So You Bought a Pair of Levi’s. Now What? How to Wear Blue Jeans Without Looking Basic

Red alert! (Literally.) Timothee Chalamet just wore a red halter top on the red carpet of the Venice Film Festival. Of course, it was Hader Ackerman. And of course, it broke the internet. But before you go trying to replicate this at Clandestino (but if you’re set on getting the look: scour eBay or Depop for “satin halter tops” — you’re welcome), don’t get intimidated. You can still dress like yourself while dressing to impress. All it takes is a pair of Levi's Jeans.

The state of men’s fashion is ambiguous at best. It used to be simple. Tucked in shirt, shined shoes, and combed hair. Now, none of the rules apply.

Timothee Chalamet in VeniceHe ate ... but at what costvia Shutterstock

Brad Pitt has been showing up on red carpets in neon and sneakers. Gatekeepers of men’s fashion are holding tête-à-têtes in Dimes Square, arguing about whether Sambas are dead or not. And everyone seems to be wearing Crocs or New Balances. You might think this chaotic energy should be fun and playful. But, honestly, it’s confusing. With this abundance of options, how is anyone supposed to know how to dress?

And here’s the thing: how you dress matters more than ever. The age of TikTok microtrends is not just a major influence on women’s fashion. How bout that indecipherable world of Avant basic, old money/dark academia, or whatever, and then there’s everything in between. But these microtrends are changing how we think about fashion. Expressing yourself through clothes is an art. And the world’s raising the stakes.

Everywhere you look, someone’s showing off their fit pics and posting about how to elevate your style. Who knew there were so many ways to wear tee shirts? And so many are wrong. And every guy you see on the street these days is pairing their 70s-inspired handlebar mustache with ironic trucker hats and trying not to look like an asshole. And you are here, confused.

Then you have male celebrities throwing fits we can’t hope to keep up with. Comparing yourself with any celebrity is a losing game — especially loser celebs. But suddenly, you’re scrolling through GQ’s Instagram and saving outfit pictures of Joe Jonas, Jonah Hill, and Oscar Issac all in the same breath. This is what it’s come to in this bewildering but exhilarating race to look decent.

Despite the likes of Harry Styles, Timothee Chalamet, and Lil Nas X boosting the game on every red carpet, there’s still hope for you. And, believe it or not, there’s no need to disavow the basics in pursuit of the ephemeral “good style.”

The basics: a white tee (a la Carmy from The Bear) and a pair of blue jeans. Levis, of course.

Let’s face it: Levi’s jeans are truly one of the greatest American inventions. A fine pair of jeans is a staple in any wardrobe — no matter how much or how little you care about fashion. No matter where you fall on the fashion-obsessed spectrum, there’s a right and a wrong way to wear jeans.

The wrong way: anything uncomfortable. That’s right! Contrary to popular opinion, jeans should actually be comfortable. My personal favorites are essentially sweatpants — roomy, worn in, and suitable for any activity. I wear them on international flights, long car rides, and nights out alike. And of course, they’re my Levi’s.

Levi’s are a classic for a reason: they only get better with age. How they look depends on how you style them. But their quality brings together any fit. So don’t overthink it. Buy a pair of Levi’s.

Amongst all the outrageous street style and red carpet ensembles your faves are rocking, there’s remains a place in this sartorial humdrum for jeans. Don’t believe it? Here are some fits that prove there’s a style for everyone — and provide inspo about which Levi’s to buy:

All products featured are independently selected by our editors. Things you buy through our links may earn us a commission.

Elliot Page, Straight Cut 501

If any look is both classic and cool, it’s this one. Elliot Page is proof. These days, a pair of jeans and a blazer is appropriate attire for pretty much anywhere — the airport, the office, and dinner out. Take this look from slouchy to sharp by making sure your jeans are the right cut. Go for the classic Levi’s 501, and you won’t fail.

Ramy, Levi's 531 Distressed Slim Fit Jeans

Make your classic fit a little more relaxed with slouchy slim cut jeans. Wear these anywhere to look like you know what you're doing. Ramy Youssef is known for his complexity and relatability in his hit Hulu show, Ramy, so take his cues in fashion, too.

Bonus: get a distressed pair to add some edge to your look. One little rip goes a long way.

Luka Sabbat, Canadian Tuxedo

The only thing better than denim is double denim. Bring back the Canadian tuxedo for an instantly intriguing but effortlessly bold look. Pair your Levis jeans with a Levi’s denim jacket. Whether you choose the same wash or mix and match different colors, that’s up to you.

Nico Hiraga, Slouchy Denim

No thoughts, just vibes. Slouchy denim is the new sweatpants — just slightly more put together and effortlessly cool.

Harry Styles, 70s Boot Cut

And, last, but not least, Harry Styles popped up in Venice in a grape-colored coat and bootcut denim. That was the last peaceful moment he had in Venice … sorry to that man. Sure, his fit was entirely Gucci, but a good pair of flared Levis can completely level up your game. If you want to take a risk and engage in Harry-esque fashion trends, dip your toes in here.

All products featured are independently selected by our editors. Things you buy through our links may earn us a commission.

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