Style

The Fall Sneaker Upgrade

How to Elevate Your Autumn Wardrobe with a Few Pairs of Sneakers

By Diggy Moreland ·
2947b6c751dd3ccd1ad69a64767f059e
Photo: Timur Emek/Getty Images

Diggy Moreland made a name for himself on season 13 of The Bachelorette with his keen fashion sense and proclivity for bowties. He's also somewhat of a sneaker aficionado, with 652 pairs to his name. So you might want to consider his advice...

Too many men think that to have a great fall shoe game, they have to go with an oxford, wingtip, boot or loafer. But it’s 2017. And if you’re a sneaker lover like me, you can find a pair that’s more-than-appropriate for just about every sartorial situation imaginable.

Below, I’ve assembled four outfits for four representatively autumn-y occasions, from a Saturday with the boys to your best friend’s fall wedding. Then, I’ve upgraded those outfits with a specific pair of sneakers. That’s why this is called “The Fall Sneaker Upgrade.” But you knew that…

KITH

The Situation: You’re going to watch your alma mater take on your friend’s alma mater at a neutrally located sports bar. It’s Saturday. For the boys, etc.
The Outfit: Nothing fancy. Your favorite college crew, statement hoodie, great washed jeans and a pair of classic Adidas Superstars.
The Sneaker Upgrade: Try the classic New Balance 574 Sport in a hot new fall color: wheat. Your boys will not be expecting wheat.

The Situation: The first first date with that girl you met on Bumble at work at the bar of your choosing. Think: not fancy, not casual and just the right amount of hip.
The Outfit: A tailored button-down, slim-cut jeans and the typical leather boots (chuckha, chelsea, the like).
The Sneaker Upgrade: The Converse Hi-NBA Legend. It’s like a boot in unexpected sneaker form.  

The Situation: The after-work happy hour. Your boss is there. But he's taking shots, so...
The Outfit: A modern-cut blazer and a patterned button-down tucked into a pair of trousers that look like they cost make you feel like a million bucks. Plus, wingtip oxfords. Can’t forget those.
The Sneaker Upgrade: Replace the wingtips you and everyone else owns with a pair of Cole Haan Zerogrand Wingtips.

The Situation: It’s a college friend’s fall wedding. And you’re going stag.
The Outfit: A suit in a standout fall color (burgundy, forest green, etc). P.S. Don’t forget the bowtie, to show this isn’t your first rodeo.
The Sneaker Upgrade: Take a chance with these Veneto Lows in a classic black-and-white silhouette disguised as a sneaker. People will be wondering how you’re tearing up the dance floor in dress shoe—until they’re not.

Diggy Moreland made a name for himself on season 13 of The Bachelorette with his keen fashion sense and proclivity for bowties. He also owns 652 pairs of sneakers. And counting.

Elsewhere on the Daddy

More Style