Where to be Well-Dressed in New York this Season

Where to Meet People That Own More Than One Suit

Sometimes you just need to go somewhere you feel you belong. While social clubs aren’t what they used to be (I made the mistake of asking my grandfather where he frequented when he was a young man), there are still plenty of places a well-put-together gentleman such as yourself can see and be seen by others who will appreciate the effort you’ve made to be presentable in an elevated environment. The following list comes from my own experience and from well-dressed friends whom I hold in the highest esteem.

For liquor and music

The Django, Tribeca - one of the first places I went where I felt the feeling. While TikTok has democratized this place, the martinis come in huge glasses and are made with care by a bartender in a bowtie. You’re paying for the unique atmosphere: listening to Jazz in what looks and feels like an underground cave makes for great acoustics, and the audience is expected to be fully engaged. The music is top-notch, even better after a burger and a few cocktails. Reservation recommended Thursday through Sunday; midweek, you can almost always walk in.

Melody’s Piano Bar, Upper East Side - a garden-level piano bar with music every night for a minimal charge. Enjoy signature cocktails and a range of friendly musicians who love to interact with their audience by taking requests, chatting between songs, or giving cocktail recommendations. With this relaxed relationship combined with excellent service, low light midcentury table lamps, and eccentric palm tree wallpaper, Melody’s revives the old-school Lexington Avenue piano lounge. You’ll sit among couples on third dates finally getting to know each other and members of the shrinking Upper East Side club of those who still wear the gentleman’s uniform. Arrive early to strike up a chat with the musicians before they take their places. Reservation recommended but not necessary.

The Rum House (above), Midtown - aptly named, this post-theater jazz joint is intimate and dimly lit, the perfect atmosphere for the well-dressed wandering midtown after their play lets out. Small snacks paired with aged rums mix well with a surprisingly high tier of contemporary and vintage jazz late into the night, all free of cover charge. Close quarters means you can engage directly with the music up front or retreat to a booth in the back and let the liquor do the talking. Needless to say, this place is a lot of fun. Walk-in recommended, reservations available Wednesday through Saturday.

For tobacco and conversation

The Carnegie Club, Midtown - an obligatory inclusion on this list, home to Sinatra Saturdays and the standard for cigar lounge service. While I admit the cigar and whiskey selections are not the best in the city, the atmosphere and history of the club more than makes amends. You’ll sit among 18^th century bookcases filled to the brim with books worthy of a Sotheby’s auction, in plush seating that harkens back to the day of Ol’ Blue Eyes. While I can’t claim to know any, a source tells me this is a regular spot for members of The University Club. The Carnegie Club is a great place to bring a visiting friend or to stop by if you’re in town for the weekend, as it sits right in the heart of midtown close to some other Carnegie-named New York institutions. Reservation recommended.

Hudson Bar and Books (above), West Village - an old school, smoky, and intimate club with an enforced dress code. Another place with excellent service, bartenders in ties, and a Bond film always on in the back. Enjoy indoor or outdoor smoking with some of the more reasonable tobacco prices in the city. This is my regular spot for an after-work smoke, and I’ve encountered everyone from New York Giants linebackers to startup founders in town for meetings with NASA. Reservation recommended Friday through Saturday, all other times feel free to walk in.

Davidoff of Geneva, Williamsburg - just a block down from Peter Luger, enjoy some of the finest cigars available to the U.S. in a refined but unstuffy atmosphere. My well-dressed friends tell me the iconic steakhouse down the street means you’ll encounter many businessmen coming to celebrate the brokering of deals at Peter Luger, so bring a resume. With a large humidor and BYOB lounge in the back, Davidoff’s staff will guide you to a pairing with whatever your booze of choice is for the evening. Grab a unique ashtray or S.T. DuPont on your way out. Walk in or reserve for the lounge!

For food and revelations

Theodora, Fort Greene - the best meal I’ve ever had. Mediterranean-inspired small plates with a few surprises, coupled with excellent service and a trendier ambiance, make for a great evening you won’t forget. Here, you’re falling in with the more trendy, Brooklyn crowd, but don’t let that keep you away; this is a perfect place to bring a significant other or a few close friends. Get the snapper and the sourdough, don’t skip dessert. Check for available reservations at least 3 weeks in advance, call if within a week to ask about cancellations.

The Polo Bar (above), Midtown - If you can get in, I have never seen a restaurant better curated and outfitted than Ralph Lauren’s masterpiece. There may have never been, nor may there ever be, more mahogany in one dining room than here. Everything from the chair you sit on to the glass you drink from feels sturdy and authentic, backed up by the extremely knowledgeable staff that guide you through all the nuances of the dining experience. You’ll find quite the range of customers here due to the iconic status of the restaurant, however if you need some outfit inspiration, look no further than a room full of Ralph mannequins. If you’re a networking machine, the time to strike a conversation with those who have regular access to the restaurant is while having a drink in the bar before going down to the dining room. Focus your full attention on the dining experience while seated. Indulge here: dress up, get starters, salad, mains, dessert and coffee. The Tuxedo martini is my favorite cocktail of all time.

Gatsby’s Landing, Midtown - much easier to get into than the above two options, a roaring 20s interior with plush seating and decent service. The raw bar is fantastic, as is the duck; pair either with champagne or an espresso martini once finished. You’ll see more of a tourist crowd here, but the proximity to the theaters gives you a more dressed-up clientele and a chance to meet someone like a Georgia menswear manufacturer on layover from a factory visit in Vietnam, still hurting from his $28 souvenir cup of wine at the theater.

For beer and anything fried

The Craic (below), Williamsburg - a longtime favorite of mine. In this basement-level pub, you won’t see so many Ivy guys, but you’ll be mingling with the younger finance types who are more into Rolex and Omega than J. Press and Brooks Brothers. Networking opportunities aside, the Guinness is the best in Brooklyn if not the whole metro area; food includes Irish pub classics and American bar snacks, perfect for a happy hour.

The Dead Rabbit, Financial District – An Irish pub in a historic area. Go upstairs for a fantastic European beer selection, fried chicken, fish and chips, and an all-day Irish breakfast if that’s your thing. While not crowded, the signature cramped architecture of downtown creates a cozy atmosphere that emulates a pub from the UK. However, this is one of the few places that gets very lively on Friday and Saturday nights in the Financial District. Much like at the Craic, you’ll mingle with 70-hour work week associates hoping to climb the ladder faster than you; great people to be friends with, in case they do.

For rare finds and gentleman’s goods

Zaidi’s, Chinatown - look no further for all your smoking needs. Inside, you’ll meet Sammy, who is endlessly passionate about vintage lighters in all their forms. Whether you’re shopping for a 1920s table lighter or have one that needs fixing, they’ll take great care of you.

Theo’s Haberdashery (above), NoHo - tucked away off the 8th Street NRW stop, Theo’s boasts an extremely curated collection of 1930s through 1970s Americana, but that’s only part of the reason to visit. Inside, you’ll find two large case lines of carefully selected vintage watches ranging from the 1920s to the 1990s, made by every significant brand throughout the period. The owner is wonderful and knowledgeable about everything in his shop, including the selection of private-label cigars rolled by hand in NYC.

Fine and Dandy, Hell’s Kitchen - two stores that share an address, Matt on the left side carries new fine gentleman’s accessories like cufflinks, ascots, ties, pocket squares, and Royall products; I get all my pocket squares from him. On the other side, his partner Enrique runs a treasure hunt of a vintage Americana store. You can strike up a conversation easily with both on their respective specialties and leave more stylish than you came.