Trends come and trends go and sometimes, like an unwanted house guest, they just never leave.

Sometime in the mid 90’s the square toe shoe arrived and never left. Pushed by designers like Steve Madden, Stacy Adams and pretty much every major shoe brand they became an American footwear staple.

To be honest the square toe can’t even be considered a trend at this point. Just an abhorrent style choice.

Along with the dri fit polo and baggy pleated pants , the square toe completes the unholy trinity that is the casual office drone uniform.

Listen, i’m not here to virtue signal. I wore square toes for the better part of a decade! And I thought I looked damn good doing it too. Man was I wrong, we were all wrong. Very wrong.

Hell some of us are still wearing them. Just look at this beauty over here at Macy’s. Five star reviews across the board! Claiming the compliments never end. Sorry fellas aunt Doris  doesn’t count.

I get it. They’re simple, they’re comfortable and they’re convenient. But the honest truth is that they’re downright atrocious.

I mean for the love of God just look at them! If shoes are the first thing a woman notices about you then is that what you really want them to see?!

Don’t lose hope.  We just need to step outside of our podiatry “safe space” and follow in the footsteps of the Gent. Salvation awaits my brothers!

Time to throw your Steve maddens in the donation bin and try these upgraded alternatives.

Notice: Buying via our links may result in us getting a commission

The Modern Penny Loafer

This is definitely not your dads penny loafer. These modern versions are sleek and sexy while still giving you the convenience that you get with a slip on. Which is one of the reasons why guys purchase the square toe over and over again.

The penny will be a workhorse office shoe as it can be worn with the chino sportcoat combo on Thursday and with jeans on a casual friday.

The Monk Strap

The Monk Strap has exploded in popularity over the last few years and for good reason. Again you’re getting the convenience of a slip on but with a sleek aesthetic upgrade. Opt for a double or single strap (see below). These go great with a suited look and can be worn casually as well.

 The Driving Loafer

Whether you’re channeling  your inner Italian playboy as you hit the streets in your  Maserati or spilling coffee on your favorite shirt while the IT guy bricks your PC the Driver is a prime choice.

Originally used as a functional shoe for yes…driving these loafers crossed over into mainstream footwear decades ago. These could easily go from casual Friday to a Sunday BBQ.

What are you favorite alternatives to the square toe abomination? Leave a comment below. Let’s talk!