Ask Allie: How to Style Leggings and Dresses with Maturity

Fashion Advice

I'm 41 and a curvy girl. I'm also 5'4″ on a good day. I'm proud of my curves. I like the look of shorter dresses with leggings underneath. How do I wear them without looking “too young” or too short/frumpy?

Oh how I love the look of a willowy woman in a tunic or shirt dress, black leggings and ballet flats; such a chic yet simple look for running to the grocery store, slipping on something for a latte after yoga class, meeting friends for breakfast on a Sunday morning. And every few months I try this with a dress that accidentally went in the dryer and my Ecco flats and realize, I am not willowy and such a combination makes me look as though someone cut me off right below my calf muscle or if I was headed to Twin Day at my daughter’s kindergarten class.

That’s not to say us curvy shorter women can’t rock dresses with leggings, we just need to be more aware of proportion. Here’s some ways to wear leggings and short dresses when you’re curvy:

how to wear leggings with short dresses
shop similar: printed dress | off the shoulder tunic | military-inspired tunic

Leggings with Sophisticated Silhouettes and/or Prints

The quickest way to look too young is to wear something that a child could carry off. Leggings with a babydoll or empire waist dress, an oversized sack, or something in calico or a very girly print can give the wrong vibe. Consider graphic prints and classic stripes instead florals or polka dots, mature details like military accents, belts, or showing a bit of skin with an off the shoulder silhouette. By choosing an obviously adult print or silhouette, the leggings look less like something for the playground.

how to make leggings look sophisticated
shop similar: short sleeved tunic | short necklace | roll-sleeve tunic | scarf | sleeveless tunic | long necklace

Leggings with a Monochrome Ensemble

Leggings look more purposeful and create a figure-lengthening look when the same color or color story as the rest of the ensemble. Choosing more adult colors like navy, olive, black, gray, brown, and cream separates you from the kids at the playground. When the dress and the leggings are the same color, the look is cohesive and also looks far more adult and sophisticated. Use accessories to add interest and personality.

how to style leggings with tunics or dresses
shop similar: gray dress | ankle boots | printed tunic | tall black boots | camel dress | necklace | suede boots

Leggings with Boots

Whether they are ankle boots or up to the knee, slipping a pair of boots over leggings adds volume, balancing the figure and reducing the frump factor. This past winter I regularly wore my navy sweatshirt dress with black leggings and tall boots and it looked far more adult and flattering than wearing the same look with flats. Boots also toughen up a look to keep it from looking too twee or childlike.