A great suit is unlike anything else in your closet—timeless and elegant, certainly, but also difficult to get right. The process of choosing, buying, and caring for fine tailoring is often fraught with tough decisions, confusing jargon, and conflicting opinions. That’s why we’ve assembled an all-star roster of the world’s most knowledgeable menswear experts to definitively answer all of your sartorial questions. Welcome to GQ’s Ask a Tailor.

Tailors are mostly pretty agreeable folks. They’ll happily spend hours chatting with you about the perfect lapel roll or why a floating canvas is superior to a fused one. They’ll also help to steer you towards good sartorial choices, away from bad ones, and—if they’re really good at their job—make it seem like the whole thing was your idea all along.

If you want to make a traditional tailor roll their eyes, however, ask them to make you a skinny suit. They’ll probably do it (because it’s their job to give you what you want at the end of the day) but they will also silently shake their heads in dismay and perhaps cry a little inside. To understand tailors’ near-universal dislike for the definitive suit of the 2010s, we asked a few of the world’s most respected names in menswear to break it down for us.

Reason 1: Skinny suits have an expiration date

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A trim and tidy—but certainly not skinny—two-piece by Savile Row stalwart Huntsman.

An old-school craftsperson like NYC tailor Leonard Logsdail prides himself on making clothes his clients will wear for decades. A suit based on what’s currently fashionable, by comparison, has a much shorter shelf life, and he endeavors to impart this distinction to clients who come in asking for skinny suits. “Do you want to be wearing this suit in five years?” he poses. “If so, you’re going to look like you’re wearing a suit that’s five years old. Because by that time the fashions will have changed.”

At Drake’s, creative director Michael Hill is of the same camp. “Proportions evolve and change over time, but it’s not for us to follow that,” Hill says, noting that the tweed blazer he’s wearing is 15 years old and looks as rakish today as it did in 2009. “We’re trying to make a garment that’s going to last 20 years, and I think it’s a question of being confident about what works for you, rather than what works for the fashion houses.” Fashion, Hill concedes, is always going to be a significant element of menswear, but a suit—especially a suit you plan to wear for 15 years or more—should be part of a much longer view of your wardrobe, not just what looks good this season.

Reason 2: Skinny suits aren’t comfortable (or flattering) on a lot of bodies

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The classic silhouette of menswear expert Bruce Boyer’s double-breasted suit will stand the test of time.

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