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There’s a difference between looking good and looking like the smartest guy in the room. In competitive industries like finance, politics or real estate, the former just isn’t an option. But how do you pull off the latter? It’s as easy as refining your tie selection to show off your personality and discerning taste at the same time. In order to fly above the sea of navy blazers and tan dress shoes, you have to follow the rules of matching, and yes, there are rules to matching dress shirts and ties.
To take a deeper dive into the world of neckwear, we talked to Greg Shugar, CEO and Creative Director of Beau Ties of Vermont. With nearly two decades in the men’s formalwear industry, and after co-founding The Tie Bar, Shugar now turns his attention to quality, made in the USA craftsmanship. Shugar designs hundreds of neckties and bow ties every year, so who better to help us master the art of matching ties and shirts.
“Wearing a tie used to just mean blending in. It was the male uniform. Now, it’s what sets you apart. It says you care about looking professional, that you take your job seriously (that’s good for your job AND your clients) and it says that personal appearance matters,” Shugar said.
Good neckwear won’t just last, it also won’t go out of style. That’s why allowing yourself to own quality accessories is a must. But simply having great neckwear is only part of the equation — the true test is choosing exactly the right statement piece when getting dressed.
“Start with whatever it is you’re most excited to wear. So if you just got a new suit that you’ve been wanting to show off, then yes, go ahead and start with it. But sometimes it’s a fun patterned shirt or even a unique-colored tie. You should start with the piece that excites you most, and build your outfit around that,” Shugar said.
Most guys have a few outfits they wear that have worked well for them in the past. But there’s a rhyme and reason to creating a dynamic formal outfit, and many times it boils down to learning how to match ties and shirts. To make things easier, we’ve partnered up with Shugar to develop a visual guide to matching shirts and ties.
Use these 10 tips to determine if you should always, sometimes or never wear something together. Some tips are obvious, like avoiding prints on prints. However, keep this guide handy to make sure you don’t turn heads for the wrong reasons by matching your favorite houndstooth tie with your go-to checkered dress shirt.
1. Never: Plaid Tie with Gingham Shirt
“I loathe anything too matchy-matchy. Never wear a tie and matching pocket square or a plaid tie with a plaid/grid shirt. I’ve even seen some menswear shops merchandising their products like this and it’s one of my biggest fashion pet peeves,” Shugar said.
Visually, there’s just way, way too many lines. The eye tries to make sense of each line’s direction, color, size and spacing. Instead of the brain forming a beautiful, cohesive print, the end result is an ocular shit show stuck in a special purgatory in between 2-D and 3-D. A better choice for this tie is a crisp, white dress shirt.
However, this doesn’t mean you should never match patterns with other patterns. In general, you want your patterns to contrast rather than clash. For instance, a gingham shirt can and should be paired with a striped necktie. While the check-on-check pattern will clash horribly, oversized stripes provide a clean visual contrast with the gingham check pattern. This can be a tricky rule to get right, so if you’re new to matching ties and shirts, stick with a solid or herringbone dress shirt when wearing a patterned tie.
2. Never: Floral Tie with Floral Shirt
Attention: SPY Readers. Don’t ever do this when matching ties and shirts.
Following the same rule as plaid with gingham or plaid with plaid (at that point, there’s no hope), wearing floral with floral will only increase your chances of embarrassing yourself. Visually, it’s possibly even more of an eye-strain than our last example because of how much surface area the print physically takes up. It’s hard to mentally decipher unless, of course, you’re a hummingbird.
For instance, we love this floral Worley necktie from Beau Ties, but it looks much better on a solid dress shirt than with another floral print. This is an elementary fashion rule, which makes it all the more distressing to see floral on floral out in the wild. Better choices for this floral tie would be solid shirts in light blue, white or light yellow.
3. Never: Similar Sized Prints and Patterns
This rule may be a bit less obvious than the previous two. You can infer not to pair polka dots with more polka dots. But what about a small paisley print? When it comes to pattern management, it’s best to avoid prints of similar sizes. As we said earlier, contrast is important when matching two different patterns. This is true across the board, for small, medium, and large prints. Pay attention to the amount of surface area occupied and remember that contrast always wins.
From far away, this small paisley print just looks like more polka dots, turning you into walking dotted graphing paper when you don a polka dot tie. A better, and much easier choice would have been this same blue tie, just without the print on it, or a shirt with a large (but understated) grid print.
4. Never: Tie with Pocket Square and Lapel Pin
“I see this all the time. Here’s the Greg Shugar rule. You get a tie or bow tie. And it’s ok if that tie has a tie bar, but you either get a pocket square OR a lapel pin/flower. That’s it. You don’t get both.”
