Mistake 1: The Schlumpy Leather Jacket
Problem: There’s nothing modern—or even retro-cool—about a leather jacket that fits like a rain poncho.
Solution: When trying on a new leather jacket, keep going down a size until you can’t get it on, then buy the next size up. It should feel snug as a wetsuit but will take your body’s shape over time. The coolest style right now? The bomber you see here.
Jacket, $1,695, by Dolce & Gabbana. Shirt, $375, by Balenciaga by Nicolas Ghesquiére. Khakis, $48, by Dockers. Shoes, $488, by Brooks Brothers Peal & Co.
Mistake 2: The Barack Obama Jeans
Problem: Whitewashed high-waisted jeans aren’t just dorky—they also emphasize all the wrong parts of your body.
Solution: Medium-rise raw denim jeans sit at the most flatter place (on your hips), follow your legs (instead of saddlebagging out from your waist), and form-fit to you as you break them in. Oh, and while you’re at it, replace the Seinfeld-esque running shoes with some lace-ups or classic sneaks.
Jeans, $90, by Martin + Osa. Sweater, $100, by Uniqlo. Shirt, $40, by H&M. Shoes, $560, by Alden. Watch by IWC.
Mistake 3: The Cheap Printed Tie
Problem: Let’s pretend this tie isn’t a little ugly. And tied too long. It still isn’t working. Why? A cheap thin silk tie gets you an unacceptably tiny knot.
Solution: Go for a sturdier silk, which’ll make for a solid knot. Plus, keep any patterns understated. Also, a quick note on length: The tip of your tie should not hang below the waistline of your pants.
Tie, $135, by Ralph Lauren Black Label. Shirt, $360, by Etro. Pants, $280, by Acne. Tie bar by Kenneth Cole.
Mistake 4: Sagging Suit Pants
Problem: Just bought a cool skinny suit? It ain’t cool if it stacks up at your ankles like baggy jeans.
Solution: Take your suit to a tailor and tell him you don’t want a break. Those are the words you should use: “I want this suit hemmed with little or no break.” Period.
Remember: Tailors are used to working with guys who don’t know what they want. Be assertive so he understands that you’re after a specific look and don’t just want “the usual.”
Suit, $1,095, by D&G. Shoes, $395, by Calvin Klein Collection.
Mistake 5: The Pancake Collar
Problem: When you’re not wearing a tie, the collar on your dress shirt flattens out and sinks beneath the lapels of your jacket. The look? Sloppy.
Solution: First, look for dress shirts with firm collars that stand up on their own., framing your face. Second, use collar stays. You know, those little plastic things. Every proper dress shirt has slots for them.
Shirt, $150, by Thomas Pink. Suit, $1,195, by Emporio Armani.
Mistake 6: Right Suit, Wrong Belt
Problem: You want Tiger Woods’s swing, not his style, especially when wearing a suit. A silver-tipped faux cowboy belt is not a dress belt. If you’ve got one, retire it.
Solution: Invest in a high-quality leather strap that’s an inch to an inch and a half wide. If it smells and feels buttery, that means it’ll age beautifully. And the buckle should be subtle.
Belt, $69, by Club Monaco. Shirt, $370, by Marc Jacobs. Pants, $195, by Boss Black.
Mistake 7: The Oversize Suit
Problem: You invested in a dark handsome suit, but you look a little…eh in it. Know why? It’s a size too big, and all that extra material is boxing (shoulders), sagging (waist), and flopping (ankles).
Solution: Repeat the leather-jacket method from the opening page. When trying on a suit, keep going down a size in the jacket until it gets uncomfortable. Then go one size up and buy that. And unless you’re over six feet two, buy a regular length, not a long.
Suit, $1,395, and shoes, $395, by Calvin Klein Collection. Shirt, $360, by Etro. Tie, $150, by Black Fleece by Brooks Brothers.