Menswear Cheat Sheet: How to Pair Shirts and Ties

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Men don’t have a ton of ways to get funky with formalwear. Women get to play pretty fast and loose with such dress codes as “smart casual,” “business formal” and “cocktail attire.” We’ve been at black tie weddings, for instance, where some ladies looked like they were off to Malibu High School Homecoming, and others who took black tie to mean Forever 21 clubbing attire and then others who went the quirky route and looked like they where at a knitting circle in 1953. They all looked perfectly appropriate.

The creative spectrum for men’s formal wear is limited: you get your pants, shirt, tie and jacket to work with. It might seem boring, but it’s actually very challenging and interesting—like going to the opera, or a knife skills class.

Can shirt and tie pairings ever look terrible? Yes, absolutely. Start throwing together your dad’s ‘80s ties with your dress shirts willy nilly, and all hell breaks loose. But put some thought into it, and be the best-dressed guy at the office/your friend’s wedding. Here’s how it’s done:

Solid Shirt

There is no shame in the white shirt game. You won’t get a ton of points for creativity, but do it up right and you’ll out-class the masses. You can get away with any color or pattern tie, but keep it slim to evoke an elegant, classic look. Think more Cary Grant, less Dilbert. If you’re wearing a plain jacket, you can go a little crazy with the pattern or texture of the tie—try a knit or small plaid.

If you’re going the light color shirt route—either a pink, chambray, or sky blue—you have a few options:

•The analogous tie color: Pair a light shirt with a darker tie in the same color family. With a light blue shirt, choose a solid dark blue tie. With pink, go with deep burgundy, mauve or purple. This is a sophisticated, professional style.

•The complementary tie color: For a more creative spin on tie/shirt pairings, consult the color wheel to see which hues complement your shirt. For light blue shirts, this means burnt orange. For light pink, go with green or tan. These pairings are more whimsical than your average white shirt/navy tie combo.

•The contrasting tie color: Contrasting shirt and tie pairings mean business. This is a solid look for your job interview, best man debut, or, you know, State of the Union address. For blue shirts, choose red or burgundy. For pale pink, you can’t go wrong with navy.

Checked Shirt

Gingham and plaid shirts are a safe way to bring some personal style to your office uniform, and this is where tie pairing gets more fun. When you’re shaking up patterns, keep in mind the following:

•Keep the tie pattern bigger than the shirt pattern. Whether you’re wearing plaid with polka dots or checks with stripes, make sure the pattern on the tie is larger so it stands out, rather than getting lost against the shirt.

•Textured ties look much better with checked shirts than plain silk ones. Tweed, wool flannel, seersucker, or knitted ties add visual depth to your outfit. Visual depth is what we’re going for. With a patterned shirt, your tie needs to hold its own in the outfit, and adding texture is an easy and attractive way to do that. Heftier fabrics like wool look especially elegant with plaid in the colder months for a fancy lumberjack vibe, and lighter fabrics like seersucker look light and fresh with gingham in the summer.

•When pairing a solid tie with a patterned shirt, keep the tie darker than the shirt. An easy way to choose a tie color is to look for a base tone in the shirt and match it with that. So if your shirt is red and blue plaid with some cream and brown base lines, go with a solid brown tie.

Striped Shirt

The no.1 rule of tie/shirt pattern pairing: vary the size and scale of your patterns. If you’re combining stripes with stripes (you rebel), contrast them as much as possible. So if your shirt has thin vertical pin stripes, find a tie with bulky diagonal stripes. Get it? Clear contrasts are pleasing to the eye and show intentionality.

When it comes to pattern combinations, you can get more wild with striped shirts than you can with checks. Checks are already very visually stimulating, but stripes are more neutral. While it’s too much to pair a paisley tie with plaid, for example, paisley is fair game with a striped shirt.