Getting it Right: What Not to Do When Seeing a Tailor

Tailor Anthony Sinclair fits Sean Connery for one of the suits he will wear in the film 'From Russia With Love', 1963.
Tailor Anthony Sinclair fits Sean Connery for one of the suits he will wear in the film 'From Russia With Love', 1963. United Artists / Getty Images

The Council of Fashion Designers of America (CFDA) recently announced that menswear would get its first ever dedicated fashion week in New York this July, cleverly dubbed New York Fashion Week: Men's. It's a big deal in an institutional sense, but, as an announcement, it was the culmination of a decade-long, intense increase in general interest towards menswear — and specifically in tailoring. A perfect fit can eclipse most trends, but actually getting something customized, whether it's hemming a pair of pants or having a piece made completely from scratch — to measure or bespoke — is foreign to guys who have been living off the rack their whole lives. So we talked to a couple of New York's most renowned tailors about how you should go about getting that perfect fit.

1. Know What Your Tailor Does Best.
All tailors have a specialty, whether it be as broad as Italian or English, or something as specific as, say, a cropped Thom Browne suit. Amber Doyle, co-founder of Against Nature NYC, specializes in "a modern and somewhat rock-and-roll approach to the traditional Savile Row suit. Our silhouette is sharp, clean, and trim fitted."

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2. But Don’t Be Afraid to Ask for Something Else
Just as Against Nature specializes in its look, other tailors are more willing to work outside their comfort zone. Daniel Lewis, co-founder of Brooklyn Tailors, says, "I love getting the customers who come in and say, 'I really love what you do — your suits look great on other people, but it's just not me.' We figure out exactly what will make those guys comfortable." If a tailor like Lewis (and his wife and fellow founder, Brenna) is capable of creating well-made, distinctive suits of a certain style, they'll likely be able to make something out of their box.

3. Buy A Suit That Fits
This seems obvious, but hear us out: A lot of men are insecure about something, whether it's their gut, their height, or the slope of their shoulders. We all think we've discovered how to hide what we dislike about ourselves, but chances are we're doing ourselves a disservice. "Shorter guys tend to want longer jackets because they think it will make them look taller, when in fact the opposite is true," Lewis explains. "Heavier guys tend to want baggier suits because they think it will make them look slimmer, which is also not the case. We've fit enough people and body types to know what works and what doesn't." So, once again, listen to your tailor, even if you aren't comfortable at first.

4. Don't Get Too Crazy For Your First Suit
Suits as on-trend as they might be are, at their most basic, staples. "If someone were to come in to have their first suit made, I would suggest a modern fit that is not too traditional or trendy. It should be in a classic color, like gray or navy," Lewis says. "You'll get the most bang for your buck that way." Similarly, avoid picking black for a first suit.

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5. You Can Find Quality Suits Buying Off the Rack
A custom suit is a beautiful thing, but many men can look just as good in a sharply made suit or shirt that's pulled off the rack. "We always tell customers to go to our store first and try on our off-the-rack suits. If those fit great and you love the style, then there's no reason to go custom," Lewis says. "We don't want customers paying extra money and taking more time if it's not necessary."

6. Don't Worry About Growing Out of Your Custom Suit
One of the biggest fears with ordering something completely fitted is that we all gain and lose weight over time. Why spend hundreds or thousands of dollars on a suit if you can't wear it after a few months of stress-eating? "Suits can absolutely be altered should your weight fluctuate or stylistic preferences change," Lewis says. Still, don't go overboard: We have an allowance of one inch on all seams, which allows jackets and pants to be let out one full size.

A few more quick rules:
Remember that these tailors are professionals, so canceled appointments are wasted time and money, throwing a wrench into these specialized business's schedules. Also, outside alterations are mostly not welcome, but bringing back previously purchased items is. But don’t be afraid. This newest breed of specialized tailors loves what they do, and they want you enjoy it, too. Doyle, when asked if there’s anything customers do that annoy her, laughed and said, "There are always things that can be difficult with any fitting or client, but ultimately I enjoy what I do and most of our clients are a pleasure to work with."

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