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
Harrison Ford spotted at Barney's New York in Beverly Hills, Calif.
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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.
STEP 3: Get some 'dressy' sneakers
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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
Will Smith sporting an untucked boxy cut shirt.
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
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.