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Guys: 5 Ways to Update Your Weekend Look

Two words: sneaker wardrobe. Tips for looking casually cool, at any age

spinner image Dennis Quaid, Hugh Grant, and Ted Danson casually dressed in sportcoats and slim fitting jeans
From left: Dennis Quaid, Hugh Grant and Ted Danson unglue their suits and turn their jackets into stylish blazers.
Ray Tamarra/GC Images; Stuart C. Wilson/Getty Images; Jason LaVeris/FilmMagic

For as much as some of us may have complained when we wore suits every day, they made our life easy. When it was time to dress, you simply put on two nicely tailored garments that were guaranteed to match. You really had to work hard to screw up the rest.  

Now, a new air of casual has become pervasive, whether you're dining out, going to the theater or to work, or even, sometimes, attending a special occasion. You have the freedom to wear what you please. Young guys love it, but for the generations more accustomed to  dress  codes, the response is often more like, “Yikes!  Now  what do I do?”

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First, take a breath and remember: They’re just clothes. Now, take a realistic assessment of your current wardrobe in terms of how it fits your daily life, and whether it makes you feel comfortable and confident. More than likely, you’ll discover that you need only make strategic adjustments, not undergo a major overhaul, to go casual with cool confidence. So, working both with what you have and a few things you need to get, let’s spiff you up.

You'll want to pair this jacket with relatively slim-fitting, flat-front pants. (Pass on the pleated kind, please, as well as all those pants in your closet that I'm betting a pair of Super Bowl tickets are probably one or two sizes too big, especially when it comes to the rear view. Want proof? Look in a three-way mirror.) Jeans are a no-brainer with something like a navy jacket, but you'll want a pair in a darker wash, for that slightly dressier look. You can alternately look for casual pants that offer a little stretch so they hold their shape and look a little sharper than, say, basic cotton chinos.

STEP 2: Step inside a store 

spinner image  Harrison Ford sighting at Barney's New York
Harrison Ford spotted at Barney's New York in Beverly Hills, Calif.
Nick Smith/Getty Images

To make changes such as finding a great pair of casual pants or jeans, you really need to shop in a brick-and-mortar store, and one known for competent service, such as Nordstrom, J. Crew or even Uniqlo (it's not just for kids). Don't be afraid to ask for, or accept, a few suggestions about styles or sizes, and don't forget to use those helpful three-sided mirrors. My other shopping advice is this: Don't shop with any woman you’re emotionally connected to. Her view of you is distorted by history and love. To see yourself in a new light, you need a fresh pair of eyes. Finally, you need to take the time to try clothes on. You may hate shopping, but my guess is you hate looking uncool even more.

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STEP 3: Get some 'dressy' sneakers

spinner image A collection of stylish white sneakers for casual male style
Topic Images/Getty Images

Sneakers are now ubiquitous and worn with everything. However, don’t pull out your running shoes or the ones from your gym locker, if only because they are probably either streaked with neon orange or yellow and sweat-stained. What’s required are some sleeker sneakers. I like styles that are black or solid colored on top with a white banding on the bottom (Cole Haan and Vince have great options along these lines), or a classic all-white sneaker, such as Converse Chuck Taylors, or those from brands like Van’s, K-Swiss or Superga. None costs a fortune, so you can buy a few.

STEP 4: Consider the shirt tuck

spinner image Will Smith on the red carpet wearing a colorful untucked polo with jeans and white sneakers
Will Smith sporting an untucked boxy cut shirt.
Thaddaeus McAdams/FilmMagic

I am not a major fan of untucked shirts. I feel that as we age, both men and women look better when we appear more pulled together. (Frankly, not to sound retro, but, when appropriate, a well-cut dark wool suit, crisp white shirt  and  solid tie can still knock 'em dead.) But if you want to go the untucked route, don’t reach for your old dress shirts to go with your slimmer-fitting jeans from Step 2. What you need is a shirt with a boxy cut (but slimmer fit) and a squared hem, possibly with side vents. It should look like it was designed to be worn outside of your pants. If your waist is thinner than your hips, you can get away with a shirt like this. If that’s not the case, for your untucked look, opt instead for a lightweight, knit pullover with an unribbed bottom.

STEP 5: Wear a handsome casual watch

spinner image Shinola casual analog watch with stylish leather band
Courtesy Shinola

Pragmatically, your smartphone has eliminated the necessity of strapping on a timepiece — except the right ones look so handsome. It should be analog, not digital, with a leather band, a clean face and not a lot of hardware. Preferred, reasonably priced brands include Komono, Shinola ( personal  favorite), Skagen and the never-fail Timex Weekender. Find one that speaks to you, then consider it the finishing touch on your new casual look — one I'm hoping helps you walk taller and prouder every time you head out.

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