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Ask The Tailor: Wool Suits and Shoe Trees

The Tailored ManIt’s time again for Ask The Tailor, and this month he’s working overtime, answering 20% more questions at no extra charge. You’re welcome.

When is it too early to wear a wool suit?

Wooly Willie in Dale City, VA

You got it backwards, Willie. Cotton suits have a season, but you can and should wear your wool suits at any time of year. A wool suit is the staple of a man’s wardrobe, along with brown loafers, a denim shirt, a corduroy jacket, and a derby hat. At least that’s what The Tailor reaches for in his closet. Get a cotton suit for more casual events in the warm months, but wear your trusty wool suit for everything else in any month.


I was taught that a man always pays for dinner on a date, but increasingly women are offering to foot the bill. What’s the right thing to do when she reaches for the check?

Benjamin Banks in Toronto, ON

Don’t have alligator arms, but also don’t fight her over it. Many things have changed since The Tailor’s dating days, but as Sam Cooke sang “Change Gonna Come,” and there’s nothing wrong with that. Many ladies want to pay their own way and there’s a simple rule for this: if you ask her out, you pay; if she asks you, let her pay. If you’re her guest, still make an offer, but if she insists on paying the bill, let her do so, don’t give her a case of “cold coffee” as we said back in my day. If it’s an expensive dinner date and you mutually agree, split the bill, but always make an offer to pay. Don’t be cheap, but also don’t be that fella who is wrestling his date for the check just to seem like a man. Another nice gesture is to take care of the gratuity when she pays the bill or let her do the same when you pay.

How do I select a pocket square and when do I know if a pocket square is appropriate?

Square Deal Sam in Portsmouth, VA

Have you been stalking The Tailored Man? This month over on their website they have a guide to pocket squares (imagine that). Head over there for a fizzing explanation on everything square, but here are some things to help you get started. A pocket square is never inappropriate but the occasion dictates the style you go with. Choose the square-fold or the puff depending on your situation. More formal, go square-fold, more casual choose puff for a flash of color and style. And do not under any circumstance ever match your pocket square precisely to your tie. That’s silly and you deserve to be ridiculed if you do it.

I have a friend who uses a shoe tree for all his shoes. Should I be using a shoe tree or is this guy just a show off?

Carlos in Washington D.C.

It sounds like you might be trying to keep up with this pal of yours, is that so Carlos? If he has style and he takes care of his clothes then he’s a good man to emulate. Why do we use a shoe tree? They prevent moisture buildup for one, but the most important reason is to maintain the shape and size of your shoes. The tree prevents or lessens the likelihood of creases in your leather shoes.

Todd Graf, Manager of Cedar Products Division for Allen Edmonds in Washington D.C. explains that it also keeps the shape looking new and it extends the life of your shoe. Because of that last reason, investing in a shoe tree (usually about $20 for a cedar shoe tree) is a wise decision because you’ll have to replace your shoes less often. I don’t necessarily think you need a shoe tree for each pair of your shoes, but a few for your best shoes and to rotate for the shoes you’re wearing the most is a good strategy. Get cedar shoe trees because they also help add a rich cedar smell to your shoes.

“Shoe trees are commonly thought of as a good thing to use on your ‘nice’ shoes.  This is true, but in reality they offer a value added benefit for all your shoes,” Graf says. “Eastern Red Cedar ferociously absorbs the sweat out of your shoes, and the heart wood is where the natural deodorizing oils are held that keep your shoes smelling good.”

Another thing you may not know: if shoes go unworn for a long period of time they shrink. A shoe tree prevents that shrinkage and protects your little piggies from being squished.

I’m heading out on a one-week trip to Asia and I can’t pack much more than one medium-sized suitcase. I’ll have a mix of leisure time and social engagements. I want to look good, what clothes should I pack? Also, where does The Tailor like to go on vacation?

Bags Packed in La Plata, MD

I’ve bounced around the globe a few times and usually I travel light. One can do that and still dress like a gentleman with style if you follow these tips:

  • First thing you do: pick a color to base your travel wardrobe around. It can be anything: brown, gray, navy, black, white or cream, etc. Make your slacks, jackets, and shoes this color and then build out from there. You only need 2-3 pairs of pants for a short visit like a week.
  • Your shirts, hats and scarves should be complimentary to your chosen base color. This is a chance to add color, so brighten it up.
  • Higher quality clothing handles the wear-and-tear of travel better than cheap clothing, so buy the best you can afford. Especially when it comes to shoes and pants.
  • Take light clothing items and make sure they are easily cared for, you want to be comfortable and free from having to press or iron or wash (you may not have time).
  • When you’re on the plane wear your heavier items, like your coat, so you don’t have to shove it in your luggage and risk wrinkles.
  • Ensure that each item of clothing you pack can be worn with every other item so you’re versatile on the road. When stuck on whether to bring something, ask yourself if you really want to haul it across the world, if you can’t answer immediately “Yes.” Then leave it at home.
  • Take a blazer, one nice shirt, and a tie: it can dress up anything and serve in most social situations.
  • Bring walking shoes that are comfortable for exploring your area. Otherwise, maybe one other pair of comfortable shoes in your primary color, but no more. Shoes take up too much space.

You asked about my chosen travel spots. The South Pacific will always be one of my favorite locales because it was the first place The Tailor sailed when I was a young man working on a tall ship. The islands of Oceania are beautiful and still have a hint of exotic remoteness. I’ve also enjoyed trudging across Europe on foot and by train. I spend a lot of time with my often-broken nose in books at shops in Spain, Germany, and Greece. Years ago I spent a month in Asia’s mainland enjoying the food and the spices. Bon Voyage, my friend, and say hello to the Dalai Lama!

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