How to Craft the Perfect Casual Weekend Wardrobe

Aleks Cvetkovic
·3 min read

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Clothes generally serve a purpose (besides the basics of warmth and covering the old birthday suit, that is). A sharp jacket and tie for your C-suite business meeting. For a flight, sportswear’s relaxed layers will keep you cool and comfortable while on the move. For a workout, shorts and a tee in breathable fabrics allow you to pivot or sprint without restriction. What, though, should you do on the weekends when there’s no one to impress, no pickup game and zero specific objectives on the docket?

There’s no easy answer. A man’s casual wardrobe is the toughest to get right, because it’s entirely self-reflective. It has to be comfortable, express who you are and ensure you look reasonably well put-together all at the same time.

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With this trio of goals in mind, I’ve gravitated toward preppy menswear. As a freelance writer, I don’t need to wear a suit to work every day, and Ivy League style has sat comfortably across the “smart versus casual” aisle for decades. Mark Cho, cofounder of the Armoury, calls preppy menswear “tailored normcore,” and it’s that aspect which makes a navy blazer, oxford shirt or gray flannels so useful, whether you dress them up for work or down outside the office.

Not that I’m suggesting you wear only preppy clothes when off duty. My point is there are no dress codes or guidelines to follow on the weekends, so you have to develop your own framework. Preppy menswear happens to be mine, but streetwear also has a role to play in developing your casual style; it’s just another take on normcore, and dozens of high-end and artisan designers are making smart-looking sneakers and sweats right now. There’s something appealing about pairing an unstructured blazer and jersey sweater with chinos and clean white sneakers. The combo hits all the notes a laid-back wardrobe should: It’s practical, stylish and not too showy. And while it might have its antecedent in the 1950s, there’s still something very up-to-the-minute about it, too.

The secret to a versatile wardrobe is to steer clear of statement pieces, which tend to date after a season or two. A bright orange jacket might seem like a good idea at the time, but you’ll get tired of trying to make it work within six months. Though it’s important to show some personality with your off-duty look, gimmicky items are a no-go. You should have fun—not wear it.

Instead, let yourself be charmed by a classic item, whether that means an Amié Leon Dore hoodie or a Ralph Lauren sport coat. A few flannel shirts, a casual jacket, some selvedge-denim jeans and a well-made gray jersey sweatshirt will take you a long way. There’s a real pleasure to be found in how such articles feel after you’ve spent five days trussed up in a suit and stiff oxfords. They are cozy and soothing, the sartorial equivalent of a frothy cappuccino on a cold Sunday morning.

That’s the real point. Casual clothing is for that time of the week when there’s no uniform, no rules. If you build a capsule of dependable, relaxed pieces that work together easily, you’ll feel good when you wear them. If the casual wardrobe has a purpose, it’s to let you be you.

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