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Dressing Up Joggers 101

by Alex John |

Even as we slowly emerge from the pandemic, one thing remains sure - athleisure is not going anywhere. As the workforce has slowly made clear, working from home is going to be a part of professional life for a long time to come. Because of this, the jogger, a stylized sweatpant style that has been implanting itself in the male wardrobe for years, is more important than ever.

Let’s look at three occasions, and three proposed outfits, where you can make the jogger work for you. It’s a balance between comfort, ease and elegance. And it is easier to pull off than you think. But first, let’s go over some guidelines about how to ensure you are putting out the message you want to be sending.


Always have your joggers, and other pieces, in good shape

Just because you are technically wearing sweatpants does not mean that you should look like you are in the gym training for a 10k, or on the couch for a movie marathon. Sweat stains, rips, fraying or tattered edges are all a sure way to derail your efforts to look good in joggers. And this goes for pairs that are purposefully “distressed” as well.

 Always be neatly groomed

The same goes for your hair, face and body when it comes to pulling off this style. For the joggers to casually set off your otherwise elegant appearance, you have to be looking your best to begin with. This means you will want to have your beard, stubble or mustache looking even and healthy. It also means that whatever you are doing with your hair, that you are doing it right. This is not a look for a just woke up-style of hair. Have your nails trimmed or manicured and keep your hands moisturized.

Always find a pair that fits right

With joggers, you have the fitted ankles to think about when it comes to sizing. You want to make sure the length is right and hits your hips and knees correctly. You want the ankle to fit closely and not blouse over or get tucked in your shoes. They should fit closely but not skin-tight. You do not want a baggy look or a “skinny jean” look.

Styling Joggers

Casual Meeting

Showcasing your joggers with the addition of a neat collared shirt, a dark blazer and a pair of loafers with no socks is a sexy, breezy way to present yourself. This kind of look is good for a team’s meeting with people you already know, the kind of event where jeans would be acceptable.


Pairing joggers with a leather jacket or bomber jacket can be a fun and bold way to be comfortable while still being festive. A pair of streetwear sneakers in interesting colors or patterns will round off the look.


Top off your joggers with a short-sleeve button down shirt or a henley. This is a good fall or spring look, as you can cover up as much as needed. The joggers provide you with a relaxed and fun vibe while still looking pulled together. A long-sleeve button down would be too formal to mix, but do make sure your shirt-sleeve shirt is crisp and ironed.