The Best Men’s Shoes to Wear with Joggers

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Modern men who value comfort and style in equal measure can be forgiven if they need a little help figuring out what shoes to wear with jogger pants. 

Many of us recently spent way too long locked up at home in our favorite pair of joggers, and while there are a lot of things from lockdown we’re ready to discard (see you in hell, Zoom calls), comfy pants ain’t one of them. 

Man in black joggers jumping
Nowadays a good pair of black joggers is essential to a man’s wardrobe, but figuring out which shoes to wear with them isn’t always easy
[image: Emre Karataş / Unsplash]

Today the same stretchy and sporty joggers that previously gave you a cool WFH look can be paired with a denim jacket and button-down shirt to create a casual outfit that’s totally acceptable – and even essential – for everyday wear. 

The only problem? 

At home you could easily pair your joggers with warm socks or a cozy pair of slippers, but neither one is a particularly great option out in the real world. 

So without further ado, we’ve put together a list of the best shoes to wear with joggers to help you find the perfect shoes to take your athleisure game to the next level.

What Shoes to Wear with Joggers

Breaking Down the Best Types of Shoes to Wear with Joggers & Sweatpants

White Sneakers / Tennis Shoes

Man wearing joggers and white sneakers
[image: Public Rec All Day Everyday Joggers]

Quite possibly the most versatile piece of clothing a man can own, a crisp pair of white sneakers works well with pretty much every color and type of athletic pants: 

From black joggers made of French terry cloth to the kind of chino joggers that can almost pass for khaki pants

Bright colors like white tend to really pop against really dark colors like black and navy. 

But a lot of guys who wear joggers regularly don’t realize that white works just as well against neutral colors like beige and grey, especially in the warmer months. 

That versatility gives white sneakers a timeless style that makes them your best bet for joggers, and an excellent option for other casual wear like a pair of jeans, chinos or shorts

Sharp Selections: 

Trainers / High-Top Sneakers

Man wearing joggers and high tops
[image: Kushagra Kevat / Unsplash]

Trainers are decidedly sportier than low-top white sneakers, and therefore also more casual. 

The best way to pair them with your favorite joggers is to fully commit to the athletic look and pair them with another athletic piece up top, like a fitted white tee and a track jacket or a hoodie. 

Sharp Selections:

Dress Sneakers

Man wearing joggers and dress sneakers
[image: Hush Puppies]

Dress sneakers are one of the best options to pair with joggers because they combine the sharp toe shape and construction of a dress shoe with the sporty look of a more casual shoe, like a pair of chunky sneakers. 

Hybrid dress shoes (like the kind we recommend below) are often made from either genuine or faux leather. 

But dress sneakers are made from the same lightweight knit materials you usually find in a pair of sneakers, which gives them a more casual look. 

The result is a sporty shoe that works well with casual joggers or athletic pants, but still has a little more sophistication than high tops or slip-on sneakers. 

Sharp Selections: 

Hybrid Dress Shoes

Man wearing joggers and hybrid dress shoes
[image: Wolf & Shepherd]

Quite possibly my favorite shoes right now, hybrid dress shoes have taken the men’s fashion world by storm in recent years. 

They’re a great way to give your sweats a dressy look that’s a little more sophisticated because, as mentioned above, they pair a leather dress shoe upper with the comfortable sole of a sneaker. 

The result is a great shoe that gives your joggers a sharp, sleek look but is still very much in keeping with their more casual vibe. 

Handsome Hack:

The best joggers to wear with hybrid dress shoes are the kind that have a tapered leg, which can sometimes even look like dress pants at first glance. 

That combination of hybrids and tapered joggers may not be fancy enough to wear to formal occasions, but it will definitely help you look sharp and stand out in casual settings. 

Sharp Selections: 

Hybrid Ankle Boots

Man wearing joggers and hybrid ankle boots

One of the easiest ways to adapt the hybrid-and-joggers look for the cold weather months is to switch from hybrid dress shoes to hybrid ankle boots. 

Come fall, one of my favorite jogger outfits is to pair a bomber jacket and plain white t-shirt with a pair of (tapered, of course) khaki joggers and hybrid chukka boots.  

The result is a versatile getup that satisfies the casual dress code in most social situations, but feels a lot more comfortable.   

Sharp Selections:

Chelsea Boots

chelsea boots
[image: Noah Smith / Unsplash]

If you don’t want to lean into the inherently athletic nature of joggers, one of the best ways to dress them up a bit is to pair them with some proper (read: non-sporty) boot styles

Chelseas have an elastic side panel in lieu of laces, which make them easy to slip on and off.

They’re one of my favorite ways to dress up joggers because, much like athleisure gear, they’re easy, comfortable and versatile. 

On rainy days one of my favorite moves is to throw on a pair of sweat-wicking joggers with a dress shirt, a trench coat and a pair Chelseas, creating a look that’s sharp enough to go anywhere but weather-proof enough to stand up to the weather. 

Sharp Selections: 

Combat Boots

Man wearing black combat boots
[image: Logan Weaver / Unsplash]

Of all the different ways to dress up joggers, few are as masculine as pairing them with a well made pair of chunky black boots.

The great thing about wearing black (or, depending on the color of your joggers, brown) combat boots with joggers is that they immediately lend your look a rugged, more bad-ass vibe. 

(…which is otherwise pretty hard to achieve when you’re wearing what are essentially pajama bottoms) 

Sharp Selections:

The (Potentially Controversial) Recommendation: 

Do NOT Wear Slides or Flip Flops with Joggers

Man wearing joggers and slides
[image: Élison Bartolomeu / Unsplash
illustration: Irreverent Gent]

As I mentioned above, I firmly believe that joggers have their place in the more comfortable, casual world we now live in. 

And the shoe recommendations above should give you a smattering of fashionable jogger-outfit ideas that, while casual, can still look pretty sharp.  

But I cannot in good conscience recommend wearing rubber flip flops and sweatpants out in public. 

Flip flops are fine for the beach or the pool, and I even recommend them in my style guide about the best shoes to wear with shorts

But if you’re not wearing shorts, you shouldn’t be wearing flip flops. Period. 

If you want something easy and casual to wear with your joggers, try a good pair of slip-on loafers. 

You can get a pair of leather driving shoes for a slightly dressier look, or lightweight versions with a rubber sole that are as comfortable as sneakers. 

Both looks are significantly more stylish than flip flops, but just as easy to put on. 

Which means there’s absolutely NO excuse for being that guy who wears a tank top, sweatpants and flip flops on airplanes. 

Please don’t be that guy.  

Sharper (& Smarter) Selections: 

You Know What Shoes to Wear with Joggers

Now Find the Best Joggers to Wear with… Well, Everything
Man wearing joggers and white sneakers

Here at Irreverent Gent we like to say that shoes are the secret weapon of style.

And if you’ve read this far – thanks for hanging in there, by the way – you’ll now have a pretty good idea of how to choose the sharpest shoes to pair with your sweats and joggers.

But it’s a good thing you’ve kept reading, because if you really want to look your best from head to toe, you need to make sure you’ve got the right joggers for the job.

We’ve put together a comprehensive list of more than two dozen of the best men’s joggers, sweatpants and athletic pants which, like the shoes above, combine comfort, performance and (of course) style.

Check it out to find a good pair of pants that will help elevate your athleisure game even further.

Find the Best Joggers ➤

(Even) More (Awesome) Resources↓
More Advice on Men’s Boots and Shoes from Irreverent Gent:

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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