How to Style Winter 2025’s Biggest Skirt Trend, According to Three It Girls
Every winter brings its own signature silhouette, and for the 2025 season, the clear frontrunner is the midi-length pencil skirt. Sleek, structured, and surprisingly adaptable, the pencil skirt has stepped back into the spotlight—thanks largely to three It girls who were spotted styling the piece in completely different ways during the holiday week.
It’s a trend that mirrors the mood of the moment: a mix of practicality, power dressing, and a desire for outfits that look intentional even when we’re just running errands. With political frustration simmering, workplace conversations resurging, and fashion leaning harder into femininity-with-a-backbone, the pencil skirt feels right on time.
Whether worn polished, playful, or modern-mod, the winter 2025 pencil skirt is proving to be the cold-weather staple no one saw coming. Here’s how Lili Reinhart, Ella Purnell, and Zoey Deutch each reimagined the silhouette—and how you can use their looks as your personal winter mood board.
1. Lili Reinhart’s Polished, Office-Ready Pencil Skirt
Outside Live With Kelly and Mark, Lili Reinhart delivered a refined twist on the trend, wearing a rosebud-pattern Tory Burch pencil skirt paired with a crisp button-down shirt. Pointy-toe heels grounded the look, giving the entire outfit that clean, workplace-ready finish—sharp enough for a meeting, stylish enough for an event, and accessible enough to recreate with basics already in your closet.
Though Reinhart was there promoting Hal and Harper, the vibe had strong academic-rom-com energy—fitting, since she stars in the upcoming adaptation of The Love Hypothesis. Florals continue to be one of Reinhart’s signature styles (her 2021 Met Gala look is proof), and here she uses them to soften the severity of a pencil silhouette without sacrificing sophistication.
Key elements to replicate her look:
– Patterned pencil skirt
– Tailored crisp button-down
– Pointed-toe shoe
– Minimal accessories
– Soft glam hair
This is winter workwear at its most polished—and easiest to personalize.
2. Ella Purnell’s Spring-in-Sydney Pencil Skirt Remix
While the northern hemisphere bundles up, Ella Purnell reminded us that fashion is a global phenomenon. Photographed in Sydney, Australia, she wore a lightly structured, A-line interpretation of the pencil skirt—belted at the waist and styled with a halter top and sandals.
The result? A warm-weather take on the silhouette that’s breezy, feminine, and ideal for transitional seasons. The look blends Y2K elements with modern tailoring, proving that the pencil skirt doesn’t need to be stiff or strictly corporate.
Even though this outfit aligns with Australia’s spring, it’s still a perfect blueprint for early spring dressing in the U.S. when temperatures creep above freezing but tights still feel optional.
Key elements of her look:
– A-line pencil skirt with belt
– Halter or sleeveless top
– Minimalist sandals
– Warm-weather textures
– Soft, natural makeup
Save this one for March Pinterest boards or an early spring getaway.
3. Zoey Deutch’s Youthful, Mod-Inspired Power Skirt Moment
The standout look of the trio comes from Zoey Deutch, whose bold take on the pencil skirt trend embraces color, attitude, and effortless cool. Her version pairs a bright, low-slung skirt with a belt, statement shoes, and a structural top with eye-catching buttons.
Oversized Jackie O sunglasses and a fresh haircut lend the look a mod-inspired edge, while the boxy cuts keep the outfit modern, slightly androgynous, and comfortably wearable.
This styling shows exactly why the pencil skirt has staying power: it can feel youthful, trend-forward, and completely anti-stuffy with the right accessories and color palette.
Key elements to recreate the look:
– Bright or bold-colored pencil skirt
– Low-slung fit
– Oversized sunglasses
– Mod or vintage-inspired top
– Contemporary shoes (platforms or chunky heels)
– Minimal jewelry to let the structure shine
Fresh, fun, and fashion-forward, this is the version of the trend destined for street style photos.
Why the Pencil Skirt Trend Is Taking Over Winter 2025
The resurgence of the pencil skirt taps into a larger shift in the fashion landscape—one that merges professional polish with personal expression. Today’s trending pieces must do double duty: stylish enough for a night out, structured enough for an office meeting, versatile enough for unpredictable weather.
This season’s pencil skirt hits all three marks:
– It’s transitional
– It’s universally flattering
– It’s easy to style up or down
– It works across aesthetics—from soft-girl to corporate-core to mod revival
Whether channeled as ladylike elegant, spring-ready light, or boldly youthful, the Winter 2025 pencil skirt proves that some silhouettes never really go out of style—they simply get reinvented.
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