Is it just me, or do you start boycotting pants during the winter too? When I’m cold, I just want to be cozy over everything else! See ya, skinny jeans! Bye, wide leg crops! I’m all about leggings outfits and jogger pants now. ?But the fashion-lover in me hates wearing the same thing over and over again. So, that’s where these six winter jogger pants outfits come in. Joggers might be one of the most versatile winter pant options. They can be casual, they can be dressy, but they’re always comfortable. And who doesn’t want that?! 

Six Winter Jogger Pants Outfits

Before we get into the outfits, let’s chat about the jogger pants. Because honestly, having the right pair really makes a difference in whether they can be dressy or just a sweatpant! I always prefer a slim, body-skimming cut. They don’t need to be tight, but they can’t be too baggy! The best pairs skim your leg and still have some structure.

Having the right fabric also makes a difference! Instead of a fleece, I would suggest a heavier cotton fabric or a softer drape-y fabric. Velvet is another option that gives off a dressier vibe! (I own these velvet ones myself! TTS!) 

My current favorite joggers are the Lou & Grey Sweatpants from Loft. Although Loft calls them sweatpants, they have a draped, slinky fit that looks much dressier! But they still have an elastic waistband and super-soft fleece fabric inside. I now own two pairs of these and recommend them to everyone! They fit relaxed, but I stuck with my true size medium!

Sweater and Jogger Pants Outfit

We’re starting off with a good mix of casual and dressy! By tucking in an oversized, cozy sweater, the jogger pants instantly have a slightly dressier vibe. The shoe really makes a difference too! You’ll see in many of these looks that a sneaker works! But by opting for a pointed flat, the outfit is instantly elevated! With the pop of red, I’m feeling a fun, festive vibe!

I would wear this look everyday for errands, but I could also see it working well for a casual holiday party look! You could even add a heel to dress it up even more! (You can scroll down to see me style these pants with heels later in the post!) 

Sweater (medium – TTS for relaxed fit) | Pants (medium – TTS) | Flats (size down 1/2) | Earrings 

Graphic Tee, Denim Jacket, and Jogger Pants Outfit

If you want to know my most-worn jogger pant outfit, this is it, y’all! It’s casual, comfy, yet still pulled together, and I am all about that! To pull this look off, you can use any tee in your wardrobe! A classic white works just as well as a graphic version. But I love the personality a fun graphic tee adds! You could even layer with a lighter turtleneck or crew neck sweater for a more classic look!

And you know what I’m going to say, right? Be sure to tuck that top, y’all!! Keeping it untucked not only looks sloppy, but it also hides the waistline! My tee is very oversized, but by tucking it, the entire outfit looks more tailored to my body! And the jacket does a great job of framing the figure and providing structure. 

Jacket (medium – TTS) | Tee (large – stay TTS) | Pants (medium – TTS) | Sneakers (I sized down 1/2)

Button Down, Cardigan and Jogger Pants Outfit

Tell me the truth: do these not look like dressier pants?! It is all about the items I paired them with! My white button down is one of my most-used items (especially in style sessions!), and it’s because adding it to an outfit instantly gives off a classic, elevated outfit look!

The other pieces are tailored, and classic too. Instead of wearing a super-oversized slouchy cardigan, this one is more body-skimming! For the shoe, again I went with a classic pointed-toe flat. To keep it dressy, you could also go with a heel! But for a more casual look, a white sneaker would dress the outfit down!

Cardigan (small – size down) | Button down (small – size down) | Pants (medium – TTS) | Flats (TTS) 

Sweat Set Outfit

I love a good sweat set! Who doesn’t want to walk around in a sweatshirt and sweatpants all day, right?! But there is something specifically more dressy about a solid set like this all-black look. Don’t get me wrong, it’s still one of the most casual options of all the jogger pants outfits. But the two pieces together give off a jumpsuit vibe that I’m definitely into! And what I love about a classic set is that it layers up nicely too!

Sweatshirt (small – size down) | Pants (medium – TTS) | Sneakers (I sized down 1/2) 

Here they are paired with two different jacket options! I love that the camel coat gives the set a more sophisticated look, while the denim jacket is the perfect casual, more trendy look.

Camel Coat (6 – Size down) | Denim Jacket (TTS)

Turtleneck, Utility Jacket and Jogger Pants Outfit 

I recently shared seven utility jacket outfits with y’all, and yup! This type of jacket works with jogger pants too! For this look, I went with a more slim-fitting turtleneck, but a more relaxed sweater would work here too! It would be just as cute with the heavier weight gray sweater I shared in my first look up top! Just with all the other looks, I recommend tucking in your sweater (or even just front-tucking!)! 

And maybe I’m becoming a broken record here, but the shoe makes all the difference! The flat I chose dresses the look up more! But you could always go with a more casual sneaker too!

Turtleneck (medium – TTS) | Jacket (small – size down) | Pants (medium – TTS) | Flats (I sized down 1/2) 

Blazer, Tee, and Jogger Pants Outfit 

If Blair Waldorf grew up and had kids, she would totally wear this outfit. ?It’s just further proof that a good structured jacket and dressier shoe can make all the difference! I would wear this with sneakers too! I actually most often pair my blazer with sneakers for a more casual look. But together, they definitely give off a dressier vibe. No one would ever look at this outfit and guess I’m just wearing comfy jogger pants! 

Blazer (small – size down) | Tee (medium – TTS) | Pants (medium – TTS) | Heels (TTS) | Headband set 

So overall, here are the top takeaways I hope y’all got from my six winter jogger pants outfits!

Tuck those tops, friends! It will prevent your looks from getting sloppy, and more importantly, it will highlight your waistline! Adding a structured jacket will instantly elevate any look! And lastly, pay attention to your shoe! For dressier looks, a pointed toe flat or heel will make a huge difference! 

See more style sessions here!