If The Shoe Fits

The author two years ago, with 37 pairs of shoes and what turned out to be an incredibly disappointing beard.

A reader named Matt left the following comment on an entry of mine a while back:

"Hey there, love the blog. I've looked through, and haven't seen any posts specifically related to your views on men's shoes. I'm trying to "grow up" my shoe collection, but there's lots of styles, and was wondering about how different styles of shoe can apply to different situations. Any thoughts?"


Good callout, Matt, and thanks for reading. I'm a full-blown footwear fanatic and will be the first to say that your shoe collection is incredibly important; a good pair of shoes will make you look like a million bucks while a bad pair will make you look more like, say, thirty-five.

Most people have to answer this question at some point in their lives when it comes to their footwear: black or brown? We all pledge our allegiance to one or the other at some point, and you have to decide for yourself which camp you fall into. This isn't to say that you can only own one or the other, but it does mean that most people gravitate to one side in general. I, for one, love brown shoes because brown shows off the character of the leather in a more handsome way than black, and I own quite a few in every shade ranging from light, orangey tans for summer to ultra-dark brown suedes for winter. Sure, I own a few black pairs, but these only see action once every two months or so. Keep my bias in mind as you read through the following list.

Without further ado, here's a list of a few pairs you can get by on for the rest of your life and not have to worry. Everything else is gravy from here:

• Black oxfords: They should have minimal ornamentation like perforations, seams, wingtips, etc. You need a shoe that you can wear to a job interview, funeral, or some other event that requires seriousness on your part, and this is it. Pair them with your grey or black slacks or suits and make sure they're leather-soled.
• Brown dress shoes: Try a medium shade, like a tobacco color. you can wear it all year round and it looks excellent with blue, grey, and tan suits or dress pants. Try a wingtip, cap-toe, or dress loafer to start, also with a leather sole.
• Brown casual shoes: These can be a rubber-soled slip-on or lace-up in whatever shade you like. Get a couple of different shades and styles so you can rotate them and not wear them out too quickly and throw them on with jeans or your khakis.
• Boat shoes: These are great for sockless wear in the warm weather and are a great chance to throw some color into your shoe collection. Find a pair in blue, red, green, cream, brown, or whatever you like that's available. Wear them with lightweight cotton pants or shorts in the summertime.
• Non-athletic sneakers: No Nike Shox and no New Balances, I don't care what J.Crew is offering. You can get a streamlined "sport-inspired" sneaker at very low cost if you look in the right places. Wear these with jeans when you're hung over at brunch on a Sunday.
• Snow boots: It sucks when your feet get cold and wet, no matter how grown up you are.

Like the rest of your wardrobe, take your time in building your shoe collection. There's a lot to learn about what you like and don't like: lasts (shoespeak for "silhouettes") that you like, styles that make your foot feel either great or uncomfortable, and how to build a shoe collection that syncs with the rest of your clothing. Own your style and don't be afraid to take a risk here and there. There's nothing more grown up about that.

Oh, and remember that while some shoes look good beaten up, oftentimes it just looks slovenly. A shoe shine kit is a man's best friend.