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Guys, you should always be comfortable in your own shoes. This is to be meant both literally and metaphorically. Choosing what shoes you wear may depend on your lifestyle, how you’re feeling on that particular day, or where you’re going. You may not always consider what you wear as having an effect on how someone perceives you to be as a person.

The style, color, and design of your shoes could potentially shape who you are and your personality makeup in the eyes of someone else. A first impression is always important, and if you’re meeting anyone for the first time, especially work clients, then consider the shoes you wear as a message to them, or a visual way of introducing yourself.

Here we’ll go through several men’s styles of shoes and what thoughts may pop up from an observer when you wear them.

Work Boot

Any type of work boot, whether it be Timberland Pro or Clarks boots, can express your All-American, workman style personality. Work boots are worn with a purpose, not always for style. When you’re lacing up some work boots, you have a job to do and it shows control and determination. Also, a level of rugged toughness can show from wearing these.

Running Shoes

Running shoes typically display an active lifestyle to the casual observer. They can show you as someone with contemporary tastes who also likes to stay light on his feet. Nike, Reebok, and New Balance are the main brands to look to.


For the guy who appreciates tradition and tailoring. Wearing these shoes will show you as someone who depends on the right type of shoe to complete his look for the day. Oxford shoes can also show you as someone who even during out-of-office hours likes to keep a well-kept edge and can easily transition from suit to rolled up jeans.


One key thing to keep in mind is the ends of your loafers. Say no to square toes! They are perceived as old fashioned and out of style. Buy loafers with rounded fronts.

Loafers are also good for showing both a professional yet causal side to yourself. Good with work and out of work attire, you can’t really go wrong with loafers from brands like Dansko Professional.

Flip Flops

Make no mistake about it, for men looking to make an impression, keep the flip flops at home. They belong on the beaches and boardwalks. Flip flops make you appear too laid back and perhaps set off a tone that you’re a slacker.


A style that is becoming more popular again, a set of clogs can be perfect for a relaxing, low key weekend. You’ll maintain a calm, comfortable look while enjoying the little things in life. However, clogs should be avoided in the office and at restaurants.

Double Monk

For a guy with great confidence in his step, the double monk strap is an excellent selection. The corporate young gun or the guy with something to prove will probably be wearing something similar to this.

Contrast Sole

Wearing a traditional shaped shoe with a contrasting color on the sole indicates a blend of confidence and personality. This guy like to have fun, stay on trend, and maintain a look that is office appropriate. It may say that you have something special and interesting to bring to the table.