In Your Comfort Era: The Guy’s Guide to Casual Slip-on Shoes Outfits

In partnership with Huckberry

If you’re like most guys, you’re not lacking in the shoe department. You’ve got sneakers. Your go-to work shoes. And you know exactly where to look in the back of your closet for those formal slippers you bust out for weddings. So you’re good to go, right? 

Not so fast.

While shoes are the easiest thing to shop for—after all, your size never wavers, and you don’t have to take your pants off to try them on in the store (I hope?)—I’m here to tell you that your footwear repertoire may still be missing a key category.

Shoes that can help you tackle those pesky, in-between outings—like a casual coffee date, or running errands in a busy place where you might just lock eyes with the one—in style. 

Enter: men’s slip-on casual shoes.

These easy, breezy styles look better than your house slippers but feel just as good on your feet. They’re perfect for when you’re trying to get out of the house as fast as possible and can’t be bothered with laces.

But what to wear with loafers, clogs, mocs, and more? I’ve got you.

The trickiest part of getting a slip-on shoe outfit right is to pair it with the right pants. So, read on for the style intel you need, and revisit this guide whenever you’re about to slip (pun intended) into a pair.

Below, discover 4 men’s casual slip-on shoes outfits to wear right now:

The loafer is the most put-together of the slip-ons. A shoe that commands respect without being annoying about it.

The style naturally pairs well with the most classic, smart-casual pants: a slim or slim-straight chino.

Want to give these shoes a more laid-back vibe? Reach for a pair of jeans in the same silhouette for your casual slip-on shoes outfits.

From there, build the rest of your outfit with a sweater or cardigan that keeps you warm while looking cool.

The most casual, and likely the lowest to the ground, slippers require the shortest hem for pants.

Ready to transition into fall looks? Tapered jeans or cropped trousers can do the trick without causing any pooling or having the back of your pants getting stuck under your heel—embarrassing!

Of course, if the weather’s warm, you can also wear your loafers with shorts. They’re the ideal summer sandal replacement when your feet aren’t ready for public viewing.

A moc is a great investment for fall when building out a repertoire of men’s casual slip-on shoes outfits.

Really! If I had to pick a slip-on that was the most versatile, the moc would get my vote.

They look right at home on a boat or a camping trip, but you can also take a cue from super-slacker Peter Gibbons in Office Space (which I recently rewatched at my local movie theater and totally holds up!) and effortlessly pull them off in your Casual Friday work looks.

Since it’s a sturdier shoe with a wider profile, pair your mocs with straight-leg pants to keep a streamlined silhouette, mmkay? That would be grrreat. 

Lean into the slack-lining, GORP-core vibe and pair your clogs with some relaxed-fit pants, like cargo pants or carpenter pants.

The 90s are back, and the workwear trend isn’t going anywhere, which means if you haven’t given into the Birkenstock Boston clogs trend yet, this is your sign to get onboard.

More men’s outfit combination ideas from SG HQ:

---

How to Wear a Vest and Not Look Like Mr. Schue from Glee

Which Jeans to Wear with Which Sneakers

20 Fall Jackets to Shop Now

Autumn Outfits Inspired by Starbucks’ Pumpkin Spice Latte