Piece by Piece: Rocking the Saddle Shoes
We know how tough saddle shoes are. Believe us. Pulling them off isn’t easy. But then again, maybe it is…
The thing about saddle shoes is they look like golf shoes. Plain and simple, they look like golf shoes. And no one acknowledges it!
That makes wearing them a tough thing to do because only golfers want to look like golfers. Unless you’re talking about the style of Chi Chi Rodriguez, the style of any golfer is usually a subject of mockery. The wise Happy Gilmore once said, “Golf requires goofy pants and a fat ass.”
But let’s talk saddle shoes. These things are absolute classics. And they’re hip again. So how can you pull them off? They’re pretty tough to do with something like a formal suit or a tee shirt and jeans because they tend to really stick out. The truth is, in order to get the shoes to blend in a little more, you have to pay homage to the preppy origins of saddle shoes in the rest of your outfit. In other words, these are preppy kicks, so help them blend in by donning more preppy garb. Think of it this way: the Incredible Hulk would not stick out if he were surrounded by green people. So overtly preppy stuff sticks out less when it’s surrounded by other fairly preppy stuff.
But resist the urge to look like a southern lawyer. The seersucker suit and saddle shoes thing is certainly a tradition we respect, but unless you’re actually in the South, throwing that outfit on is a little contrived, a bit old-mannish, perhaps a tad dated. The real trick to saddle shoes is not to put them in the context of an outfit with the influences of a rural prep, but to keep them hip by throwing them into the context of an outfit with the influences of a city prep. Those saddle shoes will look awesome when you prepily urbanize them.
So here’s what it takes. First, get saddle shoes with rubber soles because you’re roaming the streets. Plus, the red rubber just looks cool and makes it clear that you don’t have golf cleats on the sole. And if you trust us on this, Bass has the pair for you.
Then add some preppy influence with a gorgeous seersucker shirt by J. Lindeberg that’s made to fit in a hip way (so it’s city-safe), and finally, pop on some slim chinos by Rugby. Their University Chino is killer. The fit’s slim, so be careful with your sizing, but they’ve got that great tapered leg that harkens to the pics you see in Take Ivy. Roll the cuff up a tad and you’re ready to kill it. And notice… no socks. It’s summer, and we’re updating saddle shoes.
Shirt, $108.50 at Confederacy
Chinos, $69.50 at Rugby
Saddle Shoes, $89 at Bass




I know you seem to love Bass shoes, and they’re definitely affordable enough, but how can you continue to recommend them when they’re so shoddily constructed and lack refinement in design? Really, they’re terribly chunky and have a bulbous toe. I’d rather spend twice as much, get something well designed and constructed, that would last me three times as long.