How To Style Your Basic Leggings For Fall

We all have a pair (or ten) of our most beloved black leggings stashed in our dresser drawers. With the autumn equinox officially here, the time is nigh to pull them out for regular wear. "Leggings are tricky to pull off if you want to avoid the 'always-up-for-an-ab-sesh' kind of look," influencer Camille Charrière told Vogue. Some can interpret the comfy standbys disparagingly, but there are countless ways to challenge that by styling them up or down.

The best part about leggings? They're incredibly versatile while being ridiculously comfortable — unless you stumble upon the tight waistband variety, which is antithetical to the entire concept of leggings. The perfect pair of leggings to interchange among outfits should be comfortable, opaque, and figure-hugging — there's nothing worse than leggings that sag at the ankles or slide down while you're out in public. Without further ado, here are five ways to make buttery-soft leggings part of your favorite looks as we approach fall.

Whether you were around to participate in the internet it-girl culture of the mid-to-late 2010s or not, no one can deny that some seriously cute 'fits spawned from sites like Tumblr and lookbook.nu. Even Vogue reported signs of the "2014 Tumblr girl style" resurfacing as early as January of this year. Still, with micro-trends evolving faster than the speed of light, this look is worth revisiting regardless of its current status. The fashions of the 10s fused elements of indie, goth, and scene trends to develop a covetable style that was all its own. An added benefit is that the rather dark aesthetic perfectly complements the ambiance of fall's colder months.

A notable ensemble of the times consisted of shorts paired with tights, which you can easily switch out for a cozier pair of leggings. Levi's 501 Original High Rise Black Cut-Off Denim Shorts from Lulus are perfect if you're lacking in the jorts department. Pair this outfit with era-appropriate accessories like a long cardigan sweater, tall boots, and a furry vest or leather jacket. If you really want to pay homage to the 2010s, break out your Jeffrey Campbell studded platform shoes to elevate things. All that's left is to put on some of the greatest hits by The 1975 as you cultivate hearts from your followers. Just don't forget that statement necklace and oversized purse on your way out.

It's easily recognizable by its fundamental components: leggings and sheepskin boots. Yes, the standard fall uniform is more than a little basic, if the memes that drag it each year are any indication. But there's something sentimental about this perennial fit, popularized in the early 2000s alongside the rise of the pumpkin spice latte.

If you haven't treated your toes to a warm pair of Uggs or Fauxggs (that's your garden-variety fake Uggs, for the uninitiated), you're truly missing out. Even the dourest critics of this style have to admit that it's tempting to throw on cozy fur-lined boots when the days are short and nights are long. While this outfit emphasizes comfort over sophistication, it's still worth trying, even if just to prove you don't care what others think. "It's a defiance in the face of the unrelenting grind of needing to be successful," style and culture writer Dave Schilling said about Uggs' power (via The Los Angeles Times).

If you don't have an old pair of Uggs lying around, you can purchase the iconic Classic Short II boot directly from Ugg.com for $170. For a similar style on a budget, try Bearpaw's Emma Short Suede Boot, starting at $28.79 from Zulily, where reviewer christy1960 claims "[they] are just as good, if not better than Uggs." Bonus points if you can convince your bestie to join you for an impromptu photo shoot at the local pumpkin patch.

Picture this: you wake up late, are strapped for time, and would love to look polished but need something fuss-free and warm on a chilly morning. To distract from the fact that you're even wearing leggings, you can sport your best mini or midi-dress paired with ankle or knee-length boots. "Focusing on staples that lend themselves to endless styling is essential for these moments in between seasons," designer Jenni Kayne explained to Harper's Bazaar. That said, you should probably leave summer's dayglo tropical print dresses in seasonal storage if you want to embrace the fall spirit fully. Still, we won't knock your eccentricity if you choose otherwise.

Pairing dresses with flats or heels might be tempting, but drawing attention to the hem of leggings results in an underwhelming effect, making the legs look disproportionately short. A perfect boot to suit nearly any style of dress is the clean-cut Sydney from Kork-Ease. Don't underestimate the power of color coordination; for instance, brown leggings can seriously elevate a dress paired with tan or brick-colored boots.

This look is sure to capture compliments with a bold piece of jewelry like chandelier earrings, in a nod to society girl and Warhol muse Edie Sedgwick. For accessories like hers, look no further than these Gold-Tone Chain Fringe Chandelier Earrings from Macy's. Try a simple chignon updo to highlight earrings if your hair isn't quite as short as Edie's famous pixie.

Many of us are familiar with the "leggings aren't pants" discourse that's existed for eons. Back in 2009, Glamour highlighted the argument, interviewing an anonymous activist who coined an actual movement against the legwear: "We're not in this for personal gain but for the good of mankind," they told the magazine.

While tapered leggings haven't quite secured their spot as substantial enough to be trousers, flared leggings are another matter entirely. Although straight-cut leggings have dominated the market in recent years, flared leggings seem to be gaining notoriety amongst fashion fans in everything from activewear to daytime looks. "Flare is the style right now, and TikTok is having a moment with it," fashion apparel analyst Maria Rugolo predicted in late 2021 (via CNN).

One pair of flares that can handle their own are Aerie's Real Me High Waisted Ruched Flare Leggings. Their ruched detailing and tailored fit have many Aerie reviewers referring to them as the "best leggings ever." Since the cut of flared leggings makes them more forgiving of footwear choice than their tapered predecessors, you can style them with everything from platforms to this season's trending ballet flats (via The Guardian). For those in colder climates, it's best to incorporate the flared legging into your outfits before you start trudging through the snow in the coming winter months. As anyone who's been tragically affected by frayed, soggy hems can tell you, they don't mix well with inclement weather.

Those whose formative years were spent roaming Hot Topic or watching "Pop-Up Video" will quickly recognize this silhouette. It shares elements of late seventies and eighties fashions and even had a brief renaissance in the aughts. Many millennials and Gen-X'ers still haven't let it release us from its grip, and it's won over everyone from pop stars to alt-girls.

A graphic tee, miniskirt, and leggings make up the foundation of this look, and you can drape them with a belt for true new wave sensibility. Although Harper's Bazaar referred to Madonna's "mini skirt layered on top of leggings" as elements of the worst in fashion trends, the composition can easily be redeemed.

To refine the style for a more mature incarnation, go monochromatic and play with textures. A slinky jacket over a worn-in graphic tee will elevate the outfit from costumey to chic; try a sheer zip-up top like Anatomie's Bailey Mesh Jacket if wearing black from head to toe. For added warmth, you might want to swap the graphic tee for an oversized sweatshirt or layer up with one. The best type of skirt to wear comfortably over leggings is something lightweight and flexible, like H&M's aptly named Mini Skirt. When it's time to finish the look, you can slip on a pair of tall boots or, in true eighties fashion, incorporate leg warmers and flats. And don't worry; you won't land on any worst-dressed lists.