Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
Why Denim Shorts Are Fashion's Unexpected Comeback
By Aalyah De Leon
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I'll admit it, two years ago, if you'd told me I'd be writing about jorts as a legitimate menswear option, I would've laughed.
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Like most guys, I associated denim shorts with middle school awkwardness and dad barbecues.
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Then I started noticing something on the streets of Brooklyn and downtown Manhattan: young creatives, stylish guys who knew what they were doing, rocking jorts with genuine confidence.
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Modern jorts success stories generally fall into two camps: those nailing "grown-up construction" (pieces that treat denim shorts with the same respect as quality trousers, focusing on fit and proportion) and those embracing "streetwear authenticity" (cuts and styling that draw from skate culture, hip-hop, and contemporary youth movements without looking like costumes).
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Here's what I've learned from watching guys get jorts right and very, very wrong:
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The grown-up construction approach is all about treating jorts like any other quality garment.
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The magic happens in the details: a 7–8-inch inseam that hits just above the knee, a fit that's relaxed but not baggy, and a wash that looks intentional rather than accidental.
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These aren't the cargo-pocket monsters your dad wore to wash the car; they're thoughtfully designed pieces that happen to be made from denim.
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I watched a friend transform his summer wardrobe with one pair of well-fitted dark jorts.
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Suddenly, his weekend uniform of beat-up khaki shorts and random t-shirts evolved into something that looked considered.
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Same comfort level, completely different impact. The key was understanding that jorts could be a foundation piece, not just a throwaway casual option.
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The streetwear authenticity route is trickier but potentially more rewarding.
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This is where you see wider cuts, unique washes, and proportions that reference '90s hip-hop or skate culture.
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But here's the catch: it only works if it genuinely reflects your style, not if you're trying to cosplay as someone younger.
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I've seen too many guys fail at this approach because they grabbed whatever jorts they saw on Instagram without considering whether it matched their actual lifestyle.
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A 35-year-old finance bro wearing oversized baggy jorts looks like he's having a midlife crisis, not a style moment.
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The breakthrough happens when you stop thinking about jorts as a trend and start seeing them as a tool.
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Good jorts solve real problems: they're more durable than most shorts, they get better with age instead of falling apart, and they offer a casual authenticity that chinos can't match.
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When you're grabbing coffee in the Village, exploring a street fair, or hanging out at a friend's backyard gathering, quality jorts just work.
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More importantly, understanding how to choose and style jorts builds the kind of fashion confidence that translates to every other clothing decision.
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When you can look at a piece that most people write off as unstylish, identify what makes it work or fail, and integrate it successfully into your wardrobe, you've developed real style intuition.
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The best part? Once you crack the Jorts code, you realize the same principles apply to every other "questionable" piece you've been avoiding.
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Bucket hats, colored denim, graphic tees, suddenly, you have the tools to evaluate these pieces on their own merits rather than dismissing them based on outdated assumptions.
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When comfort meets confidence, own it completely. Make something bold of it.
Heritage in amateur hands has the shelf life of sushi at a gas station.
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Too much reverence and you're cosplaying your grandfather's funeral.
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Too little and you're just another banker in regulation navy.
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But between Princeton's manicured lawns and Yorkshire's unforgiving moors, something has shifted—menswear is learning to fight with style again.
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The Ivy Insurrection
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Prep died the day it became about pedigree instead of attitude. Today's iteration isn't concerned with where daddy went to school—it's about weaponizing a cricket sweater for maximum disruption, whether you're closing deals or starting revolutions.
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The Japanese, naturally, cracked the code first. While Americans were still genuflecting at country club altars, Beams Plus treated Ivy classics like source material for something better.
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Rugby shirts blown up to statement proportions. Blazers cut with the radical notion that human shoulders might exist. Cricket sweaters liberated from their sporting pretensions and reimagined as power moves.
British menswear was always about survival—Scottish winters, boarding school food, navigating "smart casual" dress codes without losing your mind.
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What's changed is that survival gear has evolved beyond function into something approaching art. Waxed cotton now gets tailored like evening wear. Corduroy explodes into technicolor rebellion.
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Harris Tweed quietly incorporates NASA-grade technology while maintaining its 1953 poker face.
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This is combat gear for battles fought in glass towers and comment sections.
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Kartik Kumra embroiders intricate patterns onto traditional silhouettes like he's decorating armor for wars fought entirely in three-Michelin restaurants.
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Barbour, bless’em, has embraced collaboration culture, letting insurgent designers reimagine their heritage pieces—resulting in jackets equally at home shooting grouse on Yorkshire moors or mixing cocktails on Williamsburg rooftops.
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Even Ralph Lauren has noticed the wind direction, deploying their considerable resources toward cricket sweaters and rugby shirts with their usual impeccable timing.
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The Hybrid Advantage
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The revolution isn't about choosing camps—it's about refusing the choice entirely. Cricket sweaters under waxed coats. Rugby shirts with Harris Tweed. Loafers engineered to survive actual apocalypse scenarios.
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This is menswear's punk moment: seize the establishment's own weapons and turn them against everything they represent.
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Your grandfather's sporting kit, your father's business uniform—all fodder for creative destruction.
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Five years ago, "quiet luxury" meant telegraphing wealth through codes only the initiated could decipher.
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The new game is louder—not flashy, but uncompromising.
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Clothes that look lived-in because they're designed for living.
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The Performance Paradox
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Ownership isn't about acquisition—it's about convincing the world these pieces have always been yours. Even if you acquired them moments ago from a boutique where the staff earn more than your accountant.
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Everything must suggest history without theatricality.
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Your cricket sweater should imply athletic prowess, even if your coordination peaks at opening wine bottles.
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Your tweed should look weather-tested, not showroom-fresh.
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That sound you hear? Our old friend sprezzatura is in the wings, getting ready for the big aria.
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Forward Evolution
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Expect technology to keep undermining traditionalists—tweed that repels water like goose down, corduroy with athleisure stretch, dress shoes built on hiking boot foundations.
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Expect cuts that ignore gender conventions, making old-school tailors cry into their beer.
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Heritage used to mean conforming to the past.
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Now it means conquering the future.
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The Hit List: 10 Pieces That Matter
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The Embroidered Cricket Sweater (Ralph Lauren) ​Because subtlety is for people who don't have anything interesting to say
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The Engineered Waxed Jacket(Barbour x Engineered Garments)Pre-weathered, because pristine outdoor gear is a tell
Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
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