Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

How to Style Joggers

Let’s break down how to style joggers. 

Last month our series, “What to Buy at,” featured Banana Republic. I love BR for their classic modern style and commitment to offering an inclusive size range. They make my job so much easier. 

After that post, I received several questions about how to wear these joggers, specifically, how to style joggers in an outfit for work and weekends. So today, I’m breaking down a few options to wear for whatever work looks like for you and ideas to make them casual, since right now those worlds are merging together. 

If you are new to our site (welcome!), today is an excellent example of how many of our posts are designed to help you build a functional, practical, and chic wardrobe. I use items from popular, mainstream retailers, focusing on realistic price points and inclusive size options. 

My goal is to help you build a wardrobe much like I did when I worked with my private styling clients. I reuse popular items throughout each season, so what you purchase through this site becomes a piece you turn frequently. 

In the looks below, I used a combination of items you may already own, along with some new options, all well priced, all available in a range of sizes. 

How to Style Joggers for Work 


How to Style Joggers


Joggers, $56

Maybe the best thing to come out of 2020 is jogger pants. They are having a big moment. With work and home life being one and the same, it’s nice to have a few pieces you can grab that straddle both worlds.

The cut, tapered leg, and drape of a jogger make them a more polished alternative to leggings and sweatpants. At this point, we know how much better it feels to get dressed in some capacity for our day. Feeling pulled together makes all the difference in our mood and productivity. 

These BR joggers are best sellers, on sale for under $60 in a range of sizes and colors. Black (above) and olive (ideas below) are the easiest colors to wear. Sizes are inclusive up to a XXL in missy and petite. 

Like Black Pants


How to Wear Black Joggers Three Ways

Sweater, $41, Loafers, $140, Crossbody, $130

Don’t let the casual nature of these pants throw you. Wear them like you would any pair of black pants. Here, I used this black and white marled sweater from Gap. It’s easy-peasy, comes in regular, tall and petite up to an XXL and on sale for $41. This is suppose to be oversized, not giant, but not fitted. I like how the sweater complements the joggers; both feel cozy and casual.

Then, to add a level of polish, some better pieces, like a structured crossbody bag by Madewell and these insanely comfortable loafers by Birdie

With a Jacket

How to Wear Black Joggers Three Ways


Tank, $48, Jacket, $169, Heels, $105, Hoops, $60

The trick to wearing a casual jogger with a jacket is to make sure the fabric of the jacket works with the jogger’s material. Here,I’m using the Ann Taylor motto jacket we featured earlier this month. It’s done in a knit, which means it will complement the blend of the joggers.

As a layer,I used this popular sleeveless shell (also from BR, in white and black). For this look, tuck the shell into the pants and give it a little blouse by pulling it out a bit.

Then, I added block heels in a python print that combines the two neutrals.

Finally, because the motto’s zippers are silver, you want to wear silver-tone accessories, like these hoops. It will help the look feel purposeful.

Party Up Top



How to Wear Black Joggers Three Ways


Sweater, $47, Necklace, $48, Earrings, $195, Lipstick, $28, Slippers, $120

If you are working from home and Zooming all day long, keeping things polished up top and comfy below is sometimes the way to go. 

Here, I’m using another Reader Fave, this under $50 silk and cashmere-blend sweater (members of our Private Facebook Page RAVE about it). It comes in six seasonal colors; I’m featuring the “pine.” 

When video conferencing, think about wearing colors that bring light and warmth to your face. The sweater is a lovely base to add some simple accessories, like a chain link necklace and stud earrings. These small details will add layers to your look and help you look more professional. 

What’s not professional are these Ugg slippers 🙂 Who knew when I bought them in late 2019 just how much I would wear them, lol. 

Finally, consider your make-up if you are regularly on camera. You may need a darker or brighter lipstick, so you don’t look washed out. My favorite is this red lip by Kosas.


Below is our article from March (when all of this nonsense started).  I used a similar pair of olive joggers to create three casual outfits. Almost all of the items are still available. 

How to Style Joggers for the Weekend 

How to Style Joggers for the Weekend


Joggers in olive, similar here

Joggers are what you want to wear when you don’t want to wear sweats. They are slightly better, and make all the different in that space between feeling sloppy and like you still have your life together. 

I’m featuring them in a dark army green. It’s a fantastic, updated neutral. 

Let’s dive into the first outfit: 

White Tee and Denim Jacket

Three Ways to Wear JoggersJoggers,   |  Tee, $25  |  Jacket, $79  |  Sneakers, $50

You likely have these pieces already hanging in your closet. I want to call out the tee shirt because it’s what many of you are looking for.  It’s a lovely ballet neckline with a sleeve that goes to your elbow, making it ideal for layering or to wear alone.

