How I'm Attempting to Style Summer's Most Controversial Trend

Layering up despite the temps.

I’m #blessed to have a ride-or-die best friend who has indulged me a lot in the last 27 years. This includes but is not limited to: running away from home at the ripe age of 6, dying our hair together with box dye, and also, wearing skirts over our jeans in 7th grade.

Inspired by some Disney channel star, I’m sure, my bestie and I planned a day to both wear short floral skirts over our bell-bottom jeans to school. I don’t recall it causing much of a stir in the hallways (though I bet people were talking given the nature of middle school), but I do recall how thrilling it felt to take a fashion risk and have someone to do it with.

You can only imagine my surprise — and joy — to see that wearing dresses over pants is currently trending. Of course, I texted her and we both joked that we’d been there, done that. But as we all know, the trend cycle is cyclical and since it’s been nearly 20 years (sickening) since I first layered up my bottoms, I thought I might give it another go.

This time around, instead of throwing on a short, flouncy skirt and bell bottoms, I’m opting for airy dresses and looser denim. To make this trend a bit more practical, I’m hoping to style dresses that are currently collecting dust in my closet because they’re either:

• Too sheer to wear without a slip (as I playful said to

  Emily Grady Dodge
  “why am I buying a piece that requires me to buy another piece to wear it?!”)

• Too fancy

• Too short to wear on their own

• Too uninspiring for me to reach for lately

Here’s the inspo:

Image: Pinterest

Image: Pinterest

Image: Pinterest

Image: Pinterest

Image: Pinterest

Image: Pinterest

And here’s the results of my styling exercise.

Styling a Dress That’s Too Sheer

Starting off not strong with a fairly obvious choice. This Hill House dress (currently unavailable in white, but THB that’s probably a good thing) is not only TINY, it’s also very sheer. I keep meaning to sell it but then I get stuck on how expensive it was and throw it back in my “to figure out pile.” I think wearing it over jeans like a baby doll top á la 2006 actually works fairly nicely, despite being kinda derivative.

Styling a Dress That’s Too Fancy

This silk slip dress from Quince is my new go-to for work events (just add a blazer and you’re good to go), but I’d love to show it off at more than just a cocktail hour. The tucking here is not precise, but I like the idea of creating a different angular silhouette with the hem. I wish I had a broach or silk scarf to tie around the waist to really polish this off, but here we are.

Styling a Dress That’s Too Short

So I actually do wear this Free People dress on its own because the back is longer than the front, but similar to the first style, it works well with jeans and flip flops! I’d also love to try it with my white linen pants for a monochromatic moment.

Styling a Dress That’s Leaving Me Uninspired

I’ve had this Zara dress for a few years and it’s another one I never reach for but also can’t seem to part with. I tried wear it at its normal length with the jeans since I loved how the long silhouette looked on some of my Pinterest inspo above, but ultimately found that to be a bit too overwhelming. In a perfect world, I’d add a low slung belt and something pin up the side, but I still like where I’m going here!