How to wear dresses over pants, according to 10 fashion creatives

À la Ashley Tisdale.

Now is the ideal time to confront your fear of layering, because the dress-over-pants silhouette is back. As another throwback to the iconic early 2000s era, I’m obviously a huge fan. Not only is the silhouette a refreshing break from the endless big top little bottom, or little top big bottom rotation, but it’s incredibly comfortable. 

Need to unbutton your pants after dinner? No worries – you’ve got a dress on top. Feeling a little self-conscious about your bloated tummy? Layer a dress over your pants and the problem is out of sight.

Looking for more ways to procrastinate? We’re with you. Come on over to our Fashion section. 

To prove my admiration for the dress-over-pants silhouette, below I styled a Nobody Denim dress over a pair of classic jeans for a simple, monochromatic take. If you’re not already convinced of the sheer power (and comfort) of wearing a dress over a pair of pants, I called on some of my favourite fashion creatives to show me how they like to style the look.

Georgina Taylor, Creative Director at Eethyn

I’ve always loved the sometimes questionable layering trends of the early 2000s for the way they threw the book back at traditional styling. That era was truly chaotic in the best way. I sported a lot of blue jeans and summer dresses as a kid in reverence to my favourite it girls, so it was a lot of fun to revisit this trend. 

For my take, I’m wearing my favourite pants by Song For The Mute. These are my daily [pants]; they go with everything! This dress was given to me by my sister. She bought it at a sample sale years ago and it’s a well-loved hand-me-down. 

I like that the form-fitting dress over the loose pants is a little unexpected, but they didn’t pay attention to the rules in the noughties so why should I now? I styled these over an Ottolinger mesh polo and finished it with a crocheted Poms hat, my Docs and a bag from the op shop. That’s my modern interpretation. There’s a lot of black but I live in Melbourne, what do you expect?

@_eethyn

Katharina Mildren, Designer and Founder of Katharina Lou

Styling a dress with a pair of pants seems unexpected and injects a bit of fun into the every day, so it has been my go-to this summer. I’m wearing a mini dress from my Katharina Lou collection which would be viewed as more of an occasion dress but pairing it with my Après Studio cropped flares pulls it back to a more everyday look. [They] give me an excuse to pull out the OTT items daily! I hold a lot of value in my clothing so being experimental with this trend is allowing me to wear the same pieces I love over and over again and not get bored.

@katharinalouu

Victoria Latu, fashion editor and presenter

The dress-over-pant look has been a favourite of mine for a while now. Especially when the weather getting cooler, [and] you still don’t want to give up your summer favourites. Also, there is something about throwing on a dress over pants that makes it feel and look edgier.

As a stylist, the biggest key to pulling off this look (or any look or style for that matter) is getting the proportions of whatever you are wearing right. The eye is always looking for balance. To get the best [out] of this look, you want to make sure that the waist of the dress you are pairing hits the waist of the pant you are wearing. Only then will things look in balance. This is regardless of what style you choose to wear. Try it and thank me later.

@victorialatu

Jillian Arcenas, content creator and fashion creative

Not only is the dress-over-pants such an iconic ensemble (think Ashley Tisdale circa 2000s), but it is also my favourite getup for those months of transitioning between seasons. It is an easy way to make sure your summer dresses still get some love during the colder days. 

As someone on the shorter side, this type of layering can often drown me. What I love to do is wear dresses that are short or have some sort of asymmetrical flow to the design to give the outfit some dimension. Originally a maxi, I tied it on the side to give the dress some shape, juxtaposing the straight-leg pants.

@jillarcenz

Cait Emma Burke, Fashion Journal‘s Editor

I’ve been fond of layering dresses over pants for a long time. I worked in vintage/consignment fashion for most of my early twenties and being in that environment every day encouraged me to be pretty playful and carefree with my style. It also made me very referential – when you have easy access to a plethora of incredible ’90s and early 2000s pieces, you inevitably start referencing those eras.

As my style has evolved over the years, I’ve continued to pair dresses with pants. I find that it adds a point of interest and depth to an outfit, and as someone who is permanently bloated (didn’t you hear, IBS is a hot girl thing?) it’s also an incredibly comfortable look. For Melbourne Fashion Week, I layered this Suku T-shirt dress over a pair of black vintage flares. As it turned out, it was the outfit I felt best in all fashion week – probably because I felt so bloody comfortable.

@caitemmaburke

Anna Golka-Yepez, online fashion stylist and creative

I’ve been wearing dresses and/or skirts over pants for a hot minute now. I love this styling technique because it’s a way to breathe new life into your pieces. Everything gets double the wear with this layering. I also think it’s just so chic and bold. I’ve styled it casually but paired with a fancy pair of trousers and a beautiful dress, this is a look that I love to make work for any occasion.

@annagolkayepez

Phoebe Kelly, fashion stylist

As an adolescent, my outfit of choice was always a dress. Preferably a shade of pink with a sweet embellishment and I was ready to present myself to the world. Progressing to my twenties, it’s very much [a] The Sisterhood of the Travelling Pants moment for me. Pants are always practical and have me feeling put together. 

The dress-over-pant trend is one I absolutely abide by! For me, combining the two brings a sense of nostalgia whilst simultaneously looking chic. The beauty of layering a dress over pants is the transseasonal element it brings. Your summer dresses and winter pants can now be worn all year round. This trend just added years to your wardrobe’s lifespan.

@phoebe_kelly

Matisse Laida, multidisciplinary creative

The dress-over-pants trend in the early ’00s was so very chaotic that I never really got the hype when it came back. However, I’ve been dressing less hyper-femme recently, and a skirt and pant combo gives me very non-binary energy. I love how the trouser adds a masculine texture to an otherwise very femme outfit, so wearing my matcha Romantics custom piece with an old pair of black pants and suit jacket was the perfect pairing that made me feel ultra-comfy but also very sleek and sophisticated.

@your.never.girlfriend 

Jacqueline Alford-Crofts, content creator

I’m so glad the dress-over-pants trend is coming back, it’s so nostalgic and reminds me of what I wore as a kid in the ’00s! It can make a regular outfit look super elevated and different, it’s easy to thrift or find in your own wardrobe and no two people will wear the trend the same. Especially with winter returning, adding that extra layer of warmth is essential but it’s still giving fashion girlie hottie energy.

@jacquialfordcrofts

This article was originally published on April 26, 2022.

For more on the dresses over pants trend, try this.