The Dictionary of Men’s Shoes: How Shoes Can Make You More Attractive As A Man


I woke up this morning with that “Started from the Bottom” Drake song in my head, so this seems like an appropriate place to start deconstructing men’s fashion. And since we’ve already got a Dictionary of Heels at Designer Swap, why not have a Dictionary of Men’s Shoes? I was pretty shocked to find that the whole men’s shoe situation is very complicated and layered, like an onion. I can see why men get so confused and end up in mandles and whatnot. Here’s a dictionary so that you know the terms, but before that: a couple guidelines to steer you clear of shoe disaster. I asked Matt Allinson, writer for popular UK men’s fashion blog Fashion Beans, for the non-negotiables when it comes to shoes. His reply? “Don’t ever wear square-toed shoes, and always match your shoes to your belt!”


Rule #43 from A Fine Young Gentleman: “It is impossible for a man to be considered well dressed if his shoes are in poor taste or of noticeably poor quality. For any good ensemble is built on a fine pair of shoes.”

Formal shoes:
• Choose black calf leather oxfords with plain or cap-toes.
• Avoid broguing/wingtips and slip-ons like loafers.
• Never wear square-toed shoes.

Everyday shoes:
• Brown shoes are much more versatile than black because they can easily be dressed up or down (black is always somewhat formal and stark). Brown shoes also go with nearly everything – except black pants. Go for dark brown if you want to be stylish but safe, or oxblood if you’re more adventurous (oxblood also goes with nearly everything).
• White is an appropriate and desirable colour for sneakers but pretty out there when it comes to leather shoes.
• Unless you’re super colour-savvy and ready to spend some money on several pairs of shoes, stick to the basic shades. This rule does NOT apply to suede shoes, which are very casual and are acceptable in a variety of colours.
• Match the shade of your shoes with those of your belt and watchband. Don’t worry about matching with your wallet and bag.
• Taps, soles, heels and heel pads need to be replaced periodically if you want your shoes to last.
• Consider buying cedar shoetrees to preserve the shape of your shoes, prevent creasing, and absorb moisture.
• Never wear square-toed shoes.

Winter shoes:
• Your socks are your chance to show some major personality, so rock bright socks for when your pant leg rides up to show some ankle. Don’t be boring!
• Never wear square-toed shoes.

Summer shoes:
• Go without socks and put talc powder in your shoes before starting your day to absorb sweat/avoid smelliness. If you’re not comfortable skipping socks, buy some loafer socks.
• During the summer, you may want to experiment with coloured suede shoes, or even bright trainers. If you’re wary of colour, stick to white Plimsolls.
• Did I mention never to wear square-toed shoes?


Images courtesy of:, Ask Andy About Clothes, Oxford Etc., A Headlong Dive, Arden Reed, DeoVeritas, The Shoe Buff, jobtrakr, The Art of Manliness, ctshirts, Comptoir des Espadrilles, Selectism, GQ Magazine, Englin’s Fine Footwear, Blankmode, Sperry Top-Sider, L.L. Bean, Pelle Line, Lyst, highsnobiety, The Hut, High Top Supra Shoes, Lost in a Supermarket, This is my so-called style, fashionsupdate, fashionbeans, graziadaily, jrpwesternproducts, flopstore, birkenstocksuk, Bottom of the Swamp, o2gearshop

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6 Responses

  1. Karen Chow's Boyfriend

    I would suggest men spend a bit more when it comes to more formal shoes as the leather will wear nicely and last you a lifetime so long as you resole. Some good mid end affordable brands to consider: Church’s, Alden, Allen Edmonds, Trickers

  2. From a woman’s perspective. My faves have got to be wingtips, hiking/brogue boots and sneakers. I love a man who can pull off some classy wing tips during the day and some sneakers at night. My kind of man. Great post Caley!

  3. I think Sneakers are totally underrated and require further discussion and expansion on the topic. But I agree with Karen Chow’s Boyfriend, the better quality leather the longer they will last. Camper has some nice leathers with wicked designs.

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