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.
Cargo Shorts Are Back: Why Function-First Is Having a Moment
By Aalyah De Leon
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Last summer, I found myself constantly frustrated with the rotation of my shorts.
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Every time I left the apartment, I'd end up doing this awkward juggling act: phone in one pocket, keys in another, wallet somewhere else, and inevitably, something would fall out or create weird bulges that ruined the clean lines I was going for.
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Then I noticed something happening around the city. In SoHo coffee shops, at Brooklyn galleries, on Manhattan Street corners, young guys who knew what they were doing were wearing cargo shorts.
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But these weren't the versions I remembered from years past. These were sleek, well-fitted pieces that somehow managed to look both functional and intentional.
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The lightbulb moment came during a gallery opening in Chelsea. This photographer I follow on Instagram showed up in perfectly tailored olive cargo shorts, a linen button-up, and vintage Adidas.
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He looked effortlessly put-together while having enough pocket space for his phone, keys, film canisters, and whatever else his creative life demanded. Meanwhile, I was doing the awkward pocket pat-down dance, trying to figure out where I'd put my MetroCard.
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That's when I realized cargo shorts weren't just coming back, they were being completely reimagined for a generation that values both style and functionality.
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Modern cargo shorts success stories generally break into two approaches: those mastering "refined utility" (pieces that maintain cargo functionality while applying contemporary tailoring standards) and those embracing "street-ready function" (cuts and styling that draw from skate culture, streetwear, and the current obsession with technical wear).
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Here's what separates the cargo shorts that work from the ones that don't:
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The refined utility approach treats cargo shorts like any other quality garment that happens to have extra pockets.
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The key details matter: a 7-inch inseam that hits above the knee, a slim-but-not-skinny fit through the thigh, and pockets that lay flat instead of bulging out like tumor growths.
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The fabric quality is crucial; you want something with structure that holds its shape, not flimsy material that looks cheap after one wash.
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I watched my roommate completely upgrade his weekend style with one pair of well-cut khaki cargos from a contemporary brand.
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Instead of his usual rotation of athletic shorts that made him look like he was perpetually heading to or from the gym, he had something that worked for brunch in Park Slope, afternoon museum visits, and casual drinks afterward. Same comfort level, infinitely more versatile
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I've seen too many guys fail spectacularly at this approach because they grabbed the biggest, most pocket-heavy pair they could find without considering proportions or styling. Cargo shorts should enhance your silhouette, not hide it under layers of fabric and hardware.
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The breakthrough happens when you stop thinking about cargo shorts as a fashion statement and start seeing them as a practical solution. Good cargo shorts solve real urban problems: you can carry your essentials without a bag, your phone doesn't fall out when you sit down, and you have space for life's random necessities without looking like you're wearing a utility vest.
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But here's what matters is understanding how to choose and style cargo shorts to build genuine fashion confidence.
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When you can take a piece that most people dismiss as unfashionable, identify what makes it work in contemporary contexts, and integrate it.
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More importantly, you develop the ability to prioritize your actual lifestyle needs over arbitrary fashion rules.
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Maybe you need pockets for your creative tools, your city essentials, or just because you're tired of carrying a bag everywhere.
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Once you stop apologizing for practical choices and start making them with intention, your entire approach to getting dressed becomes more authentic and confident. The best part?
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When you nail cargo shorts, you realize the same principles apply to every other "controversial" trend.
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When function meets fashion, embrace the intersection. Make something practical of it.
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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