It’s available in: white here,  from a 00 (XXS) – 18 (XXL) and plus size 1X – 4X here. 

Then I added our favorite denim jacket by KUT. I just love it, I wear it all the time. It’s available in petite and missy up to an XXL.

Finally, I included these sweet tie top sneakers by Vans. I almost stopped myself from featuring them here, since my girls are obsessed with their slip on version, but these, with their contrasting sole and warm “marshmallow” color feel right for grown ups

Cozy Sweater

Three Ways to Wear Joggers

Joggers,  |  Sweater, $25  |  Necklace, $40  |  Sneaker, $48 

Temperatures are all over the place right now, at least on the east coast. One day it’s warm, the next it’s dark and chilly. 

My love of H&M sweaters is well documented. So I paired the joggers with this white, slightly oversized turtleneck sweater. (It’s getting limited in sizes but is available in regular and petite.)

I added a long necklace by Kendra Scott (on sale for under $40 at Nordstrom Rack) – because why not? Jewelry makes me feel human. 

Finally, I am crazy about these shoes by Louise et Cie. They are a leather slip on sneaker in a leopard print available in lots of sizes for under $50, also a Nordstrom Rack. I was not allowing myself to buy another leopard print shoe, but will be breaking that rule with these. 

Better Than a Sweats


How to Wear JoggersJoggers, $69.50  |  Sweatshirt, $38  |  Flats, $145  |  Earrings, $36 

I took the joggers and added a simple grey sweatshirt by Everlane. I find they run slightly small, so size up, or pay close attention to the measurements. 

Then I added these chic and comfortable Rothy’s in camo. I’m wearing my Rothly’s in my office almost daily. There’s something about wearing a real shoe that helps me feel grounded.

Now, keep in mind, my office is a few steps away from my house. I have to go outside to get in, so wearing shoes is required. I get it might be less important if you are currently working at your dining room table – just something to consider. 

Finally, these earrings, by our new favorite Gorjana. I’m mentioning them because they come in gold AND silver tone, and so many readers have requested more silver options. They are incredibly affordable and a simple way to raise your spirit. 

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist View Post and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please consider following on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

How to Style Joggers

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

Never Miss a Post

Enter your email address below to sign up for our newsletter and get your free copy of our Wardrobe Essentials Checklist sent to your inbox.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Jennifer Carver

Sunday 13th of February 2022

For the turtle neck sweater look… do you leave it loose? Partially tuck it in? Wasn’t sure.

Megan Kristel

Tuesday 15th of February 2022

I like a tuck, but it's really up to you! :)

Gerin Canin

Wednesday 7th of October 2020

I like these pants. It's too bad the length is so short and BR doesn't offer them in tall.


Wednesday 7th of October 2020

This might be one of your most useful posts ever (for me, at least). Thank you for the breakdown and ideas!!😊


Wednesday 7th of October 2020

For the BR joggers, if you are in between sizes, would you size up or down? Do they have a little stretch? Wouldn’t want them baggie. Thanks

Marylyn Ritchie

Saturday 28th of March 2020

Thank you for this post. During this "stay-at-home" order in the Philly suburbs, I have been trying to figure out what to wear with my joggers. And I agree with you 1000% percent that getting ready for the day "pretending" that I have somewhere to go makes it a MUCH better day.

Thanks for continuing to post and encourage women through this crazy time. We will get through this together.


Tuesday 24th of March 2020

I agree with you about the positive comments, which we all crave and need now (and always). I wear a similar look to this and TOTALLY agree with you in that the look can work for many, it's just piecing the right things together to feel good I am just under a plus and LOVE this type of look and feel good in it. THANK YOU


Tuesday 24th of March 2020

Gathered at the waist paints do nothing for people with bellies, other than make them look fatter. If you are shorter in stature and heavier set, you need to avoid wearing dirndle skirts or anything with a gathered waist. So while this look is good for skinny people that are in shape with a slender silhouette, it doesn’t do much to enhance the shape of pudgy people.

Megan Kristel

Tuesday 24th of March 2020

Do we really need negative comments right now? Any size can wear any style, it's all in how that particular piece fits the individual and how you pair it with other pieces. I don't have a flat tummy and I wear this look all the time.


Tuesday 24th of March 2020

Great look! One question...with the t-shirt/jean jacket combo, what's the better look - leaving the t-shirt tucked in, partially tucked or untucked?

Megan Kristel

Tuesday 24th of March 2020

I'm a big fan of the partial tuck because it helps bring you in and minimizes our midsections. It seems counterintuitive but it's actually ag great slimming trick!