How to style skirts over pants: This Y2K trend is back, here's how to wear it

Need help with how to style skirts over pants? Here's all the tips and inspiration you need

street style shots of women showing how to style skirts over pants
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Learn how to style skirts over pants this season as a way of embracing Y2K trends. With their last major style outing way back in the early 2000s, this is a look we thought had long been put to bed, but thanks to the resurgence of both micro minis and Y2K looks, skirts over pants outfits are back with a bang. 

When it comes to how to style skirts over pants, the key is balancing hem lengths and proportions. With micro minis one of the fall 2022 fashion trends, this look largely relies on short skirts, as they will balance the sudden appearance of pants under your skirt hem. You'll also want to think about the fit of both your pants and tops and use them to help streamline your silhouette. Wearing too many baggy items together can overwhelm your frame while balancing some fuller and some more fitted silhouettes within your skirts and pants combo will help to highlight your shape and your style. 

Exploring how to style skirts over pants can feel challenging, but there will certainly be pieces in your current wardrobe that you can utilize in this quest. While it's rooted in the early 2000s, this look also works with a number of the '90s fashion trends around at the moment, such as slip skirts and faded denim. There is a level of experimentation needed to nail this look, but once you understand the proportions aspect, it is one that can work for smart or casual occasions. 

How to style skirts over pants

Discovering how to style skirts over pants gives a whole new world of outfit opportunities. While not all your skirts and pants will work for this look, those that can benefit from this directional feel, instantly up their cost-per-wear abilities. A styling trick that can be used for both work and play, it's great for smart casual outfit ideas

1. How to style skirts over jeans

Ashley Tisdale from 2005 on the red carpet and a street style shot from 2022 of women in skirts over pants outfits

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When it comes to how to style skirts over pants, jeans are an obvious choice. The best jeans are cool and casual, but as a capsule wardrobe staple, we're always looking for ways to reinvent them and they're ideal for integrating into this fashion trend. From the best skinny jeans to learning how to style flared jeans, there is no denim silhouette that won't work for this ensemble, so it largely comes down to the skirt you choose. 

To render this look party-ready, look for the best sequin skirt, a short style will feel dancefloor appropriate but paired with kick-flare jeans, you'll appear more relaxed and be comfortable too. Opt for a thigh length flared skirt, over a pair of jeans that flare at the hem but remain close to your thighs to help show of your shape. Team with a fitted top to ensure that the bottom half of your look is where all the attention is. 

For a more seamless iteration, champion one of the big denim trends 2023 and opt for double denim. A creative denim skirt outfit idea, team a short denim skirt over a pair of jeans for a fun, casual look that embraces Y2K to the max. For those that are a little more daring, this look will also work for how to style baggy jeans, although this look certainly requires a more tailored and fitted top half to balance out the amount of fabric. 

2. How to style skirts over pants for work

skirts over pants

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Often with grunge connotations skirts over pants might seem like an unusual combo for the office, but with plenty of tailored iterations around, it's a pairing that adds a point of difference to your look and exudes confidence, while still feeling smart. Although you can wear heels with this ensemble, it's an ideal candidate for how to style loafers, as it adds a traditional element to proceedings.

To make this look work-ready, choose a tailored skirt and pants, preferably in matching fabric or tonally matching hues and team with a shirt, or a fitted tee and a blazer. Unlike casual options, when it comes to how to style skirts over pants for smart-wear, look for a longer knee length hemline for added sophistication. An A-line or pleated skirt will feel sharp and still directional, and worn over a pair of straight leg pants or a wide leg style if you're feeling a little more daring. 

3. How to style skirts over pants for casual

how to style skirts over pants, shown by two street style shots

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The options truly are endless when working out how to style skirts over pants for casual wear. Essentially anything goes and you are not limited by fabrication or skirt length, although proportions are still important in ensuring your frame is not overwhelmed. 

While we automatically turn to denim for casual occasions, for a more directional, outfit, lean into the fashion trends 2022 and experiment with on-trend leather pieces. An ideal moment for learning how to style a leather skirt with leather pants or thick, legging-like pants, this is an edgier interpretation of the trend, that can also be teamed with your best winter boots, for a seasonally-appropriate, trend-led ensemble. 

4. How to style pants over skirts for evening wear

skirts over pants in two street style shots

(Image credit: Getty Images)

The rise of the overskirt has made how to style skirts over pants for eveningwear a breeze. A popular wedding dress trend 2022, overskirts tend to be sheer, maxi silhouettes, worn to give wedding outfits or evening dresses added drama. Worn over a skirt, a flattering jumpsuit or a pair of silky palazzo pants, this is a fun and sophisticated look, with the comfort of wearing pants, and the adding softness and femininity of a princess-style tulle or chiffon skirt on top. As this can be quite a statement ensemble, opt for a simpler silhouette on your top half to allow the skirt/pants combo to do the talking.

Rivkie Baum
Fashion channel editor

Rivkie is a fashion editor, writer and stylist with twenty years' experience in the industry. Rivkie studied design and pattern cutting at the London College of Fashion, and fell in love with styling and journalism, and has covered fashion weeks in London, Paris and New York, as well as shooting editorial all over the world.

Specialising in plus size fashion, Rivkie has long championed that style is for everyBODY and has appeared on a host of radio stations and television shows, pushing for greater representation for plus size women and fashion throughout her career.