How to Wear Leather Joggers: A Wardrobe Stylists Guide

How To Wear Leather Joggers

Maybe this is a weird Christmas to New Years post, but honestly, I’ve been receiving quite a few questions about leather joggers recently. So I thought it was worth addressing… How to wear leather joggers? Are they worth it? Will they be in style for a while? (ha, that was a rhyme!) Can they be dressed up? And dressed down?

There are all kinds of leather and faux leather joggers out there - at various prices. Personally, I’m not a fan of the faux leather leggings, especially the Spanx brand, because in my humble opinion, they’re a big pain to get on and off. They’re like girdle pants (which is exactly how they’re marketed) but for me it’s a wrestling match every time I need to go to the loo - and that’s no fun.

Tips for Finding the Right Leather Jogger for You

Leather joggers, however, still give that elevated, casual, sporty but edgy feel, but with a more relaxed silhouette (and therefore easier bathroom breaks!). Here are a few tips to find the right pair for you:

  1. Joggers are supposed to be drapey, so look for a leather (or faux leather) that is less stiff and has some movement to highlight your shape.

  2. Find a pair that sits close to your natural waist. Because of the proportion of joggers you want to see the small of the waist in contrast to the volume at the hips and thighs. Basically, low rise joggers are not going to be as flattering.

  3. Look for joggers that either have a cuff that can be rolled up or down OR a zipper that can be zipped or unzipped. This will allow for maximum footwear versatility.

  4. READ THE REVIEWS! This sort of goes for anything you’re going to purchase, and in the case of leather or faux leather joggers it’s essential for knowing what size to pick. For instance, the Commando pair I love, stretches A TON, when worn. All of the reviews say so and IMHO it’s true - so size down if you can.

Let’s focus on the Commando faux leather joggers, because that’s the pair I decided to buy after trying on many pairs over the past few years. 

How to Style Leather Joggers:

Dress Them Up

Let's start with dressing the joggers up. It’s a great study in the Rule Of Juxtaposition. The casual joggers are dressed up with a sparkly top and heels. The footwear makes a big impact with this look. The feminine pointy toe pump tips the scale to make this a dressier look.

Outfit details: 

Sequined top - runs true to size, and not itchy the way some sequins can be. I’m wearing a small

Leather joggers - very comfortable. They run slightly large and definitely stretch - size down if possible. I’m wearing a small and should have gotten an XS.

Suede pumps - truly my most comfortable pump, run TTS. There is arch support and various widths available. Tons of colors too. IMHO, worth the investment!

Sequined clutch - Not a fancy bag but a definite outfit finisher. Under $100 and can hold a phone, glasses and more. Love how it punches up an outfit.


Dress Them Down

I love the idea of wearing a leather jogger as exactly that, a jogger. The fabrication makes the overall outfit feel a little more spice than sporty, which is fun. Great weekend look that feels “nicer” than a typical gym set.

Outfit Details

Sweatshirt: From an Evereve x Love Squad collab. It’s slightly cropped but without belly showing so it pairs perfectly with a jogger without having to tuck in. Runs tts - I’m wearing a small

Jacket: This one is soooo good. It looks completely different when zipped or unzipped. I’m wearing a size 2.

Sneakers: My new favorite brand, On Cloud. These are a little more fashion forward for the running shoe brand with the colors and the zig zag closure. They run tts - I’m wearing a 7.5.

Leather joggers - SAME comments as above - but with this shoe I folded the cuff in half to show a bit more ankle.


Dress Them for Work

I like that these joggers can be worn for so many various occasions. And they’re extremely comfortable too.

Depending on your work environment, pairing them with a silk top and a third piece topper (in this case a cardigan, but a blazer would work well too) takes the joggers to a business casual level. And, the boots also help elevate the look. If it was worn with sneakers it would make it less dressy.

Outfit Details: 

Top - An easy “silk” cami in an unexpected color. Strapless bra friendly.Runs TTS, I’m wearing a small.

Cardigan - I LOVE this piece. Soft and cozy and hits at just the right place on the waist. Runs TTS, I’m wearing a small

Leather Pants - SAME info as above. I much prefer the joggers being worn outside the boots and not cuffing them for this outfit.

Bag - My new fav bag that goes with almost everything. They’re made from vintage scarves so each one is unique.

Boots - Crazy comfortable, especially for a 90 in heel. I love them so much I order them in black suede too. They sent 2 sizes to try and I ended up with a 6.5 wide.

Necklaces - A gaggle of necklaces from Freida Rothstein and Perle by Lola.


Casual Plus

I’d call this look casual plus. It’s not quite business casual and also not super casual - meaning you could wear it to some workplaces if there was a no jeans or sneakers policy and look put together. In this case, the joggers were tucked into the combat boot to showcase the ankle.

Outfit Details:

Sweater - Cozy and soft. I ordered this too big. It’s a medium and very generous. It would look cute with skinny jeans or legging too.

Leather Joggers - SAME as above - this time I tucked the joggers into the booties.

Boots - super old combat boots - I linked similar.

Bag - My newest everyday bag. Lightweight and easy to carry.


Here’s a roundup of the leather joggers I’m wearing and others that caught my eye:

And please KEEP THE QUESTIONS COMING! Truly, my best posts come from your questions. TYSM!!!


How To Wear Leather Joggers
How To Wear Leather Joggers
How To Wear Leather Joggers
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