What a millionaire’s shoes say about him

designer shoesMillionaire men can be difficult to read. It’s tough to get a sense of who they are at a glance because there’s often so much fanciness and fluff surrounding them. Did he make your super romantic date plans or did his assistant? Is eating at this well reviewed restaurant a special sign or just where he goes on Mondays? Is he dressed up or always wearing a suit? Well, after years of working with millionaire men, I’ve picked up some ways to make snap judgments about them. And I’m well aware of the adage “You can’t judge a book by its cover.” I just don’t agree with it. How else are you supposed to judge a book? Why does so much work go into the cover art? How come books that are faced out on the shelf are so much more appealing to me than the ones that are spine out? Because you’ve got to judge a book on its cover! It’s the only way. Here are some judgments I’ve found to be true about a millionaire man based on his footwear!

Designer sneakers

Here’s a guy who wasn’t cool or fashionable in high school, came into a lot of money and now wants everyone to know it. He probably also wears man jewelry and introduces himself by his title at his company. Nothing about this is necessarily bad. It’s just that he’s a bit insecure and you should know that going it. You might need to build him up a bit to get him feeling comfortable enough to let his walls down and truly be himself.

Regular sneaks

Here’s a guy who’s confident in his abilities in his career and knows he doesn’t need to work overtime to impress anyone. He’s just impressive. I also think it means that he’s careful with his money and won’t ever overspend to impress you. So, even though he’s a millionaire, don’t expect the five star treatment on your first date. There may be some subtle cockiness that comes across the first few times you meet him. Try not to let it turn you off. It should dissipate after a short while.


First off, boots might just mean the guy is short and hoping to get an extra inch or two. If that’s not the case, boots are an indication of sensibility and practicality. They’re sturdy and able to transition from work to weekend easily. It means he’s no nonsense and likes to keep things as simple as possible, while still looking dapper. These are my favorite of the bunch.


Loafers are for pretty boys or guys who think they’re pretty boys. They indicate a man who’s precious about his appearance and cares about the superficial in a big way. Not definite deal breakers, but dig and make sure you get to the core of his personality and aren’t just wooed by his flash and looks. Or, if you are just into his flash and looks, don’t let yourself get in too deep with him. Just have fun and find yourself someone you connect with on a better level when you’re ready.


Gross. Run, do not walk, away from this guy. If he shows up to the office or a first date in flip flops, just get out. It means that he doesn’t take you, his job or himself seriously. No one wants to see those stanky feet! If you two aren’t on the beach, sandals mean sayonara.

Hope you find this field guide helpful when you run into a millionaire man in the wild!