Dress Like a Man: Shoes

January 9, 2017
2 mins read

“When I was a child, I spoke like a child, I thought like a child, I reasoned like a child. When I became a man, I gave up childish ways.”
A Man of the West should dress like a man.
Over the next month, I will help you start doing that.
You don’t need to spend a lot of money to dress like a man. You don’t need to wear suits every day to dress like a man. You don’t need to wear uncomfortable clothes to dress like a man. You should wear clothes that fit well and enhance your appearance.
This guide is for a business casual environment–if you follow my recommendations, you will look better and feel better at the office, at church, and around town.
The first week in this series addresses an area that most men think very little about–shoes. This is your opportunity to up your game with very little effort and separate yourself from everyone else at your office.
The first step in dressing like a man is wearing leather shoes to the office. Keep the tennis shoes and sandals at home.
You should have at least two pairs of dress shoes so that you can alternate–this is not about wearing something different as much as it is about making your shoes last longer. You should generally give your shoes a full day in between wears so that the leather recovers.
Here are three suggestions–pick two of them (or all three) and you’ll be set. While these are not going to be shoes that last for ten years, they are without a doubt the highest quality shoes at their price point and probably an upgrade over what you’re currently wearing to work.

JCP Logan Wingtip
JCP Logan Wingtip

This wingtip is from the JC Penny Stafford house brand. It only comes in the light brown shown above.
I’ve owned this shoe for two years and worn it at least once a week–it’s held up remarkably well for the price.
As with almost every item in these guides, ignore the MSRP–retail stores are constantly having sales. This shoe is frequently available under $60 or lower–several times down around $40. It’s a great deal if you get it for $60 or less.
JCP Gunner Captoe Boot
JCP Gunner Captoe Boot

JCP Deacon Wingtip Boot
JCP Deacon Wingtip Boot

Dress boots work incredibly well for business casual, and are more versatile than dress shoes. Both boots are available in black and light brown. My suggestion is to get the captoe boot in black and the wingtip boot in brown–this gives you a more formal pair of black shoes than you can wear to somber events like a funeral. I recently acquired a pair of each and they are very comfortable out of the box.
Like the dress shoe, you can regularly find them on sale for $60 or less. They’re a great value at that price.
All three shoes featured can be worn with jeans, chinos, wool trousers, or even a suit. Just remember to buy at least two of them, alternate wears, clean and polish them regularly, and you won’t have to worry about shoes for several years.
For more in-depth reviews of these shoes:


  1. Those examples aren’t proper shoes, I’m afraid.
    Any chap worth his salt knows that shoes are sartorial priorities and thus great care (and shekels) must be expended in choosing a quality pair.
    For a good American brand, try Alden shoes. Choose a solid oxford, derby, or loafer. If you’re a cost-conscious gent, note that Alden frequently email lists of ‘seconds’ at lower, more affordable prices. Allen Edmonds is another reputable US shoe company.
    Moving up the shoe pyramid, one encounters the English makers. Among these, Crockett & Jones, Alfred Sargent, and Church’s are my favourites. Better quality, improved design. Some good websites for English shoes:
    Are you ready to go bespoke? Let me know if you’re at that point and I can give you some tips.
    When choosing classic footwear, remember to keep it simple, keep it classic. Avoid fancy designs and colours, at least at first. Once you’ve mastered the basics, you can branch out and experiment.
    Leather souls > rubber souls
    Goodyear welted construction > Blake stitching
    Shoes are quite literally the foundation of any distinguished gent’s wardrobe, so take care in choosing a proper pair.
    Good luck!

  2. Good to see this topic brought up. Proper footwear for the job/activity seems like a lost concept lately.

  3. I will always be a jeans & t-shirt kind of guy. I wear sneakers or running shoes with them and that is my daily work uniform. It’s not a problem to switch to colarred shirts and slacks at a moments notice and I have some dress shoes (Merrills for example) that are a step up. And a suit plus dress shoes if a big client or VIP will be on site.
    But daily wear? Neat and clean Puma running shoes and brand new jeans. I wipe the shoes down regularly so they are bright and I don’t wear faded jeans. Also my tshirts are new and no holes or tears. I’m neat and clean if simple.

  4. Something else too about this style of men’s footwear is that if you take good care of the leather like the article says, the shoes can be re-soled by any good shoe repair shop owner, and be perfectly good looking for several more years. My father had wide feet, and he always swore by these shoes. They are classic and they do look nice.
    Some professions are better suited to the jeans, sneakers and t-shirts, but it never hurts to know when to dress appropriately. There is nothing gamma about dressing properly when the occasion calls for it. It is called respect.

    • In our private conversations, we have much discussion about the superiority of boots. Just to show that we have varying opinions around here.

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