How to Step Up Your Shoe Game (and Why It Matters)

men's shoes“You have brains in your head. You have feet in your shoes. You can steer yourself in any direction you choose. You’re on your own, and you know what you know. And you are the guy who’ll decide where to go.” — Dr. Seuss

I’ve been writing about some very serious things lately. So, I want to talk about something even more serious.

Shoes. And specifically, men’s shoe styles.

But first — what makes me qualified to be your style baron and navigator of sartorial waters?

Well, for one thing, in a previous life as a jetsetting twentysomething management consultant with a dangerous new source of disposable income and premature taste for the good life, I developed an obsession with men’s shoe styles and clothes. Sites, blogs, stores, brands — I was on top of everything #menswear. I established a bit of a reputation as a dandy in my office.

I also did it without breaking the bank, by doing a lot of research and shopping online, often from lesser-known new brands.

I’ve whittled down by wardrobe since then, but I still believe that dressing well — and appropriately — is important. It’s also teachable and learnable.

I’ll be doing roundups to simplify things, but my top recommendations for resources are Put This On (for frequent posts covering a wide range of topics + periodic guides), StyleForum (for a huge community of knowledgeable and usually friendly stylish dudes), and Valet (for a slightly trendier and more product-based site but with good advice and recommendations). Antonio from Real Men Real Style also frequently posts great overviews and guides at The Art of Manliness, which are very helpful and informative.

Style? Don’t You Mean Fashion?

I differentiate style from fashion. Style is eternal and personal, whereas fashion is trend-driven and often powered by groupthink. It’s a topic worth its own discussion, but the main point is that certain items of clothes and shoes looked good 50 years ago and will look good 50 years from now. (Think James Bond’s tailored suits or Marlon Brando’s white tee getups.)

My personal philosophy has shifted from caring too much to wearing what’s comfortable, fits well, and works for me, so I can worry about more important things. In addition to my Chipotle routine, I have a Doug Funnie-esque uniform to keep me focused on the important things. Hanes white pocket tees, alternating beat-up raw denim and black Levi’s jeans, and boots or white sneakers, depending on the weather.

Why Shoes?

They may comprise a proportionally small component of your overall appearance, but they are worth putting extra time (and money) into. Multiple studies have found that we make judgements about people based on their shoes, and I’ve found this to be the case as well. Especially when it comes to making a good impression on women.

If I told you I went on a date with a girl once who told me she gave me her number only because she liked my shoes, would you believe me? (You should, as much as I’d like to think it was my acerbic wit and irresistible charm, though clearly they go together.)

Shoes should be chosen appropriately for the situation. Wearing running shoes to a first date or your unpolished beat-up “dress shoes” to a serious job interview? I totally agree that it should be you that your date or employer is evaluating and not what you wear, but expect to be taken as seriously as you take your appearance. To me, it goes beyond the superficial: What you wear is an element of your personal taste. The choices you make about your appearance reflect how you value (or don’t) the occasion at hand.

In addition to their aesthetic, your shoes are also the most functional piece of clothing you’ll wear, as you spend most of your day on your feet. I can’t count how many bros I saw wearing socks and boat shoes in the middle of Chicago winters, imagining how uncomfortable that would be. The right pair of shoes for the right weather and/or situation could mean the difference between a pleasant day and a painful one.

Men’s shoe styles are also an investment — higher quality well-made shoes might be more expensive upfront but pay for themselves in the future. For example, a $200 pair of dress shoes that can be resoled for $40 a year (while developing patina and a story) are cheaper in the long-run than buying a new pair of ugly, crappy shoes for $90 that wear down and need to be replaced once a year.

On that note, the internet has opened up the door for direct-to-consumer niche men’s footwear brands to sell very well made shoes at lower than retail prices. I’ve rounded up as many of these (and more common) brands in a list of recommendations to step up your shoe game.

  1. These boots were made for walking.

The first purchase I made with my signing bonus and before moving to Chicago was a pair of Wolverine 1000 mile boots. They’ve seen way more than a thousand miles and have traveled with me around the world. Great shoes, but pretty expensive and a bit clunky/clowny in shape as they stretch and age.

My buddy and his friend started Thursday Boot Company and I couldn’t recommend a pair of boots more highly. I went for the Captain in black myself and get compliments on them everywhere I go. Nope, I’m not getting a cut for recommending them, but I love that two young entrepreneurs were able to create a beautiful, well-made, durable and stylish boot for under $200. (Look through their Kickstarter for a lesson on how to kick ass and take names.)

