Winter & Fall Leggings Outfits: How to Style Them All Season

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This post will show you five leggings outfit ideas, with tips on how to look cute and stay warm while wearing leggings in the fall and winter.

I’m not ashamed to admit it: I love leggings, and I wear them as pants all the time. There’s nothing quite as easy as throwing on a pair of basic black leggings and calling it a day!

In this post, you’ll find stylish leggings outfit ideas for the fall and winter, along with tips for staying warm while wearing leggings, plus the best kinds of shoes to wear with leggings.

Tips for Staying Warm When Wearing Leggings

In the fall and winter, leggings are a staple, but I think most of us have experienced regret at some point for wearing them out in the cold. Whether your leggings were too thin or a gust of cold wind whipped at your ankles (I’m looking at you, 7/8 leggings), leggings aren’t necessarily the best choice — but they can be if you follow these tips for staying warm:

  • Opt for thicker fabrics. Certain leggings, especially cotton ones, are too thin for chilly weather. Instead, choose leggings that are thicker, or better yet, lined with a warm lining like fleece that will help you retain heat.
  • Wear longer tops and/or jackets with your leggings. By opting for tops, sweaters, jackets, and coats that are longer in length (that cover your backside), you will stay warmer… and also avoid the hotly debated issue of whether leggings are considered pants or not.
  • Don’t leave your ankles exposed! Most leggings are ankle-length, and depending on your footwear, your ankles might be left exposed. And while that is perfectly fine during other seasons, in the fall and winter, it’s a recipe for feeling cold. To avoid this, go for shoes that rise above your ankles, like boots, or if you’re wearing sneakers, opt for high socks that will keep your ankles covered (and warm).

Luckily, leggings look great with almost any kind of footwear — emphasis on the “almost.” The very best footwear options for wearing with leggings are sneakers and boots of various heights (ankle, mid-calf, knee-high, and over-the-knee boots all work).

Since leggings have an athletic look to begin with, sneakers are always a prime choice. You can go full-on sporty with your outfit or go for a more relaxed athleisure look, depending on your vibe.

Boots are a must in the fall and winter and do a good job of balancing out slim-fitting leggings with their bulkier build. The choices are endless: combat boots, rain boots, Chelsea boots, you name it! They all look pair perfectly with leggings.

Unless you’re keeping it ultra-casual with some slip-on footbed sandals, I’d avoid wearing leggings and sandals, as these tend to look a bit mismatched. Sandals are better suited for summery items like shorts, skirts, and dresses. Flats are not an optimal choice for leggings either, as the proportions will look a bit off when worn together; instead, go for clogs and certain slippers (like platform Uggs).

Leggings Outfits

Now, let’s get to the good part: the outfits! Check out these leggings outfit ideas for styling inspiration in the fall and winter.

Class to Night Out Leggings Outfit

So you have plans after your last class of the day, and you don’t have time to go back to your dorm (or college apartment) to change. *And* you want to be comfortable by wearing leggings. I’ve got you covered!

Your best bet is a pair of black flared leggings with a high-rise: these will look best with going-out tops rather than basic slim-fitting leggings. A small flare or bootcut will help to balance out the proportions of your outfit, plus they look cute worn with some black ankle booties with a short heel. This Chelsea-inspired pair has chunky lug soles with a short heel that is casual enough to wear during the daytime to class but also great for nighttime (or happy hour) wear.

The key to going from class to a night out during the fall is your outerwear. By wearing a class-appropriate jacket like an oversized plaid shacket over your going-out top — which can be a crop top, a corset top, a bralette, etc. — no one will be able to see what you’re wearing underneath! (So long as you keep it buttoned, of course). Then, once you get to your next destination, ditch the jacket and show off your cute top for the full effect. Layering is key for transitional outfits like this one.

You probably don’t want to bring your backpack to the party, bar, or wherever you’re headed, so opt for a tote bag instead. Be sure to accessorize with your favorite jewelry that will help your ensemble feel more dressed up; hoop earrings and a necklace can go a long way.

Faux Leather Leggings Going Out Outfit

Now if you’re headed on a night out and don’t have to worry about any classes right beforehand, you can go all out and rock a pair of faux leather leggings. These are the ultimate way to dress cool yet be comfortable, thanks to their leather-looking exterior.

Wear them with an eye-catching crop top like this silver rhinestone crop top which is giving major NYE vibes, especially when paired with some sparkly silver drop earrings. An oversized black blazer is the perfect way to ground the look and drape over your shoulders throughout the night.

As for footwear, you can wear over-the-knee boots, ankle booties, or heels. These black pointy-toe pumps with silver embellished ankle straps and bow details would be a stylish choice, along with a trendy silver knotted handbag.

Athleisure Leggings Outfit

Of course, when it comes to athleisure and athletic outfits, leggings are the ultimate choice. For practical reasons, they are elite for workouts or athletic activities, but they’re also super comfy for just chilling in.

Either way, you can’t go wrong with some black athletic leggings (which are going to be thicker in fabric than cotton leggings) paired with running shoes and some crew socks.

A zippered fleece jacket (I love this one’s contrasting color scheme) is going to keep you warm in the fall and winter while also allowing you to move around comfortably.

By adding in cool accessories like some trendy sunglasses and a bright beanie hat for a pop of color, you will elevate this outfit and give it a “model-off-duty” look that makes it just as great for running errands or school as it is for going to a workout class.

Fall Leggings Outfit

My favorite way to style leggings during the fall is with long, structured coats and boots. This combination is effortless but looks so chic.

Throw on some black leggings — this ponte pair is going to wear more like pants thanks to their heavier fabric — and a pair of chunky ankle or mid-calf boots. Rain boots and combat boots look great with this pairing, as well.

A longline coat is going to make the ensemble look put-together and fashion-forward — bonus points for one with a plaid print that looks autumnal. Wear it over a neutral-colored oversized sweater or shirt, and accessorize with a pair of gold hoop earrings. It’s an easy, comfy, and stylish combo.

Winter Leggings Outfit

Winter time calls for your warmest clothing pieces, and while leggings may not instantly come to mind, a pair that is fleece-lined should do the trick. I highly suggest investing in a pair so that you’ll still be able to wear leggings even when it’s cold outside.

Bundle up in an oversized mock neck sweater (this one features an adorable fair isle pattern) and an ultra-warm puffer jacket. Not only is this neutral puffer stylish thanks to its flattering cinched waist detail, but it also boasts water-resistant and light-reflecting fabric. Plus, it’s long enough to cover your backside, making it legging-friendly, and it will keep you that much warmer.

Wear some warm socks over your leggings to retain heat, along with a pair of lace-up hiker boots or winter boots. I’m a fan of the faux shearling accents on these boots, which also feature durable lug soles. A matching knit beanie hat with a faux fur pom is going to add a cute touch while also being a must-have accessory during the chilly winter season.

What do you think of our winter and fall leggings outfits guide?

Would you wear these outfits? Which leggings outfit is your favorite? Leave a comment and let us know!

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