These Legging Styling Choices & Trends Are Firmly Outdated In 2026

Leggings have been a staple in our closets for decades, and for good reason. A good pair in black or another neutral color goes with anything and creates a flattering, slimming silhouette. Over the years, legging trends have taken over, and we've seen everything from statement patterns to '80s stirrup pants. And the way folks have styled them has evolved as well. According to personal stylist and image consultant Cynthia Kennedy, certain ways you wear leggings will have you looking completely dated in 2026.

Although there has been a shift from super tight pants to baggier fits, leggings aren't going anywhere. Much like a basic white tee or a button-down shirt, spandex tights are a part of our capsule wardrobe. However, Kennedy exclusively tells Glam, "A number of pairings have begun to look like they belong in the mid-to-late 2010s." So how do we look like we didn't just step off the "Gossip Girl" set? Our expert stylist shows us all the ways to avoid outdated leggings trends while staying current when it comes to our fave comfort pants.

During the early aughts and 2010s, tunics were worn with everything from flared jeans to slim-fitting trousers. The super versatile top was perfect for elongating torsos and minimizing the midsection, but they're no longer in fashion these days, especially when paired with black leggings. "For years, this was the go-to 'Pinterest mom' uniform, but the proportions come across as heavy and too predictable these days," Cynthia Kennedy exclusively tells us. The founder of Your Style Transformation Academy also advises against adding riding boots, as they'll further make your 'fit look like a thing of the past.

Kennedy shares, "Lately, fashion is trending toward a more polished and intentional approach, even in casual wear. Rather than making leggings the default for every occasion, they are being incorporated into outfits with more thought." Instead of long tunics, style your basic leggings for fall with cropped jackets or a chic sweater. Kennedy loves the Everyday Legging from Spanx if you want to elevate your look with a blazer or longer coat.

While working out, wearing leggings with a high sheen or gloss can make us feel like a modern-day superhero. However, stylist Cynthia Kennedy thinks they should only be reserved for the gym and not incorporated into your daily 'fits. "These shiny leggings can look too sporty when worn with regular clothing instead of workout wear," she exclusively shares with Glam. For a more elevated approach to leggings, turn to higher-quality fabrics in a matte finish, such as the Align High-Rise Pant from lululemon, Kennedy advises.

When shopping for leggings, look for thick, durable material that will last years. "A quality, well-fitting high-rise in a matte fabric will have a longer life than trendier versions or anything with flashy finishes and excessive details," Kennedy says. The style guru adds, "I remind clients that the 'best' legging isn't necessarily the trendiest. It's the one that flatters your proportions, works with the rest of your closet, and stays opaque when you move." We recommend doing a fit test by squatting, sitting, and bending over while trying on your leggings to see how they'll hold up in various situations. Anything even slightly see-through should stay on the rack.

There was a time when leggings were a statement piece, with many favoring colorful galaxy patterns, loud prints, and mesh fabrics. Although they may have been hip in the mid-2000s, we're going for a more quiet luxury approach in 2026. "You will not see as many busy printed leggings or dramatic cutouts in everyday style now. Cleaner, more elevated designs have taken their place," Cynthia Kennedy exclusively shares with Glam. According to her, you'll want to look for structured silhouettes with a more minimal finish.

If you want to up your leggings game, try a pair of stirrup pants with ballet flats or kitten heels. "They've made a comeback and give your outfit a tailored, fashion-forward feel," Kennedy notes. And for a looser look, flared yoga pants are totally trendy now. "These are nothing like the early 2000s versions. The lines are cleaner, and the fabric is thicker," she tells us. Our stylist recommends pairing them with a cropped sweater or fitted top for a modern look. Y2K-adjacent but updated? We're all for this aesthetic.

Once in a while, non-conventional silhouettes will trend and take over mainstream fashion. Enter the waterfall cardigan, with various celebs embracing the draped, buttonless style over leggings in the late 2000s, and then adding chunky jewelry to boot. Cynthia Kennedy tells us this is a firm "no" on her part in these modern times, so step away from this outdated look. "Leggings with waterfall cardigans and statement necklaces were very popular ten years ago, but the layering feels overly done and visually dated today," she exclusively shares with Glam.

Waterfall cardigans are admittedly great for covering derrières or creating volume at the bust because of the excess fabric, but replace them with an oversized button-down for a fresh take, Kennedy tells us. And the one shoe that will always dress up leggings is a good pair of loafers. "The juxtaposition of the two gives you a relaxed yet tailored look and still feels fresh and sophisticated," the fashion expert points out.

Any article of clothing with the words "low-rise" makes us recoil, especially when associated with leggings. Add a long, fitted top to the mix, and your OOTD is officially outdated. "Not only are they less flattering than higher-rise alternatives; the combination of long, clingy tops gives a silhouette that is no longer current," stylist Cynthia Kennedy exclusively tells Glam.

Our expert's rec is Athleta's Elation Ultra High Rise Legging, which comes in a variety of shades and lengths to fit all sizes. Kennedy also loves the High-Waist Airbrush Legging from Alo that features a silky matte finish that gives your bottom half extra support while sculpting it at the same time. What we particularly love about high-rise leggings is that we can pair them with a trendy crop top without baring too much skin. Anything that falls past the hips can look way too Y2K, especially if it's too tight. For a no-fail 'fit, Kennedy says, "An off-duty look with high-rise matte leggings, an oversized blazer, and some sleek sneakers is polished and put-together, yet really comfortable." Trends may come and go, but a good pair of sturdy, no-shine leggings will always serve.