How to wear joggers in winter with layers

How to Wear Joggers In Winter: 3 Options

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Joggers. An item of clothing that has been so popular over these last few years. I confess that I wasn’t a huge fan when they first came out. But one way to be modern in our style is to try the newer styles and find what works for you.

Therefore, I ended up taking the leap a couple of years ago by getting a pair of joggers. And since then I figured it would be smart to learn how to wear joggers in winter.

Quote of the day: “Change is the law of life. And those who look only to the past or the present are certain to miss the future.” John F. Kennedy

One of my superpowers is figuring out how we can wear our clothing in many ways and for more than one season. So I had my stepmom and mother help out with different ways how to wear joggers in winter including our coats.

Just like any piece of clothing, not every item is created equally. The joggers we are showcasing lend themselves to be styled for winter because of their material. But heck, it all depends on what your definition of winter is as well as how much warmth you need.

How to wear joggers in winter
1-What are joggers?
2-Teddy coat, sweater, turtleneck, and ankle boots
3-Fuzzy coat, sweater, blouse, and loafers
4-Leather jacket, sweatshirt, scarf, and mules

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What are Joggers?

There are many different pants that could be considered joggers. Some people refer to sweatpants as joggers but some people get upset when you loop them together.

In my opinion, the difference between sweatpants and joggers is the silhouette. Most of the time, joggers have elastic or trim at the ankle that pulls the material in to create a slimmer silhouette. Whereas sweatpants can be wider at the legs.

When I was growing up, sweatpants had an elastic waistband and were sweatsuit material. Joggers can have these details also. Yet I see many of the joggers having a drawstring waist.

Insider tip: If you don’t like the drawstring, just pull or cut it out. If the waistband is elastic, you don’t need it.

Joggers came around when athleisurewear decided to be the biggest trend of the century. And for all intents and purposes, they started out as pants for working out. Yet, just like anything else, they have evolved, and you can see them worn for everything.
Of course, part of that fact is they are made in all kinds of materials like my velvet ones below.

Right now, I think any super casual pants can be marketed as joggers. For our examples, we all wore ones with slimmer legs that ends with some kind of ribbing or elastic.

Related post: Wearing joggers 5 different ways

How to Wear Joggers in Winter with a Sweater & Ankle Boots

Nancy is showing a muted color option for how to wear joggers in winter.

Nancy has this pair of olive green joggers. You can see that her pair has elastic at the ankle, but only at the back of the ankle. That’s what I mean when I say they aren’t all created equal. This gives off a straight-leg look instead of being more fitted.

Footwear can make a big difference in how to wear joggers in winter. Nancy chose a pair of low-rise ankle boots. These worked great, especially because her joggers aren’t as tight around the ankle.

A white sweater is an easy combination with the olive green and then Nancy also wore a sage green mock turtleneck under the sweater for warmth.

Insider tip: Do you like mock turtlenecks but have trouble finding them? You can always tuck your turtlenecks down twice on the inside for a clean look.


Even with a cabled sweater, a long necklace can give the outfit extra pizzazz. Nancy picked a brown necklace that goes with the overall muted vibe and carried that along with her earrings.

The purse also matches the olive green/brown color scheme.

Insider tip: Olive green and brown can look very similar in certain lighting. Don’t worry if they don’t match perfectly.

Fuzzy Coat with Bright Sweater

Charlotte focused on a bright colored sweater with her embroidered joggers

My mom opted to also wear a sweater with her joggers for winter, yet it’s a very different outfit from Nancy’s.
1-She wore a blouse under the crew neck sweater.
2-Charlotte incorporated all kinds of colors with the sweater, the hat, and even her accessories
3-Loafers were the shoe of choice. Since they are leopard print, they add a bit of print mixing to the look also.

Both Charlotte and Nancy thought that a teddy coat would be perfect for how to wear joggers in winter. For the winter months, your overcoat is really part of your outfit and there’s no reason not to have a fun one.

Related post: Ways to wear a teddy coat

What you don’t see until the back photos is the embroidery on one leg of Charlotte’s joggers. The colors in the embroidery were the inspiration for the rest of the look.

I love how the yellow really pops against the black joggers and is a fun contrast with the lighter pink.

Insider tip: Many stylists will tell you to pair similar brightnesses in colors, but playing around with all different hues and shades is what makes color combinations fun and interesting.


My mom and I did not coordinate to both wear berets. Sometimes these things just happen. I’m sure it doesn’t hurt that we have much of the same DNA. And we knew we would be outside this day. She coordinated her beret to go with the earrings and coat so it looks cohesive.

The red purse is a pop of color that really gives the outfit a modern edge. And since we would be walking a lot today, my mom chose her Walking Cradles loafers. These are the “Wren” loafers that are available in 5 other colors on their site.

Insider tip: If you are looking for comfortable shoes, Walking Cradles are my gold standard for comfort and style, and not only because I’m an ambassador for the brand. It’s actually the reason I’m an ambassador because they make my feet happy. Use code Jodie15 for 15% off your first purchase.

Velvet Joggers with Leather Jacket

I chose a heavier pair of joggers for the idea of how to wear joggers in winter and then added a leather jacket.

I think the velvet joggers are the perfect example of how you can take an athleisurewear item and make it into something that works for any day. The material makes them more upscale yet the comfort and silhouette are still the same as your workout joggers.

I found these joggers at a secondhand store. The brand is one of the fast fashion companies, but I tend to buy things because I like them. Not because of the brand per se. I figure that if I keep these joggers as long as I keep most things and wear them at least twice a year, I’m still helping the slow fashion concept.

And even though I don’t wear black much anymore, I just had to buy this thrifted leather jacket. I think it really struck my fancy because of the gold details and the longer hem in the back (see the rear photos below). The back hem is also almost a peplum, and I really just adore the silhouette.

It’s hard to see in these photos, but this sweatshirt has these plastic pieces on it, so it shines and sparkles more than just a knit sweatshirt would. I’ve had it for years, and I love how it’s a little extra!


Whenever I wear a solid top, I really like some kind of necklace or scarf to break up the expanse of nothingness. That’s why I grabbed this scarf, that my stepmom, Nancy, brought me back from Belgium.

I decided to wear my fur-lined mules and you might be surprised that I always wear Sheec socks with them. The mule Sheec socks keep my feet from getting sweaty.
The shoes are Walking Cradles “Walker” (which also come in black but are low in stock now since I’ve had them for years) have a fleece lining and so are the best way to wear a mule in the winter.

I liked the print purse to break up the solid pieces, and the beret brings in a pop of color (which I pulled into the outfit with my glasses and ring).

How to wear joggers in winter for different ages of women
How to wear joggers in winter for grown women

Photo credit: Rob Filogomo

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