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Ask The Tailor: Mixing Patterns and the Best-Dressed Man in U.S. History

Here we are with another round of Ask The Tailor, the man who seems to know it all without being a know-it-all.

What are the things to consider when mixing patterns in my wardrobe?
— Steve B. in Grantsville, WV

Bravo to you for taking on the challenge of mixing patterns. Any man can wear solids that match. Any man can toss a bold-patterned tie around his neck to seem a little daring. But not all men have the chops to mix patterns. Once you pull this off (with my help), dors are going to open for you, my friend. The world will seem like a happier place and women will turn their heads. Prepare to be coveted.


First, make sure the patterns are different sizes. If you have pinstripes on your jacket, make sure the shirt or tie has stripes of a different size. Use the same strategy with prints: take a keen look at the size of the primary item in the print (a sailboat or a flower etc.) and make sure it’s smaller or larger than the other prints you’re wearing.

When in doubt, consult this handy online guide from Attire Club

Will I regret getting a tattoo?
— Bobby in Stafford, VA

I can’t be sure. Does it say “Debbie, My One and Only Love” and did you just meet Debbie four days ago? Or does it say “MOOM” instead of “MOM”? The thing about decisions we make when we’re young men: often we don’t know how critical they are until we’re staring at a policeman’s baton or sitting on a park bench shaking our fist at the sky. “Damn you, Ryan Seacrest!”

The Tailor can assure this: if the tattoo is trendy or steeped in pop culture, you may want to hold off. How ridiculous would you look now with the Mork & Mindy tattoo you got on your chest in 1979? Stick with something time-tested like an eight ball or a cougar. People think cougars are cool. Also, never get a tattoo from a man who’s not wearing a shirt or after 2 AM. Lastly, no neck tattoos, okay Iron Mike?

I have a lot of bright colors in my wardrobe and I can do black and brown really well. Am I overlooking anything?
— Andre in Bethesda, MD

Andre sent me a few photos and he’s a dashing lad with impossibly broad shoulders that make me hate him. He has a face that makes women forget guys like me exist. Andre my boy, you may have forgotten a little friend of mine I like to call “navy.” Every man needs navy in his wardrobe (it’s “the other black”). Pick up a sharp navy belt and make sure you have a few pairs of navy trousers and socks. The tailor likes to have navy loafers on hand as well. Over at Dappered they have you covered on navy and of course the fine folks at The Tailored Man can drape you in navy if that’s your dream.

My neighbor thinks he’s the best at everything. I want to host a barbecue/swim party that will put him in his place and amaze my guests. How do I do that?
— Ellis V. in Tysons, VA

Revenge is a dish best served cold, but the best barbecue features a grill heated between 450-600 degrees. In order to humiliate Mr. Neighbor, you’ll need to bring the heat. Here are grilling tips for your backyard bash:

1. Grill steak, it’s the best option for open flame cooking. If you insist on something else, choose pork, it’s juicier than chicken and easier to grill.

2. Hover your hand low over the grill and if you can keep it there for 3-4 seconds it’s not warm enough. You should only be able to keep your hand there for 1-2 seconds. Buy as much grill as you can afford, the more evenly distributed heat the better, it doesn’t need to be gas or propane, but that helps quite a bit. Why fuss over wood or charcoal?

3. After you remove the meat from the grill cover it and let it sit for 15 minutes. This allows the natural juices to seep back in, adding flavor.

I suppose you also want to dazzle your guests with refreshments. Make sure to have plenty of COLD drinks on hand for guests of all ages. Stock a cooler with water, soft drinks, and juice boxes, and another with beer. To really make an impression, employ a bartender so you can offer a selection of drinks. Here’s a list of tasty drinks appropriate for the poolside, including one with the tongue-tying name “Boozy Strawberry Lemonade Vodka Slushy.”

Decorate the backyard and have plenty of lighting in case the festivities roll into the evening (making the neighbor even more envious). And remember to rock that bathing suit.

If you were stranded on an island and could only have one pair of sunglasses what would they be?
— Morgan in Pleasant Valley, WV

Have you been reading the first draft of my memoirs? The Tailor was once stranded on an island, and though it seemed perilous, I enjoyed my few hours as a real-life “Robinson Crusoe.” I only wear the Randolph Aviator II. If it's good enough for the U.S. military, it's good enough for me.

I’m an American History major at Georgetown, who would you say was the most stylish man in the history of the United States?
— Amanda in Washington D.C.

Many people will choose JFK (a favorite of Mrs. Tailor), but I always admired the sartorial perfection of Fred Astaire, a man who could sleep in a suit for a long weekend and still look brilliant. Mr. Astaire always looked fresh and dapper. Maybe it was his lithe, long-limbed, graceful frame that I admired so much. Find a photo of him not looking dashing. I dare you.

Also, don’t overlook our best-dressed American actor (Paul Newman), best-dressed American-born author (Bonfire of the Vanities mastermind Tom Wolfe), and best-dressed revolutionary (Gilbert du Mostier, also known as Marquis de Lafayette). Lafayette, we are here, and we salute your style.

Below L to R: John F. Kennedy, Fred Astaire, Paul Newman

best dressed men in history

Join the discussion on our Facebook page and tell us your choice for most stylish man in U.S. history.

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