I know, I just said I love a man in flip-floppies but there’s some nuance to my taste in men’s shoes.

Let me explain to you the types of shoes women are talking about when they say they judge a man by his shoes.

Doc Martens

There is nothing in this world that is sexier than a man in Doc Martens.  I suppose the brand isn’t important but I like boots more the more they resemble docs.  Docs are an awesome shoe and they have to be shown-off for the full effect.  There are two ways to wear docs.  I will accept no other boot/pant styling.

Pants tucked into the boot.  Preferably with skinny pants so it’s a seamless line but I’ve seen it done well with baggier pants.

With cuffed pants.  This style works better if you carry weight on your legs or wear a baggier pant.

Both styles send a shiver up my spine and if I were a fascist dictator all men would have to wear this combo daily.



If I were a guy these would be my go-to shoes.  Chukkahs are really attractive because they’re so thin and have such a simple cut to them they look casual but they’re so tailored and often they come in either leather or suede  so they also look like you put effort into your appearance.  They’re an easy casual shoe that look great with either slacks or jeans.

Double Monks

Double monks are the king of dress shoes.  They are hands down the most stylish formal shoe available.  The wrap around style keeps them slender and they don’t look like clown shoes which is always the worry with men’s dress shoes.  The wrap around feature also makes them look really polished and elegant.  Like docs I think they also should be shown-off and they look great with a cuffed pant.

Sleek Sneakers

Atheist Shoes Berlin

Chucks, Asic Tigers, Atheist shoes all have this sleek, narrow look to them that is so elegant.  These are sneakers that you could wear with a suit.  They’re very simple but they look a thousand times better than any other men’s sneaker because they have an elegant silhouette.

Boat Shoes

Boat shoes scream old money.  They make any outfit look really preppy but when the preppy look is done well, boat shoes look awesome on men.  They’re slip on shoes that make you look like you own a yacht.  What more do you need?!  Boat shoes are like the cheat code to classing up a casual outfit.