That’s how Shugar got so fly — because he knows when to STOP. Not to bring up overloading visual touchpoints again, but adding too much stuff detracts from the overall look and makes it hard to figure out which accessory is your statement piece. Unless you’re Jennifer Aniston in Office Space, you do not need to wear more than two pieces of flair. That’s true with many types of fashion, but it’s especially important with your formalwear and when matching ties and shirts.
5. Sometimes: The Solid Black Bow Tie
I, the writer, dare you to find neckwear classier than a solid black bow tie. This is a piece everybody needs to own, albeit, with the understanding that it’s not every day, nor every year, that you’ll need to wear it. This kind of bow tie is both understated and also the most bold statement you could make when dressed appropriately. We typically see the solid black bow tie accompanying a tuxedo, of any color, on formal occasions.
Can you wear a solid black bow tie with a regular suit? The answer is maybe, and it depends on where you’re going. If you don’t own a tux, the black bow tie works with the right suit, but you need to pay attention to every detail. All leathers and buttons should be black or very close to it. The bottom line — there’s no need to wear this bow tie to the office.
6. Sometimes: Green Tie with Red Shirt
Certain color combinations have been “claimed” already. For example, we know red, white and blue to represent the United States (sorry, France). We know purple and gold to represent the Los Angeles Lakers. While a green paisley tie and red gingham shirt are perfectly fine individually, together they look like a Christmas card.
Sometimes, this is good. On holidays, at sporting events, in politics, color association may be the key factor to winning over a crowd. There’s a time and a place for everything. For this particular combination, you get a 25-day window during which looking like Santa’s little CPA garners compliments from coworkers. After that, it’s just annoying.
7. Always: Solid Tie with Gingham Shirt
“Safe. Stylish. Versatile,” Shugar notes. We know that successful shirt and tie combinations have contrast. The busyness of the gingham print is balanced out by the lack-thereof of a solid tie. Following this rule, options start to present themselves.
These two ties both work well for this blue gingham shirt. The solid orange tie, drawing inspiration from fictitious style icon, Fred Jones (Scooby Doo, Where Are You?), works well with medium blue, grey or tan suits. Wear the dark purple tie with darker suits, like charcoal or navy blue.
8. Always: White Shirt & Any Pattern
Here’s a stylish formal outfit that works for almost any occasion: “Blue (not navy) suit paired with a white shirt. Patterned tie — can be as crazy as you want.” And how often do you hear, “as crazy as you want,” in fashion advice?
Think of a white shirt as a metaphorical blank canvas. The “blue (not navy)” suit that Shugar describes is essentially the frame. The tie you chose becomes the subject, the star, the focal point of your outfit.
The retro Scarpia bow tie, with a bold mod-style pattern, incorporates browns, golds, and blues. Match this tie to your white and blue base with a pair of tan double monk strap shoes to complete the look. Or swap the colorful bow tie for this grey chevron necktie and add a black leather cap toe shoe or even a clean black suede dress boot to create a compliment-worthy outfit.
9. Always: Light Blue & Brown
When learning how to match ties with dress shirts, it’s okay to stick to the classics. Consider a “light blue shirt and brown/light blue tie,” says Shugar. “A Fashion Editor told me this 10 years ago — light blue/brown is the most underrated color combination in menswear, and she was 10,000 percent right.”
Many guys stick to safe colors: blue, grey and maybe red when they’re feeling a bit frisky. There’s nothing wrong with these colors, they’ll work just fine. Style guys (and gals) with advanced degrees in matching know how to also use the brown family to their advantage. The brown family may consist of chocolate, tan, gold and sometimes certain shades of orange. Both the Doyle bow tie and the Angelotti paisley necktie provide a subtle, sophisticated pop to the shirt. Wear these with a steel blue or tan suit and a pair of chocolate oxford shoes.
10. Always: Textured Ties
“I think a solid textured blue tie is a definite staple, although the least exciting tie. But the truth is, it goes with everything and lets you have a little more fun with your shirt or even your suit. Just make sure it’s not a shiny satin tie — it should have some texture like a knit, wool or spun silk tie.”
It really does go with everything. However, if you want to make this style staple a little more fashion-forward, you can go with a knit tie over a woven fabric. To show you what kind of color combinations work best, we chose two different kinds of shirts to pair with this blue knit tie. One shirt is a purple and blue micro paisley print while the other is a pink and blue gingham. Despite the two different color profiles, spacing measurements, and print styles, this one single tie works perfectly for both.
Some of the quotes in this article have been lightly edited for clarity.