The 5 worst shoe mistakes men make (and what Italian shoes you should wear instead)


Recently Esquire “named and shamed” five god-awful shoe style mistakes we see men make way too often. They have a good point: shoes play an integral role in your first impressions, so it’s important to get it right. Whether the mistake is sloppy or just stylistically challenged, we have some alternative ideas for Italian shoes that are sure to correct it.


Mistake #1: Flip-flops and jeans

We have our reservations about flip-flops, but since there is a time and a place for them (aaaahh the beaches of Rio!), we will hold off on over-generalizing our criticism. However, trying to pass these skimpy sandals as acceptable casual wear in the city is inexcusable.


Italian shoe solution: The McQueen Driving Shoe

If you want comfort in your casual look, go with a soft slip-on like our McQueen Driving Shoe. They’re perfect for slipping on when you’re on the go and with their reinforced arch, they’ll do your back more favors than any pair of thongs could. Get your pair here.



Mistake #2: Unlaced Combat Boots

This is a perfect example of a trend whose time has come and definitely gone. The look is a paradox; how can something be both sloppy AND try too hard?


Italian shoe solution: The Newman Chukka Boot

Trade the sloppy for the sophisticated. With a sparse two grommets, there’s no excuse to go unlaced in the Chukka. These boots aren’t just a trend; they’re a style staple that will have a happy home in your closet for years to come. Get your pair here.



Mistake #3: The Running Shoe and Suit

This isn’t just a mistake; it’s a downright sin. No amount of comfort is worth ruining the look of a suit with shoes that are made for one specific purpose. They are running shoes. They are for running. Nothing else.


Italian shoe solution: The Cagney Cap-Toe Oxford

If you’re wearing a suit, you need to be wearing leather shoes. If you’re unsure which style of leather shoes you should be wearing, you can never go wrong with an Oxford. The cap-toe Oxford is a classic choice that will last season after season. Get your pair here.



Mistake #4: The Square Toed Loafer

Remember how people dressed in 2003? Don’t do that anymore. Square toes are unflattering and dated. Donate them, throw them out, or burn them for all we care… just avoid being square…toed.


Italian shoe solution: The Stewart Penny Loafer

If you want to wear a loafer, there’s no style more timeless than the penny loafer. Popular since the 1940s, this classic shoe can be dressed up or down for years to come. And the toe? Anything but square. Get your pair here.



Mistake #5: Five Fingers Shoes

Despite a plethora of lawsuits, these shoes are still popular amongst barefoot running enthusiasts. Additionally, despite what these people may think, no one wants to see them wearing these monstrosities in public.


Italian shoe solution: The High-Top Sneaker

If you want to look sporty in the city, don’t wear shoes that are actually for participating in athletic activities. Our expertly crafted leather high-top sneakers are comfortable option to wear that won’t make onlookers ask “what the hell?” Get your pair here.