Men’s Trending Shoe Fashion: A Window to the Sole

When trying to express yourself through your style, shoes may not always be the first thing on your mind. Well, believe it or not, it’s one of the first things on a woman’s mind when she first meets you! Back in the day when my friends and I would be at a bar looking to meet guys, my one girlfriend would say, “If I don’t like his shoes, I’m out”. She swore she could pretty much figure out a guy’s personality the second she saw his shoes. Good looking, charming, wealthy, whatever it was, if he had a pair of shoes on that turned her off, she would run for the hills. What you put on your feet really does say a lot about you, whether it be your personality, grooming habits, status, or profession.

Researchers at the University of Kansas say that people can accurately judge 90 percent of a stranger’s personality simply by looking at the person’s shoes. “Shoes convey a thin but useful slice of information about their wearers,” the authors wrote in a study published in The Journal of Research in Personality (Volume 46, Issue 4). “Shoes serve a practical purpose, and also serve as nonverbal cues with symbolic messages. People tend to pay attention to the shoes they and others wear.” My girlfriends and I are always discussing women’s fashion, so I thought I’d conduct my own study and ask them what they thought about some popular men’s shoes and their personalities.


The summer iconic boat shoe was originally made for sailors and boaters to prevent them from slipping on the boat deck. I had to ask our very own Jackie Beard Robinson about these digs. First, because she’s a fashion icon and also because she has a boat she uses for travel. I don’t know anyone else who spends so much time hanging around docks, marinas and waterfront bars besides Jackie! “What can I say about the man who wears boat shoes? Since I’m married to a boater, I actually do love a man who wears them! Only if the dude wearing them is actually somehow associated with boats, then it’s COOL! If a guy wears boat shoes and is not a boater, he’s a total geek, stay away! The ultimate boater that wears the boat shoe is a strong, wise, in control type that lives his life around a lot of money, either his or people who have it. So in case you’re looking for a wealthy boater to spend time with, don’t poo-poo the boat shoe just yet!


Vans and other skate shoes have long been the essence of what some guys consider cool. If anyone is cool, it’s my long- time friend of over 25 years, Kris. She works as a State Manager of a winery in Napa and does lots of traveling and events, therefore around lots of men!

“So not that I see them as much lately, but guys wearing Vans make me think of high school in the 80’s. Back then; I was into guys who were “chill”, easygoing and low maintenance. But now as an adult, I’d assume he was still “way chill” and also “way lazy”! It wouldn’t surprise me if he were always arriving late to things, maybe because he still travels on his skateboard everywhere! He may still live at home with mom and is still a creature of the 80’s! Definitely not for me anymore!”


Flip-flops are undeniably comfortable! I can’t wait to get mine on the minute it reaches 70 degrees in New Jersey! But what about men wearing flip-flops? My girlfriend Laura works as a Director of Special Events for University Advancement and spends a lot of time on college campuses. Let’s see whether or not she thinks these puppies are a flip or flop.

“When I see a man out wearing flip flops I think he’s screaming, “I give up on society!” Unless he is directly within a few feet of a pool or lounging at home, he shouldn’t be wearing them. Not to mention having to look at men’s feet can be compared to watching a horror film. And don’t try to hide those monsters under socks please. Not a good look at all. My biggest pet peeve is when guys try to mix formal wear with beachwear. Flip flops should never be worn with a suit or jeans for that matter. They are practical but they have a place. Stay by the pool!”


It’s not every day we see men wearing a $900 pair of Ferragamos, but we do see men sporting other fancy footwork such as Gucci, Prada and Luis Vuitton. What do these shoes say to women about your confidence? For this one I consulted with my friend Anne, who is an Executive Director at a well-known pharmaceutical company. “My first impression would be he’s professional, makes money and most likely has everything he wants. He spends a lot of money on himself. I think if they are worn right and by the right person, they can be very sophisticated, sexy and shows confidence. But if a man is covered with designer logos that are in my face, I would probably think he was full of himself and most likely broke from spending so much money on material things.”


Reeboks have been around for a long time; I remember them back in high school. Mostly worn in black or white, they now come in a variety of colors. You may like your Reebok sneakers — and hey, that is fine with us. But just so you know, a lot of women don’t agree. I called on my girl Carolyn who is a Director of Strategic Marketing for a tech company where I imagine she works with some geeky guys, to hear her thoughts on this classic shoe. “If he wears Reeboks on the daily, he’s most likely nerdy and low maintenance — and has no swag and zero game. The worst is white reeboks with knee length denim shorts! He’s definitely not a gym rat because they are the farthest thing from athletic. The best is when they wear the black ones and they think they’re clever for choosing ‘semi-formal’ shoes that go with everything, but in reality, they look super tacky. It’s time to upgrade to Nike”


So here’s my favorite. When we think of Tims we think of work boots, and I believe there are two places for them – construction and gangster rap! But let’s not forget, Timberland makes so many different types of everyday rugged boots and shoes. I love a man wearing boots. Super sexy with a nice pair of designer jeans and or even with a casual suit. They can be dressed up or down. First words to come to my mind are ‘strong, masculine, hard worker, adventurous and swag’. This guy pays attention to detail!

So there you have it! There are so many other shoes out there but I just touched on a few. We really do notice what’s on your feet and don’t forget, women love to analyze everything! We spend hours picking out new shoes and taking care of our feet. Men should try to do the same! Remember, shoes may be the last and smallest detail in your mind when creating your style, but it’s the first thing on our minds when we meet you.

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