Shoes 101: A Man’s Guide to Footwear

The easiest way to ruin any outfit is to wear a terrible pair of shoes. In the same vein, the easiest way to spruce up an outfit is to wear a fabulous pair of shoes. There’s a reason women are obsessed with shoes, and it’s a shame so many guys don’t even consider shoes to be an integral part of their outfit.

If there’s one thing you should overspend on, it should be shoes. The reason for this is the ROI (for non-finance types this is Return on Investment). You may spend more, but you will get a far greater ROI on more expensive shoes than cheap ones because of longevity and comfort.

Trust me, I wore a pair of Aldos for a year, and at the end, I couldn’t wait to toss them out. Like when I engaged in an Olive Garden unlimited soup and salad eating contest with my eldest sister when I was 10 – NEVER AGAIN! But I digress.

Here’s a sweet and simple guide to the different types of men’s shoes!

Lace-Ups: Generally considered the most dressy kind of men’s shoe

Cap Toe: Perhaps the most popular type of shoe, it’s appropriate for almost all types of business or dressy situations.

Cap Toe

Wear with: Suits, dress pants

Wing-Tip: You can tell it’s a wing-tip because of the distinctive “W” shape in the stitching near the toe.


Wear with: Heavier fabrics like tweed and flannel

Plain-Toe Oxford: Probably my favorite of the dressy shoes because of the simplicity of the stitching, the plain-toe fantastic for almost all dressy settings.

Plain Toe Oxford

Wear with: Suits, dress pants

Monk strap: The buckle on the side is the distinctive feature. A man wearing these may gain a little panache.

Monk strap

Wear with: Suits, dress pants, jeans

Shoes without Laces: Generally considered less dressy than lace-ups, and the cheaper of the two options

Loafers: With roots in preppy traditions, the loafer is ubiquitous with khakis.


Wear with: Khakis, jeans

Slip-On: With the front of the shoe generally coming higher up the foot than the loafer, slip-ons look great with jeans.


Wear with: Dress pants, jeans

Drivers: My personal favorite in this category because they are SO COMFORTABLE. Seriously, it’s like wearing slippers in public. The sole is more casual (not wood). It’s called a driver because it lets you feel the pedals in a car better.


Wear with: Jeans, khakis, shorts


Boat Shoes (think Sperry’s)

Dress Boots (for colder weather conditions)

Shoes are an easy way to upgrade your style – you really should be spending upwards of $200 on a pair of shoes. I know it sounds like a lot, but it’s really worth it!

(Photocredits: KinoWear)

About Fab Manual

Men's Fashion Blogger
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