We see it all the time, even on the stylish streets of New York: men in oversized khakis, button ups, and even shoes (usually of the clunky square-toed variety). But even worse, these guys are fit, good looking, twenty to thirty-somethings not dressing to their full potential. (For style inspiration from guys who do it right, check out Street Scenes: New York Fashion Week.) See, dressing younger doesn’t mean digging up your old tees from college and wearing a backwards cap. Surprisingly enough, it just means not dressing older. Here are the top fashion fails that age you—and how to fix ‘em for your best look yet.
Bulky sports coats
A boxy, bulky jacket is about as flattering as a Snuggie. Even if you’d like to drop a few pounds, we promise that a fitted one will look better. The shoulders should rest firmly on the edge of your actual shoulders, the sleeves should fall around your wrists and let ¼ inch of shirt cuff show, and you shouldn’t be able to fit a six-pack of beer between your jacket and your torso. Unfortunately.
Look younger: Bookmark this article and walk into your closet right now. Find all of your blazers, put them in a bag, and see your tailor immediately. You may think they fit fine, but good tailoring is the difference between fine and damn fine.
Oversized dress shirts
You probably wear a button front to work, right? And you probably want to be seen as confident and powerful, right? That’s not going to happen in a shirt that says, “I’m hiding in a sea of fabric because I’m not secure enough to wear something slimmer.” It not only ages you, it makes you look unsure of yourself. And if there’s one thing CEOs have in common, it’s looking assured . . . even when they aren’t.
Look younger: Look for shirts labeled “slim fit,” like this one from Banana Republic. You’ll avoid a boxy silhouette, flatter your frame, and not make your 175-pound body look like Philip Seymour Hoffman’s.
Clunky shoes
They might look comfortable, but since your foot isn't square-shaped, they're no better than a classic, rounded toe. In fact, clunky, square-toed shoes are the easiest way to destroy a perfectly good look. Even the most tailored, high-end suit will look cheap if you finish it off with a pair of plodders.
Look younger: Upgrading your below-the-ankle style doesn’t mean dropping serious dollars and developing blisters. You can buy a versatile pair of oxfords for under $200, ones that you can wear anywhere and everywhere. Exhibit A: this pair from Kenneth Cole.
Dad jeans
Despite the name, Dad jeans are worn by well-meaning guys of all ages. How do you know if you’re guilty? Your jeans are high-waisted, baggy, and somewhat stiff. Oh, and a belt worn at your belly button takes it to the next level. (In case you can’t tell: This is not a level you want to be on.)
Look younger: The waist of your jeans should fall right around your hipbone. Any higher could make you look like Mitt Romney, any lower and you’ll be flashing strangers every time you bend to tie your shoe. You can’t go wrong with one of these New Jeans for Fall.
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