If you’ve never worn boots before, prepare to feel a new level of badassery and manliness you never imagined possible before. Initially rigid and uncomfortable, they will eventually shape to your feet and ankles and protect you from both the elements and looking basic.

  1. Crush the snow with style.

Leather boots are perfect for chilly weather and lighter rain, but for serious snow or precipitation, you’ll want something right for the occasion.

LL Bean duck boots were a vintage prep staple and kind of “had their moment” a few years ago, but will pretty much make you amphibious and seek out puddles like an adolescent. Sorel boots — on the more expensive end — keep your feet toasty and dry while looking good as well.

If you work at an office where dress shoes are required, consider bringing them separately from your snow shoes to change into, or wearing galoshes. Essentially condoms for your dress shoes, galoshes slip on and off can be put away after you arrive in style.

  1. Not all dress shoes were created equally.

I bet that you, like me, separated your tiny college closet into a pile of sneakers, a pile of flip flops, and a pair of “dress shoes” that looked like a duck-billed platypus that just completed a Tough Mudder.

Remember when I said that style is subjective? The only thing I will not compromise on are square-toed shoes. Don’t do it. Please, just don’t.

A brand that makes really well made and good looking men’s dress shoes that won’t break the bank is Jack Erwin. Easy shipping and returns makes buying them online possible.

For an all-around dress shoes that will work with pretty much every color suit, you can’t go wrong with a black cap-toe oxford. If you’re looking for something a little more dashing and wear more grey and navy (because black is for evening weddings and funerals), consider a burgundy medallion-toe or brown wingtip.

If you have to try on a shoe in person to buy it, Allen Edmonds is a great made in the USA brand that makes a lot of classic styles at decent prices. I recommend the Park Avenue and Strand shoes, which are often on-sale at Nordstrom and can be found for much cheaper new or used on eBay.

  1. Flip flops are a flop.

That’s a good start for your dress/formal shoe game, but what about the more casual side of things?

Flip flops make perfect sense when you’re on the beach or by the pool. But the inconvenient truth is that nobody wants to see your hairy toes and untrimmed nails anywhere else.

There’s a lot more room for personal taste here, depending on the look you are going for, but I’m a fan of timeless sneakers that look better with age. From basic white chucks to OG Vans, I prefer simpler styles. The cool kids wear Common Projects, glorified white sneakers with pretentious gold numbers. Kent Wang is an online boutique that makes a similar version for much cheaper.

Desert boots are another classic, simple, and comfortable way to up your style. They’re also a great date shoe if you feel uncomfortable in dressier shoes. Be forewarned: They are pretty common at this point, and despite the “boot” moniker, the “desert” part means they were not exactly engineered for inclement weather.

Penny loafers are another vintage prep staple that are comfortable and classy and make life easy with no laces. Bass makes the classic “Weejun” and pretty much every other shoe brand makes a version as well. Rubber soles will tend to be more comfortable and less durable, whereas leather soles are dressier and longer-lasting.

  1. Whatever you choose, take care.

Seriously. If you’re going to up your shoe game, you have to up your shoe care game as well. Consider it part of your manly routine of self-maintenance and self-discipline.

If you wear dress shoes, alternate them every day and put cedar shoe trees when they’re warming up in the bullpen for their next appearance. Also, polish them at least semi-regularly, and condition the leather once in a while. Soles eventually do wear out, but the wonderful thing about a well made goodyear welted dress shoe is that a decent cobbler can replace the sole for you, and ta-dah! Like a new pair of shoes. For significantly cheaper.

Lastly, your budget might not allow you to go out and spend much on shoes, but consider the benefits and explore ways to find great shoes at better prices. I personally feel iffy about buying used shoes, but you can stumble across some great pairs, and there’s a huge online marketplace for cheaper unworn shoes and factory seconds.

Regardless of what you chose to buy or wear, remember — people do notice your shoes. If you’re developing into a well-rounded charming rockstar, why not step up your shoe game as well?

How do you feel about the importance of footwear? Are there any shoes/brands we left out? Are there any on the list you really like, or would you like more suggestions? Drop a comment below, and share your own thoughts about men’s shoe styles!


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