Shopping Tips for the Style-Challenged Man

By Glenn O'Brien | Boston Magazine |

Nine wardrobe guidelines that can take any guy from slapdash to dashing.


1. PANTS, A PARADIGM SHIFT Men’s clothes don’t change much. But once a decade or so there’s a shift. There’s a yin and yang of tailoring, and we are now in a yin moment, as in the ’60s, and pleats (as you should have noticed) are out. Ava Gardner’s scathing comment on Howard Hughes’s style was that he wore “pleats that went out with dueling.” This is a flat-front-pants moment. Get with it. Our pick: Modern Amusement pants, $125, Uniform.

2. FLAIR—GET SOME Want to wear a Red Sox cap? Fine. But it won’t replace a fedora with a polo coat. Don’t be afraid to wear a real hat when you’re in tailored clothing. That breast pocket? How about a pocket square? Good for crying ladies, sudden sneezes, a tourniquet. Socks? Don’t match them to your shoes; they’ll look like booties. Freelance with a little color from your shirt or tie. Our pick: Massimo Bizzocchi silk pocket square, $55–$65, Louis Boston.

3. YOU’VE GOT MUSCLES? Here’s a question: You go to the gym, so why the fake shoulders? Supersizing is out, and the natural look is back, bigtime. Lots of the season’s best sport jackets are as unstructured as a shirt or sweater, and it’s a casual yet hip, sophisticated look that’s in keeping with the very best moments in American and British tai-loring. Our pick: Etro unstructured two-button blazer, $730, Barneys New York.

4. SEMPER UBI SUB UBI That’s Latin for “Always wear underwear.” Underwear, not rags, which may feel comfy but look suspicious. Everything most people won’t see should be as pristine as everything that’s visible; nothing scares off potential intimates more than sloppy underwear. Even if no one will see them, respect yourself. Throw out anything you haven’t worn in a year. Don’t look back. Our pick: Hugo Boss boxer briefs, $20 a pair, Hugo Boss.

5. FORGET THE LOBSTER BIB Ties now are slimmer but still not as slim as they will be. In the big, double-breasted ’50s, men wore big, fat ties, which came back with the football-shouldered power suits of the ’80s and ’90s. These days, the width of your tie should match the width of your lapel. (Want to know a secret? Fashion stylists alter designer ties for photo shoots to make them skinnier.) Our pick: Marc Jacobs 2-inch silk tie, $75, Marc Jacobs.

6. UNBUTTON YOUR MIND Pay no attention to those congressmen on TV. The
button-down collar isn’t a feature of a proper dress shirt. It was originally intended to stop your collar from flapping in the breeze while playing polo. If you’re not playing, if you’re being serious—go with something more sophisticated, like a plain turn-down collar. Never dress like a congressman. It’s the mark of a rube. Our pick: Acne dress shirt, $225, Stel’s.

7. CASUAL, NOT UNCONSCIOUS The casual workplace isn’t meant for shorts, sneakers, T-shirts (especially ones you have to read), or jeans with holes and abrasions (real or manufactured). If you can’t wear it on a private golf course, it doesn’t belong in an office. Bruins or Patriots jerseys are not sweaters. Anyone can dress up, but having style is knowing how to dress down. Our pick: Paul Smith chocolate velvet blazer, $620, Riccardi.

8. SUITABLE SUITS Go for hand-tailoring, not big names. (The price is paying for the ads.) Ask if the jacket is basted (hand-stitched on a canvas shell) or fused (glued together). Both look good walking out the store, but fused suits don’t hold up to dry cleaning. And make sure it fits. Most men’s suits don’t. This problem reaches the highest levels of government. Our pick: Brioni Millenio three-button wool suit, $4,475, Louis Boston.

9. ATHLETIC SHOES ARE FOR ATHLETICS Sneakers don’t go with a suit, unless you suspect you might have to run for your life. Every man needs black and brown leather dress shoes. Loafers are for loafing—not for funerals, court appearances, life-changing experiences. But a man needs a pair of genuine casual shoes, not something meant for a gym or a boat. Our pick: Alexander McQueen for Puma leather shoes, $225, Alan Bilzerian.