How to Wear Overalls: A Helpful Guide

We’re going to assume you weren’t alive in the 1700's, but if you were, you would have seen the birth of the great, utilitarian overalls. Also called coveralls by old-timey weirdos, overalls have evolved from their status as a symbol for the rising farmer class during The Great Depression, to the favored style of skaters, glam rockers and Tupac alike.

We may no longer be in a peak overall era—that would have most recently been in the 1990's. But considering how much that decade has influenced a new generation of tastemakers, you don't have to go to Oshkosh B'Gosh to catch overalls in action right now. Interested? Here’s what you need to know about how to wear overalls today.

We get it, you like your jeans on the slimmer side. That's understandable, considering that most dudes aren't afraid to go with tailored pants in order to create a streamlined silhouette. But when it comes to overalls, you should throw that thought process out the window. Overalls were designed to be worn by farmers or outdoorsmen with boots. We're not saying you should go full JNCO, but we're not recommending that you opt for anything remotely “European cut” either. Oh, and avoid short-cut overalls…rompers are a no-go for all grown-ass men.

While you're trying to tap into the overalls trend, it's a safe bet that you're trying to look a little more put together than a rancher who just came in from the pasture. For something that goes over your entire frame, it’s important to be smart about what goes under your overalls. Unless you cop all your ‘fits at Tractor Supply Company, avoid anything that crosses into country-Western territory—especially a full-on flannel shirt. We recommend keeping things simplified with a solid T-shirt or one with a subtle graphic. For a skate-centric vibe, a hoodie is another clutch choice. If shooting for a retro, “fresh of the Hilfiger runway” look, you can pair them with a rugby shirt. But, in general, a collared shirt with overalls is a blunder. Don't try to dress up overalls with a tie or anything remotely formalwear; that's a mixed-message that's just not going to translate…that is, unless you’re scoring dates at the country fair. Speaking of, before we forget, never go shirtless. Hillbilly Jim is hardly the style icon you should be emulating.

The '90s were all about wearing clothing in unconventional ways (Kriss Kross anyone?), and coveralls weren't exempt. While most buckled both straps over their shoulders, it was entirely on point to keep one strap down and unbuckled. Sure, that adds a relaxed vibe to the piece, but wearing overalls today is all about keeping things polished. It's about balance; overalls are naturally slouchy, and creating an even more unhinged look won't be doing you any more favors. Besides, you don't need to appear like a wayward kindergarten student while you're making a single strapped statement. When it comes to overalls, make sure to buckle up twice—or not at all, as demonstrated by A$AP Rocky’s collab with GUESS, which includes a pair meant to be worn with both straps down.

Brands like Dickies, Ben Davis, and Carhartt have been making overalls for decades, and there's a good reason for it. They're durable, they're solid, and they're true to the workman roots of the original garment. Same goes for the lightwash classics that saw love from the likes of Ralph Lauren, Levi's and GUESS. On either side of the spectrum, they embody both what overalls initially were, and the streetwear style that came to popularity in the '90s. Hey, when Tupac, TLC, Aaliyah, and Will Smith wore overalls, there's a good reason why they kept it to simple denim blues. Black, brown duck, or stonewashed blue—these will be the most versatile and easiest colors to test drive the trend. But having said that…

You can wear patterned overalls. Yes, patterned overalls are one hell of a style risk, and you could end up looking like a mix between Zubaz and Screech from Saved by the Bell, so you're better off keeping colors and patterns to a minimum. But, it's certainly possible. History has its own versions of patterned overalls, with railroad conductors in stripes that are about as American as you can get. But there are plenty of contemporary designers, like Astrid Andersen, who are willing to cross up coveralls with a variety of different patterns and prints—tradition be damned. Less is always going to be more if you’re not totally down to take a fashion risk, so steer clear of rocking a patterned shirt with your overalls, regardless of color. That’s something that only the Fresh Prince could get away with.