1. Honor thy tailor
Even the best suits need altering. Pants need to be shortened, jackets need to be brought in, sleeves need to be narrowed (yes, you can ask your tailor to slim down your sleeves), and buttons need to be realigned with buttonholes (most guys’ shoulders aren’t entirely even, meaning your jacket often sits a bit askew). You should always buy your correct size, but you then need to have a tailor customize it to your body. It’s the difference between being appropriately dressed and being stylishly dressed.
Suit, $1,295, by Valentino. Shirt, $400, and shoes, $500, by Prada. Tie by J.Lindeberg.
2. Thou shalt wear sneakers made for a man
It’s fine to own crosstrainers and running shoes and hightops. But save them for the gym. When you’re on the street, keep your sneakers simple and classic. Go for ones like Stan Smiths, Jack Purcells, and Sambas. They work with everything, including suits.
Sneakers, from top: Samba by Adidas, $75. Carnaby Retro by Lacoste, $85. Jack Purcell by Converse, $70.
3. Thou shalt invest in the right timepiece
Buy a high-quality stainless-steel watch. It looks as right with jeans as it does with your best blazer.
Rolex, $3,250. Shirt, Polo by Ralph Lauren. Pants by Ralph Lauren Purple Label.
4. Thou shalt match your socks with your suit
When choosing socks, the basic rule is to consider the suit instead of the shoe—in other words, if you’re wearing a navy suit with black shoes, reach for navy socks. And when wearing a light suit, make sure the socks are darker than the suit but a shade or so lighter than the shoes.
Suit, $1,850, shirt, $545, and shoes, $520, all by Prada. Vintage tie by Helmut Lang. Socks by Pantherella. Watch by Breitling.
5. Thou shalt not wear a tie that is too slim
Unless you’re a hard-core fashion guy who favors a superskinny tie, stick with one that measures about three inches at its widest point. It will be narrower than traditional ties, but not by too much. Tie one on and you’ll look modern and sophisticated.
Ties, from left: Gant, $85; Ted Baker, $75; Tino Cosma, $95; Vintage by the Aron Group, $39.
6. Thou shalt put your wallet on a diet
Your wallet should not be as fat as a burrito. In fact, you should get rid of your wallet and, while you’re at it, trash all the receipts, video cards, and other unnecessary crap that’s stuffed in it. Buy an elegant, slim leather credit card holder and stock it with your essential cards. Then, fold your cash in a money clip. All that other nonsense can go in your desk drawer. You don’t need it.
Credit card holder, $35, by J. Fold.
7. Thou shalt wear the right tie with the right tux
Two points to remember: (1) A bow tie goes best with a peak-lapel tuxedo, while a straight tie works better with a notch lapel. (2) Regardless of what kind of tie you’re wearing, make sure the fabric matches the lapel. If your lapel is grosgrain, your tie should be grosgrain. If your lapel is satin, your tie should be satin. And one more thing: Your tie (no matter its shape) should be black. Colored ties are for the prom.
Tuxedo, $1,895, by Calvin Klein Collection. Shirt, $165, by Thomas Pink. Bow tie, $40, cuff links, and studs by Paul Stuart.
8. Thou shalt wear brown shoes—with nearly everything
Black dress shoes are easy—they’re understated and tasteful. Brown dress shoes up the style factor. People notice them. They go best with gray, khaki, or navy. Dark brown shoes are easier to pull off than light brown ones.
Shoes, $790, by J.M. Weston. Suit pants by Tommy Hilfiger.
9. Thou shalt learn when to cuff ‘em
If you’re wearing a trim, modern suit with flat-front pants—the kind often shown in this magazine—you should not cuff your pants. However, if you’re a guy who likes a classic suit with a single pleat, go for a cuff—but not more than one and a half inches deep.
Suit, $3,295, shirt, $325, and tie, $135, by Ralph Lauren Purple Label. Shoes, $575, by Ermenegildo Zegna Couture.
10. Remember thy undershirt
This one’s tricky. If you’re wearing a conventional white broadcloth dress shirt (which means it’s fairly see-through), you have two options: Skip the undershirt and you’ll look clean and stylish. Or, if you’re a hairy guy who perspires a lot and you feel safer in an undershirt, wear a crewneck. The lines of a V-neck or tank top will be visible beneath your shirt and tie and you’ll look cheesy. If you prefer a V-neck or tank top, you might consider other dress shirts. Go for ones with checks or stripes, which make an undershirt less visible. Or opt for hardier fabrics, like an oxford cloth, which make undershirts all but invisible.
Shirt, $325, by Lorenzini. T-shirt, $17, by Calvin Klein Underwear. Tie, $39, Vintage by the Aron Group.