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Ask Mrs Tailor: Valentine's Day Advice

Ask Mrs TailorBefore I begin, I want to introduce myself: I am Mrs. Tailor, the better half of Mr. Tailor. Many of you have been asking him fashion-related questions, so I felt it was time to for a woman’s perspective. After all, when it comes to fashion, women often know what’s best. With Valentine’s Day just around the corner, it’s time to start thinking about what you are going to do, and most importantly, what you are going to wear. Personally, I believe that every holiday is a great chance to show off your charm, especially when it comes to impressing a lady. Valentine’s Day is the one day a year that expectations are high, so let’s talk about how you’re going to woo your dream woman.


I'm going on a first date for Valentine’s Day. I think I’m going to stick to the traditional “dinner and a movie”. What should I wear?
--James in Vienna, VA

I think the dinner and a movie idea is great for a first date. It isn’t too intimidating, and also gives you a chance to get to know each other at the dinner table. Your dinner location will determine the outfit you should choose. For a first date, I would stick to a classic suit and tie—no tux or bowtie needed here. Even if you decide to go on a more casual date, I would encourage you to still wear a button-down long-sleeved shirt, chinos or corduroy pants, and nice shoes. The woman is definitely going to wear a dress no matter where you go, because women always love the opportunity to wear one! You don’t want her to feel overdressed, as that will make an uncomfortable first date even more awkward. Good Luck!

I hang on every word The Tailor says about men’s fashion and being a man. When he suggested a sincere blue suit, I got one. When he taught me about tie clips, I sat up and noticed. He even taught me how to choose the perfect thank you gift. What’s the best advice The Tailor has ever given you?
-- Bart in Baltimore, MD

Mac (that’s my pet name for The Tailor) and I have a wonderful relationship. Since our wedding on the beach at Lake Tahoe and our honeymoon in Anchorage it’ been one wild ride. The best part of being Mrs. Tailor? There’s a never-ending stream of advice dripping from the corner of his hairy upper lip. Much of the time I smile and nod a lot. Which seems to please The Tailor, who assumes I’m agreeing with him. The best advice he ever gave me was to brace myself for one of his kisses because my knees might buckle. He was right.

I’m taking my lady dancing on Valentine’s Day. How should I dress for that?
-- Eric in Washington D.C.

Your top priority is shoes. The shoes you wear should not only be comfortable, but also slip-proof. Most dancing venues have wooden floors, so make sure the soles of your shoes are able to get a grip. Otherwise, you and your lady may end up falling head over heels…right on to the floor! Secondly, you should wear slacks that have a little bit of wiggle room. If you can’t move and shake without busting a seam, you need to reconsider your pant options. Last but not least, wear a shirt color that is sweat-friendly. There is nothing more embarrassing than looking like you spilled a drink down your back. Consider lighter fabrics like linen or cotton, or try a sweat-wicking shirt.

Is it exhausting to be married to the man with all the answers?
-- Dee from Lynchburg, VA

Not really exhausting, it’s actually quite handy. It’s like being married to a Swiss Army Knife with legs. You never know when you may need a corkscrew or a magnifying glass and it’s quite impressive to see a man use a toothpick to skin a muskrat. The Tailor and I are a perfect fit.

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