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Ask The Tailor: The One-Suit Man, Growing a Beard, and Watches

Ask The Tailor at The Tailored ManAfter laying the foundation last month with his first batch of advice, The Tailor is back and ready to be challenged with your questions. Come forth, ye needing wisdom, and huddle at the finely-shined shoes of The Tailor.

I have the resources for one suit and I want to be able to wear it year round for all occasions. What should I be looking for?
— One-Suit Charley in Culpeper, VA

Dear Charley,

You can’t go wrong with a blue suit – it’s appropriate for all seasons and versatile enough to wear for any occasion. Whether it’s a wedding, special occasion, funeral, or a night out, a well-tailored blue suit is a must in any gentleman’s collection. Start with the blue suit and grow your wardrobe from there.

The Tailor has a few secrets he can share --- purchase a colored shirt or a pinstriped shirt to spice up the solid suit when needed. Also, don’t buy a pinstripe blue suit if that’s all you’ll have. It stands out more and people will easily notice that you’re a one-suit man.


Winter is around the corner and I want to grow a beard. I really love your sideburns and bushy mustache – you’re a man who knows how to do facial hair without looking sloppy. What’s your advice for growing a full, impressive beard that will get me noticed?
— Wanting Whiskers in Annapolis, MD

Dear Whiskers,

So you want facial hair like The Tailor, do you? It’s not likely that you can pull off the sideburns and healthy mustache that adorns my face (my mustache can beat up your beard), but by paying special attention to some simple rules you can have manly facial hair that others will envy. Lucky for you, The Tailor has had a beard at several stages of his life (he even wore mutton chops for a spell).

First, consult with your favorite barber before you grow the beard. Tell him what you plan to do and have him manicure the beard in its early stages.

Second, trim the beard neatly as it starts to grow out, but don’t inhibit the natural growth of your facial hair. Let your chin express itself.

Once you have a lengthy beard, see that barber again and have him trim it to style. Pay close attention to what he’s doing and ask him how to maintain it.

Don’t ignore your new furry friend. Remember what author Kurt Vonnegut Jr. said: “Everyone wants to build, but no one wants to do maintenance.” A well-maintained beard will make your handsome face even more attractive, and it’ll keep your cheeks warm too.

The cool weather is coming and soon I’ll have to break out my suit jackets. What jacket do you recommend?
— Johnny Jacket in Baltimore, MD

Dear Johnny,

Have you been hanging out with Whiskers from Annapolis? You’re both concerned about the cooler weather, and you’re right to be --- it’ll be here before you know it. Want to stand out? Do what The Tailor does, wear a custom tweed jacket. Many a time The Tailor has drawn attention for his well-crafted tweed jackets.

As the Gentleman’s Gazette recently pointed out: “Some view tweed as an itchy, stuffy, stodgy fabric only worn by aging northeastern college professors or by English gentry in the Scottish dells,” but many stylish men have rocked the tweed.

First made fashionable in the 19th century, tweed is not only trendy, it’s practical because it keeps you warmer and it holds up over time and wear. See your tailor to have a Tweed jacket made to your specifications. The Tailored Man has several styles that will help you capture the classic look that only tweed can supply.

My husband’s birthday is in two weeks and he keeps dropping hints that he wants a briefcase. I want to get him something very nice that will last a long time. He’s a marketer and he dresses nicely for work.
— Generous Wife in Montreal, Quebec

Dear Generous,

A marketer, is he? Ask him why it is that every time The Tailor goes to the grocery store the cart always has one wheel that’s rolling in the wrong direction. What - not that sort of market? Ah well.

There are three ways to go: the standard folio briefcase, the portfolio, and the attaché.

The folio case is a briefcase with a handle and soft sides, which make it easier and more comfortable to transport. The Tailor doesn’t like the folio case because his large hands fumble with the snapping and lacing fasteners.

The portfolio does not have a handle and is also soft-sided. It’s extremely portable but informal.

Finally there’s the attaché, the choice of businessmen for decades. The attaché is sturdy and secure --- it often comes with a lock. It’s hard-sided and rugged, however it’s less comfortable to lug around. An attaché can have one or more compartments and it’s great for toting papers, briefs, books, your corned beef sandwich, just about anything.

Either brown or black leather will go well with anything. For a nice touch have your husband’s initials engraved on the briefcase.( The Tailor’s are WSB, hint hint).

I just purchased a Diesel watch and I frequently wear it with my suits. Where should the cuff of my shirt be? Should it cover the watch or no?
— Big Hand in Toronto, Ontario

Dear Big Hand,

Here’s the rule: the cuff of your shirt should cover no more than half of the watch. You can have your cuffs tailored this way (based on the size of your typical watch) and adjust the placement of the watch on your wrist according to the size of the band or watch face. Two more tips from The Tailor: always be prompt, and never look at your watch while engaged in a conversation.

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Send your questions to The Tailor via posts on Facebook at If your question is selected you will receive nothing, but you will be able to tell your friends that for a brief moment The Tailor was thinking about you.

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