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Smart casual: A how-to style guide for men

Be comfortable and look great

Man in business casual
Andrea Piacquadio / Pexels

The style of men is a tangled web of confusion, innovation, and maybe a little bit of apathy. It’s difficult for men to care about their wardrobes, thanks to the confusion that comes along with etiquette, trends, and the rules and guidelines you can sometimes break and sometimes rigidly follow. That is why The Manual exists: to navigate that frustration and help you find your best looks without pulling your hair out. Smart casual is another term that seems to meld two or more different looks into one confusing ball of threads. Luckily for you, it isn’t nearly as difficult as you think.

If you’re still trying to wrangle your personal style, you’ll appreciate this breakdown of how to assemble a versatile, classy wardrobe that will leave you comfortable and confident in any situation. If your eyes are darting back and forth between this screen and that invitation, you can stop freaking out because we’ve got a round-up of smart casual rules and recommendations to help you rock this look with confidence.

Smart casual vs. business casual

Man in smart casual at a bar
Alena Darmel / Pexels

The levels and designations between clothing styles have gotten confusing over the last few decades or so. It used to be that when you went to work, you wore a suit without question. When you were not on the clock, you went more casual. There was casual, and there was professional.

Ever since the world began to get more and more casual, the waters have been muddied. The ever-confusing business casual became the go-to for the office after the casualization of workwear. Now, the appearance of smart casual confuses even more guys. What is the difference between business casual and smart casual? The answer comes in the base look. Business casual is taking business professional and scaling it down, like losing the tie with the suit or replacing the suit with a sports coat. Smart casual is taking a casual look and elevating it with something dressier, like throwing a sport coat on over your casual top and denim.

To start out, you’ll need to stock up on clothes that are smart and stylish but neutral enough to combine with ease to fit any occasion. This list of staple smart casual pieces is a good place to start filling out your closet. If you already have some pieces that fit these descriptions, great! Hang on to those and add a few new ones to freshen up your look. If you open up your closet and find yourself in need of a full overhaul, keep these basics in mind while shopping for your new wardrobe.

On the top

Blazer with silver buttons
Muhammad Numan / Unsplash
  • Blazers, jackets and vests: A sharp blazer is a great investment if you’re aiming for a smart casual look. Choose a blazer that fits well and has a neutral color for maximum versatility. Denim jackets are great for those outfits that may lean a bit more casual, while leather and flannel are perfect ways to up the visual interest by adding texture and pattern.
  • Classic T-shirts and stylish sweatshirts: It may seem counterintuitive to add T-shirts to a swanky wardrobe, but a good-quality tee or sweatshirt can be a real powerhouse in a smart casual closet. You can dress up your tee by wearing it under a blazer or dress down your favorite trousers with a cozy sweatshirt.
  • Oxfords: It probably doesn’t come as much of a surprise that the classic button-up dress shirt fits into this style, but to really blend your oxfords with the rest of this look, choose a cool color and pop open the top button.
  • Grandfather collar shirts: Grandfather collar shirts are a great alternative when you feel like you’ve been playing it too safe with your traditional button-ups. The unique collar can be paired with chinos for work or slipped under a denim jacket for days off.
  • Sweaters: If you live in a place with a chilly winter season, you may be looking for ways to layer up and still look good. Well-fitting sweaters can be easily combined with other smart casual staples for a toastier style.
  • Knit shirts: Who doesn’t love a good neutral knit? Great news: you don’t have to give them up to go smart-casual. They pair well with classier pieces like chinos and more toned-down choices like slim denim.

On the bottom

man in black shirt and chinos
Gaspar Zaldo / Pexels
  • Chinos: Chinos are slim, smooth, smart, and classic. They fit right into any smart casual wardrobe.
  • Tapered or slim-fit jeans: Upping your fashion game sometimes means giving up your favorite weekend warriors — your jeans. Fear not — jeans are welcome in this style, so long as they are well-fitting and rip-free. To keep your look bold but balanced, choose darker colors like Navy or black, and steer clear of white-washed or faded jeans.
  • Shorts: You might have to sacrifice your board shorts, but you don’t need to sweat to stay stylish in the summer. Keep cool and keep confident with smart, clean-cut shorts for warm weather.

