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Ask The Tailor: Buying Shoes, Presidential Drinks, and Pork Pie Hats

Ask The Tailor

We’re gearing up for summer and The Tailor’s mail bag is overflowing with questions. This time he tells us why custom made shoes are more comfortable and what type of man looks great in a pork pie hat, and he reveals JFK’s favorite beer.

I‘ve stopped buying “off the rack” and never looked back. I look great in my custom-made suits and I get compliments all the time. Thank you. But I buy my shoes “off the shelf”. Should I have them made especially for me too? – Clyde in Cooperstown, NY

The short answer is “yes.” But there’s also a second answer which is “not always.” Custom shoemaking was the only way to get shoes up until the mid-nineteenth century when mechanized manufacturing processes were developed and perfected. Suddenly almost anyone could get quality shoes easily and much cheaper. But that doesn’t mean their feet were happy. Custom-made shoes fit your feet better, provide better support and are more comfortable. Because they wear better, they last longer. They will cost more, but you’ll have them for many more years. Just like a great bespoke-tailored suit.

Having said that, in some cases you’ll be fine getting a pair of shoes “off the rack”, especially if you have a fairly normal foot size and shape. Shoes are made on a “last” --- a shaped design of the human foot that serves as the template. The vast majority of people have fairly common feet, but there if you have unusually narrow or wide feet or shaped toes, you’ll be far more comfy in a custom pair of shoes made for you by a “cordwainer” --- that’s a chap who makes shoes by hand. You have to keep your piggies happy.


I’m hosting a party and I want it to be “Presidential” --- what were the favorite drinks of some of the U.S. Presidents?
– David in Manassas, VA

That’s an interesting hosting idea, David. It just so happens that in addition to being a master tailor, I am quite an expert on the Commanders in Chief.

Ever since George Washington distilled whiskey on his Virginia property (only about 30 miles from you, my friend), most of our Presidents have held a keen interest in spirited drinks. But while he liked a shot of whiskey now and again, Washington’s drink of choice on most occasions was something called Madeira, a “fortified wine produced on the Portuguese island of the same name.” According to historians, The Father of Our Country liked to down three glasses of it after dinner each night. Swell fella, that George.

James Monroe, our fifth President, caused a scandal when someone (wink, wink) in his administration bought 1,200 bottles of burgundy and champagne from France with money that was supposed to be used for furniture. Who needs a footstool when you can slam a bottle of bubbly instead? Several Presidents, including Andrew Jackson, Martin Van Buren, Zachary Taylor, Warren Harding, Dwight Eisenhower, and Lyndon Johnson, loved whiskey. But Andrew Johnson was noteworthy in that he drank so much of it that he arrived at his vice-presidential inauguration drunk.

Here are a few of the more noteworthy favorite drinks of Presidents that you may want to offer at your party:

McKinley’s Delight (William McKinley)
Mint Julip (Theodore Roosevelt)
The Coolidge Cooler (Calvin Coolidge)
Bermuda Rum Swizzle (Franklin Roosevelt)
Orange Blossom Special (Ronald Reagan)
Snakebite (Bill Clinton)

The current resident at 1600 Pennsylvania Avenue (Mr. Obama) likes to drink beer. So make sure to have some of that on tap too. JFK’s favorite was Heineken. Cheers!

Can I wear a pork pie hat with a bespoke suit?
– Jake in Bristol, VA

You can wear anything you want with a suit, the question is: will it look good? The pork pie hat is a great choice if you can pull it off. Currently it has a “hipster” connotation to it, so it looks best when worn on a man who has a beard or goatee, or maybe even a soul patch. Are you hip? By the way, did you know the pork pie hat was originally a hat worn by women? It wasn’t until the early 20th century that it became a men’s hat predominantly. If you need a pork pie or any other stylish hat for this summer, consider clicking over to Proper Topper, one of the best hat shops in D.C.

How many fittings does it take to get a bespoke suit made for me?
– Mike in Washington D.C.

Ideally it should take two fittings, but it may take as many as four. There’s the initial fitting where I get your measurements (a lot of standing up straight, tape measures, and good jokes), and then there’s the second fitting where we’ll adjust again to ensure a perfect fit. A suit should not drape or strangle, it should wrap comfortably around you like an envelope encases a perfectly-worded letter.

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