Dress Casually Like You Mean It

Dressing casually for a man may be more complicated than it seems. A smart casual look is intentional and takes forethought, and may even be more complicated than dressing up for a night on the town. “Smart casual” means you look like you’re in charge, but too cool for a necktie.

Going out to a five-star restaurant and then the theater? Put on a well-tailored suit, a white or light blue shirt with French cuffs, a colorful tie (but not too playful!), a white folded pocket square, and a pair of Oxfords, and you’re set. Casual, on the other hand, is poorly defined, and it’s far too easy to cross over from casual, to just plain sloppy if you’re not careful. Pants that are too long and trail the ground, or worse yet, pajama pants, aren’t casual, they are sloppy. Contrary to what your younger self may have believed, “casual” does not equal “I don’t care what I look like.” Here are a few “casual” no-no’s:

  • Don’t try to look younger than you really are. If you are north of 40 years old, the graphic tees, skinny jeans, and baseball cap worn backwards just makes you look like a man-child.
  • Jeans? Yes. But keep it simple and make sure they fit. Huge logos, overly baggy jeans, ripped jeans and sagging jeans that leave your underwear showing are a whole different type of casual, and that’s not the intentional “smart casual” look you want.
  • Don’t try to be Mark Zuckerberg. He’s famous for doing a lot of things very well, but dressing isn’t one of them. He can get away with wearing the same jeans-and-hoodie combination every day because he’s fabulously wealthy. You can’t.

Casual shoes tie it together

This is a big one, and that intentional casual look you’re going for will be completely ruined when you’re wearing your ten-year-old Walmart sneakers. You can leave the shiny black Oxfords for more formal occasions, but striking a balance in footwear is key, and this is what ties together the entire outfit. Keep in mind too, that pants that fit – and don’t hang all the way to the floor – will showcase those new casual kicks even better.

A great pair of sneakers may be just the thing, but a good casual wardrobe will mix it up a little with some comfortable, but stylish walking shoes, like these Puma State X Vashties (available from Stadium Goods). A good walking shoe says “casual,” but it also says you’re also a little more sophisticated.

Image courtesy of Stadium Goods.

Another big mistake in going for the casual look is not taking proper care of your sneakers – dirty shoes will quickly degrade your intentional look. Can sneakers be cleaned? Absolutely. Nike recommends using a soft-bristled brush to clean the outsole, and then mixing warm water and a little laundry detergent, and then applying it with a soft brush to the affected area. Follow up with warm water to remove the detergent, and then air dry.

Everyday blazer

The intentional casual look doesn’t call for neckties, but a less formal blazer or sport coat, worn over a solid colored tee or pullover, will accentuate your looks. You can wear it with a button-down shirt, but you don’t have to. A basic tee or polo shirt by itself is okay, but pair it with a casual blazer, and now you’re the man in charge. Feel free to roll up the sleeves.

Shaven face or no?

The “scruffy” look that is somewhere between a five o’clock shadow and a full beard is in style, but not everyone can pull it off. George Clooney can do it with aplomb. Steve Bannon, on the other hand, looks like a hobo. It can be a great casual look if you have the face for it.

Always add a little contrast

Want to really make a big statement? Combine your smart casual outfit with a higher-end piece of jewelry or a perfect contrast. A pair of well-fitting jeans with black walking shoes, a polo shirt and a herringbone blazer with sleeves rolled up just so will be enhanced with the addition of a stylish Swiss watch. The contrast of the casual combination with the more expensive watch makes an important statement. It says, “Yes, I’m comfortable and casual, but I can go full business-formal at a moment’s notice.”

There is no casual “uniform”

Mark Zuckerberg notwithstanding, smart casual means not sticking to a uniform. Jeans-and-tee every day, for most of us, is just lazy. Don’t be afraid to mix it up a little, add some color and even an accoutrement or two.







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