On your feet

  • Loafers: A nearly pure blend of comfort and class, loafers can be a perfect complement to a wide variety of smart casual outfits.
  • Brogues: Few things can compete with a classic brogue when it comes to footwear. Pair them with dark socks and let them speak for themselves, or add a pair of printed socks to dress them down when you’re out on the town.
  • Desert boots: These boots’ distinct but wearable look makes them perfect for pairing with a serious blazer or a comfortable knit.

Accessories

Man wearing watch
Luca Nardone / Pexels
  • Pocket squares: It takes only seconds to tuck it into the front of your jacket, but a well-chosen pocket square can light up any outfit.
  • Classy sunglasses: Leave those shutter shades at home and instead choose a pair with understated frames and transparent lenses to keep your look on point while catching some rays.
  • Casual ties: While a traditional suit and tie get-up is a bit too formal for a smart casual look, styles like patterned square ties, bow ties or ties tucked under a sweater or vest are great options for adding an interesting but appropriate accessory.
  • Watches and jewelry: A sleek watch or subtle wrist wrap can elevate a nearly perfect ensemble — just avoid overdoing it with loud colors or overpowering bling.

OK, so you’ve got your staples covered, but having a well-equipped closet does not a fashion statement make. To make the most of your versatile duds, you’ve got to combine them thoughtfully. Here are some tried-and-true tips for mastering the smart casual style.

Consider the circumstances

Man wearing white shirt and suit
LinkedIn Sales Solutions / Unsplash

The golden rule of smart casual is to know your audience. The whole idea is to strike a pleasing balance between two seemingly opposite styles, so it’s important that you tailor this balance to fit your activities, or you could end up crashing the party with an outfit that stands out in all the wrong ways. Are you heading off to totally crush that interview you’ve been anticipating for days?

While chill-friendly tees and slim denim might be great for a breezy weekend, try swapping them for a smarter, more polished Oxford-chino combo for professional settings. Add a dash of smart comfort by finishing the outfit with a pair of dressy loafers. If you’re heading out to celebrate the weekend with the guys, spice your style up by pairing dark jeans with a classic tee and bold blazer.

Strike a balance

If the key element of smart casual is to achieve a unique balance, then it stands to reason that you won’t be able to master the look without mastering that balance. Smart casual is a versatile style, but you always need to have a certain symbiosis in mind when planning your outfits. As a general rule of thumb, you should smarten up your bottom half if you’re going casual on the top, and vice versa. Dress those textured shirts up with a sleek pair of chinos and an oxford peeking over the collar. Chill out a crisp button-down with tapered denim and a pair of neutral boots.

Keep it subtle

The smart casual look is a combination of comfort and elegance, so you never want to look too “loud,” no matter the occasion. When stocking your wardrobe, stick with soft hues, subtle patterns, and plenty of solid colors. Neutral pieces can be dressed up or down to suit a variety of situations. Dress up a grandfather collar shirt with a well-fitting jacket, or throw it over some black denim and boots. For that bit of extra style, throw in a tweed jacket for texture or a bold watch to compliment your look.

Tailor, slim, and trim

Whether you’re dressing up for a party or dressing for downtime, smart casual is a cool, classy style, so your clothes should be well-fitting and never baggy. You want to look effortlessly dapper, not like you’re planning to spend the day binging on pizza and Netflix. Consider getting your best pieces tailored for the perfect fit, and when shopping, be sure to stick to styles that tend toward a slimmer fit. You don’t need to fill your closet with skinny jeans but opt for tapered or slim pants over baggy, frayed, or weathered denim.

Designer T-shirts have a very welcome place in the smart casual style, but steer clear of shirts with big, loud graphics or an oversized fit. Instead, choose well-made, understated shirts that look equally thoughtful with a blazer or denim jacket. Bulkier layers should be carefully chosen as well — a slim knit jumper is a perfect fit for the style, but your favorite oversized Christmas sweater certainly isn’t.

Now that you’re smart-casual savvy and armed with a shopping list, you’re ready to keep it classy and cool by mastering this trendy style. As you experiment with the smart casual look, you may branch out into bolder choices and more innovative combinations, but remember: When in doubt, it’s best to err on the side of smarter over more casual. After all, it’s better to be overdressed, as they say.

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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