Top 5 Styley-Casual Shoes for Men.

There’s what men think impresses women, and there’s what actually impresses women.

It’s worth paying attention to this; some things, men worry about unnecessarily. And other things, men forget to pay attention to.

In a recent interview with a very talented SF style-genius, there was a lot of good news for normal, non-superhot guys:

“Shoes. Shoes are very important. A guy can have a belly, he can be sort of so-so looking, but if he smells good and has great shoes, game on. We can totally make something work.”

So the good news is you don’t need mega-lottery genes. Just like the caveman dorks who defeated the alpha-males through using their higher brain functions, you can make a smart shoe choice that might earn you a genetic legacy.

The “bad news”: there are no “Whateva Whateva shoes.”

Shoes always count.


What do you wear when you want something comfortable. Casual. That won’t call attention to your feet. That you can wear with a t-shirt or with a blazer?

One of these five. I list them below with level-up options for extra flair. (For a deeper dive on how to avoid too much flair, click here.)

Before you feast your eyes, some food for thought: every casual shoe below looks pretty much the way it has since it first emerged – 40, 50, or 60 years ago. The update is in the material and the color. This means that the best outfits to wear with your new kicks follow the same rules.


1. Chuck Taylor All-Stars: white, black, or blue.

+1 Flair: leather or herringbone.

2. Clarks’ Original Desert Boots: Beeswax Leather

+1 Flair: blue canvas

3.  PF-Flyers

+1 Flair: PF-FLyers Ebbets Field from Brooklyn Circus

4. Adidas Originals Superstar 2

+1 Flair for sticking to all white. But if you gotta get your flair on, keep it simple and pick one. Red. Blue. Black.

5. Pro-Keds by J. Crew

Perfect as is.

Perfect as is.

+1 Flair: Keep it simple, keep it white.

6. Boat Shoes: brown or blue

+1 Flair: Really blue. Or blue linen.

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20 comments

      1. For real. I was surprised at getting compliments from women on my adidas. I didn’t think they were the kind of shoes anyone would notice, I just bought them because I liked them and found a good deal.

        Liked by 1 person

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