Choosing The Right Footwear


Men being men, we tend to see shoes as utilitarian, something we need, but not something on which to spend a lot of time. Once we have to look good though – an interview for the top job, a friend’s wedding, or a big date, we’re scrutinizing our footwear like a panicked drill sergeant. Though men need different kinds of shoes for different reasons, too often we just default to the three or four pair (at the most) which have been in the closet for years. The outcome isn’t always pretty.

This is a sad situation because if most men took the time to understand how well-made shoes are manufactured, they would pay much more attention to their feet. The quality of materials, complexity of construction, and sheer amount of time it takes to make just one pair ensures that a truly well-made pair of shoes lasts for many years. Not only that, but there is an awful lot of truth to the saying that women judge a man by his shoes.  To be “well heeled” means that you have money and class. Or least you have a solid income and can afford to keep you shoes in good condition. Simple things like keeping them polished and replacing your soles and heels before they wear away all together will help your footwear age gracefully and make you look good.

Men’s shoes have two distinct advantages over women’s. First, as my wife tells me on a regular basis, men’s shoes are actually designed to fit. A properly fitted pair of dress shoes should be comfortable all day long. Second, men’s shoes are built to last. I still have a pair of brown wingtips that were a present from my father 17 years ago. I have re-soled numerous times and that has helped them age beautifully.

With more men actually focusing on dressing well, too many still fall into the “not-appropriate trap.” Generally, this is when incompatible clothes are thrown together under the delusion that simply mixing business and casual clothes creates “business casual.” It doesn’t. The problem often arises because a lot of guys know either how to dress casually or dress up but nothing much in between. An annoying offense I regularly see is wearing very formal cap toed oxfords with casual, heavy cotton khakis. It looks ridiculous and draws unwanted attention to an awkward looking outfit.

When getting dressed in the morning, you need to pay attention to things like scale, material, texture and balance. When dealing with footwear, you also have to consider function – what are you doing and where are you going? Should I wear my good interview shoes with cargo pants so they look more dressed up? No. With dressy jeans, yes; that is very sharp look that Europeans tend to pull off a bit more successfully than most Americans.

When it comes to purchasing a pair of shoes, keep one thing in mind: it’s not like buying a book or a pack of undershirts. Shoes are to your feet what tires are to your car. What they’re made of and how they’re put together have a lot to do with how they look, perform, and last. With men’s footwear, you really do get what you pay for, and with dress shoes, that comes down to materials and construction.

If you are lucky enough to be the President of the United States or the Prince of Wales, your shoes are made entirely by hand, fit like a glove, took months to create and cost a fortune. Makers like John Lobb and Edward Green create veritable works of form fitting art with prices that look more like mortgage payments, but they also offer ready to wear lines that are a little more in reach.

I’m not saying that the only shoes you should own must be custom or bench made. Different people have different needs and budgets. Take a look at what you wear and think about how you want to present yourself to the world. From formal occasions to day-to-day work needs, to washing the car, buy the best you can afford. As with tailored clothing, it’s better to have fewer well made pieces than a closet full of junk.

When it comes to figuring out what shoes to wear at any given time, try using common sense. For heavier, more casual pants, you want a larger overall profile to balance out the heft of the fabric. This means a thicker sole, less refined stitching, and an overall sense of casual, but not sloppy, style. A less glossy finish also gives the shoe a less formal feel.

Leave the proper oxfords, cap toes, and balmorals for your suits. Bluchers and loafers can be worn with dress pants that have a finer hand and “dressy” khakis. I’m also a big fan of having at least one pair of suede dress shoes, slip-ins, or ankle boots. They go with anything and lend an air of sophistication to whatever you have on. In a rich, dark chocolate, they pull together casually dressy outfits like nothing else really can.


Chris Hogan, an association executive based in Washington, D.C., blogs at A lifelong interest in style and clothing led to sales and management positions at several Ralph Lauren stores and an active wardrobe consulting practice


  1. Do you have any pictures of the outfits matched to the shoes you are describing that you could potentially email or share?

  2. Hi Brad – very sorry for taking so long to get back to you. I will track down some related photos and post them on shortly. Please let me know if you have any othe questions.