintage velvet YSL blazer, $100 to $130. The pair also suggests a cowichan shawl collar sweater with a zipper detail. "They're thick enough wear as a jacket and make great conversation pieces." $85 to $150.

From an apartment behind his South Billyburg boutique, Andy Salzer creates a collection that has consistently delivered Brooklyn business wear season after season. So, it's no wonder that the designer himself prefers the semi-formal look for men on the town, or that he abides by the rule Less is More. "The holiday dress code can be so unpredictable," he says. Hence, Salzer advises, "Pay attention to your shoes. A pair of Converse in solid black leather is the easiest option: they match everything."

Advice: "Try to keep the color palette dark and simple—the only color really should be in the choice of tie. No crazy graphics, no bling-bling embellishments."
What to wear: "I sport my own jersey dress shirt and a contrasting jersey tie," says Salzer. White jersey dress shirt with tie, both by Yoko Devereaux, $128.

Since downsizing to a men's-only store this past year, South Willard's Ryan Conder has been upgrading his stock of essential menswear to include suits from Raf Simons, denim from A.P.C., and oxford shirts from Band of Outsiders. His well-edited selections couldn't be more on target with menswear's transition from grunge to groomed. But even with a store at his disposal, holidays, he affirms, are a challenge. "It's both a happy and difficult time, so I try to dress comfortably, but at the same time not too casual…I leave the too casual look to my dad."

Advice: "Don't wear anything that's going to make you feel uncomfortable or awkward…there are usually enough of those moments."
What to wear: Dark blue suit, $1,579, and white shirt, $335, both by Raf Simons.

How to be a handsome devil this holiday season.