A Men’s Guide to Dressing Casual Yet Classy

Studies show that men who dress well are perceived as sexier and more successful than their schlubbier brothers. But do you know how to carry off a casual look?

In many ways, dressing casually is harder than dressing formally. In formal situations, your look is already defined — wear a suit, and you’ll look good. In informal situations, there are a whole host of other questions.

Is the best men’s casual style one that incorporates T-shirts or polos? Jeans or chinos?

You’re in luck because we’re here to help with our style expertise and generous hearts.

Want to cut through the jargon and know what classy casual outfits for guys will really make your style pop? Then read on fellows young and old, and discover the best casual looks for men.

T-Shirts and Jeans

The classic pairing. These two go together like peanut butter and jelly. When it comes to casual style for men, this is the easiest look to pull off.

There are some fashion faux-pas that you need to avoid, however.

When you’re choosing your T-shirt, look for:

  • Strong, clean designs. Throw your old slogan tees in the trash, and invest in a clean, classic-looking tee. With t-shirt brands like RVCA, Jasper Holland and Grunt Style making headway in the men’s casual fashion world, there is obviously a demand from the adult male market.

  • Solid-color T-shirts are your friends. A plain white shirt works with any casual look for guys, whether under a leather jacket for that fifties look, or a cardigan as part of a cozy, contemporary style.

  • Unless you’re going for a muscle fit, T-shirts shouldn’t be too tight or too baggy. Sleeves should end halfway to your elbow, with less than an inch of fabric to pinch.

When choosing jeans, bear in mind:

  • Fit. Avoid skinny jeans if you’re a larger guy, as nothing ruins men’s casual style like jeans that look as if they’re about to rip. If you’re a larger man, go for straight-leg or tapered jeans.

  • Avoid bootcut jeans like the plague. The only reason to ever wear them is as part of a work outfit.

  • They should be tight enough at the waist that you could wear them without a belt. They should end naturally around the ankle, so they do not cover your shoes.

Both jeans and tees are versatile weapons in a man’s wardrobe. Either can be paired with almost anything else on this list to complete casual looks for guys.

Polo Shirts

A slightly preppier cousin to the T-shirt, Polo shirts can help give you a sporty style.

You should choose a polo shirt based on your body type. If you’re slighter, look for one made of Jersey, while heavier fabrics are best for heavier guys. The sleeves should end at the bicep if you’re muscular, just below if you’re not.

A polo shirt paired with jeans is one rung above a T-shirt in terms of formality.

Casual Shirts

A casual button-up is noticeably more formal than a T-shirt, and owning a good selection of button-ups is key to casual style for men.

If you’re going on a coffee date or meeting friends at the bar, a casual shirt will separate you from the crowd. In summer, look for short-sleeved shirts, in white or pastel colors.

In winter, plaid flannel shirts are a timeless look. Their association with Seattle grunge has lent them a laid-back vibe, and heavier fabrics will keep you warm.

If wearing chinos, a denim shirt is another good option. These can be worn all year round. Wearing a denim shirt with jeans is a no-go.


Chinos are some of my favorite trousers. Made of cotton, they’re ideal for all but the harshest of weather and can go with everything. They form the backbone of truly classy casual outfits for guys.

Look for Chinos in khaki, navy blue, and stone. If you’re feeling bold, a pair of burgundy or teal chinos can add beautiful color to your outfit. Finally, a pair of white chinos, cuffed at the ankle, is a superb summer look.

If you want to step things up to smart-casual, add a blazer (of a different shade to your chinos), and you’re instantly 100 percent more stylish.

Chinos should fit like jeans, with a waist slightly lower than more formal pants. They should be snug to your thighs without being tight, with no more than 1.5 inches of pinchable fabric.

Once again, unless you’re thin, avoid skinny fit chinos. Opt for a tapered or regular fit instead.

Cardigans and Sweaters

When choosing knitwear for the colder months, choose colors that complement your trousers. Cardigans should also coordinate with any shirts you’re going to wear underneath them.

All colors can work, but avoid any patterns that are too bold. Nothing ruins men’s casual fashion like looking as though you’re wearing a Christmas sweater in October.

Merino wool sweaters are soft and warm enough for winters in many parts of the country. If you’re looking for heavier wool, cashmere is the very best but is expensive. Donegal wool is heavy, warm, and more affordable.


Sneakers are the perennial favorite as part of men’s casual style. We’d recommend sticking to sneakers that are mainly white or black, with a few bright colors. We’d especially recommend Nike Killshot 2s and Addidas Sambas.

For the colder months, when the ice starts appearing on pavements, a pair of casual boots is a must. Timberland boots are classics for a reason: they’re warm, grippy, and hardwearing.

If you want something different, consider buying a pair of Dr. Martens. These aren’t as grippy, but they’re hardwearing and have a punk/rocker look that’s very eye-catching.

Final Rules of Classy Casual Outfits For Guys

When you’re assembling a casual style, the most important thing is for your clothes to look laid-back. They should look like something you’d wear to a bar, not something you’d wear to a job interview.

When it comes to classy casual outfits for guys, as with all fashion, confidence is key. Buy clothes that you love and that make you happy, and walk tall while wearing them. Know what you can and can’t pull off, and go out and rock it!

Got any questions you’d like answered, or any feedback for us? Then get in touch with us via email!

About RJ Frometa

Head Honcho, Editor in Chief and writer here on VENTS. I don't like walking on the beach, but I love playing the guitar and geeking out about music. I am also a movie maniac and 6 hours sleeper.

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One comment

  1. Nice piece. I like the advice about solid colours and clean designs particularly as we get older as it is definitely better to avoid ‘shouting out’ after 30 (in my opinion)! One thing I would recommend is to avoid showy logos as it takes away somewhat from a relaxed look.

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