Ask Allie: How to Style Leggings with Dresses and Maturity

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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 leggings with dresses, we just need to be more aware of proportion.

Here’s some ways to wear leggings with dresses when you’re curvy:


how to wear leggings with dresses, featured by popular DC fashion blogger, Wardrobe Oxygen
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 | how to wear leggings with dresses, featured by popular DC fashion blogger, Wardrobe Oxygen
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 wear leggings with dresses, featured by popular DC fashion blogger, Wardrobe Oxygen
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.

A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

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  1. I always try to “dress-up” leggings outfits depending on the kind of shoe or by layering a blazer over them (over a silk cami or shell top). The long tunic/sweater dress combo (for me: a cold weather staple 100% I’ll be wearing winter boots with!) comes off much more polished, I feel, adding a belt and tights to complement it as a semi-formal office outfit. Maybe because I came-of-age when there was a gross trend of people publicly wearing pajamas in the mid-2000s(?), but: I think leggings were actually an “improvement” (lol!) over that really bad idea and, as long as they’re NOT painted-on-looking exercise kind or see-through-up-the-wahzoo thin, I’m guilty of considering them pants (opposed to tights: something I equate to an accessory; to avoid the improper bare leg look in a religious or professional situation).

    1. This post was written three years ago. At that time it was near impossible to find photos of plus size fashion not on dress forms or mannequins. I did the best I could with the images I could find. Luckily in 2017 there are more retailers and they are realizing the value of combining both models and white background product photos on their websites so customers can see it on a figure and websites can properly market their clothes through collages and widgets. I need to put on my list to update this post with new graphics depicting curvy figures.

  2. I think leggings with a dress look good no matter your age. It’s sophisticated and modern and as long as you are not overweight, why not?

  3. I LOVE wearing leggings with dresses and tunics all fall/winter/spring! I actually will wear an outfit like this to work on occasion, as long as it looks professional enough (although, I work in a school so I don’t need to look overly dressed up or anything). I bought some new tunics and leggings this spring on sale that I cannot wait to wear in the fall! I think some of my personal favorite ways to wear leggings and dresses are monochromatic and with boots, like you’ve listed above. Great tips, Allie!

  4. Love this post! We have (usually–not last year) fairly mild but frequently rainy winters. Leggings, a tunic in light sweat-shirt-type material, and boots are a winter staple for me. Maybe I will use this post as a jumping-off point to include more than just basic black and gray outfits in my winter rotation!

    1. I have to admit your post made me want to give it one more try. The thought of a light sweat-shirt over leggings with boots sounds so appealing! I will give it a go but usually end up with the same conclusion year after year that it doesn’t look good on me.

  5. Another Great post. I wear leggings/jeggings in the cooler months and I have to make sure that my dress covers my butt and is not too tight on my thighs. If not I cannot wear them.

  6. Good post! I am over 50 and wore leggings for the first time this year! I think the key is remembering they are NOT pants and keeping the outfit on the sophisticated side, even if casual. I am loving the comfort factor and plan to keep working on this.

  7. I think these are fantastic examples of exactly how to wear leggings if you’re over 20. (or even over 50!) As long as the top is long enough to prove that you don’t think leggings pass as “pants” then you can have fun with your outfit. This idea that some commenters are making that you might “look like you’re trying to hard” is exactly what causes older people to dress OLD. Live life and have fun!

    1. Thank you I struggle with the “dont look like you are trying to hard” syndrome dailey . Im skinny have been my whole life. I have a metabolism from some sort of science fiction horror movie, I can eat whatever I want whenever I want. sounds magical till you have to buy cloths, nothing fits ever ! I have to shop in the teens dept and that leaves jeans and tee-shirts which brings me to my point. Leggings look comfortable and trustworthy like i wont be constantly pulling up my pants. But I wouldnt know because Im to scared to try the damn things, like people may think Im trying to relive my teen years or something.

  8. This a great collection to inspire a professional way to wear leggings. I am a dress and skirt wearer and a teacher. I have to be conscious of my appearance from every angle while sitting, standing or raising my arm to write on the board which shortens even knee length items. Also, typical professional dress is difficult during the demanding and unfortunate situations of hours of windy weather while outside for bomb threats, lock downs, and moving kids quickly in response to fights. Leggings and tights have become a necessity to maintain my professional wardrobe while still functioning in my role. I am refusing to fall into the trap that is polo shirts and khakis because they do not inspire comfort or confidence, and you need both to be success in any work place!

    1. I am also a teacher and dress and skirt wearer, and like you, I believe in maintaining a professional appearance.At least your fellow teachers wear polos and khakis. At my school most of my coworkers wear jeans and tees. Do we ever need a dress code!

  9. These are great ideas for fall and winter. But how to pull it off in the warmer weather? Long leggings are too warm? Can you wear cropped/knee length leggings when it’s hot? Or simply stick to maxi dresses and rock on?

    1. I have yet to see a woman over 30 carry off knee-length leggings with a dress. I often wear shorter bike shorts that can’t be seen under the dress to prevent chafing and provide modesty, or else a longer pair with a midi or maxi skirt 🙂

  10. Great post, Allie. Even at my height, I prefer to wear my leggings with boots; even flat boots definitely cut the frump factor!

  11. I don’t care for the off-the-shoulder tunic, not because it’s off the shoulder, but because the hip hugging design over leggings looks like lounge wear to me.

  12. Your description of the willowy woman had me laughing out loud! As much as I am proud of my strong body and my boobs/booty combo, I long to be willowy.

    I have also been wanting to try this combo and am going to make it happen this winter.

  13. I’m with Aimee, after a certain age, leggings just “date” my whole look! I am all for tights, which I will wear with dresses, skirts, boots and even long tops in the fall and winter, but to me leggings kind of look foolish for someone 50+ and, since it draws attention to your legs and feet, make a heel or flat look like you’re trying way too hard to look young. But, not to say that the suggested looks you offer aren’t fabulous, just not for me.

    1. I agree with this, to an extent. I don’t find leggings as comfortable or flattering with most dresses as I do tights. I don’t like the way many leggings can bag around the knees and find that opaque tights give a sleeker look. I do have one ridiculously expensive pair that are blacker than black, totally sleek, and don’t have a bit of shininess to them but I can’t imagine spending on more colors of those.

      Basically, unless they’re really nice and part of a monochrome outfit as above, leggings read as pretty casual to me, but not necessarily young. I just turned 40 and have been known to carry a pair in my bag to pull on under a dress on cooler summer evenings, like at a music festival. I would rarely wear them to work.

  14. Boots kind of rescue outfits for me in the winter. I love dresses with tights and boots. Goodbye to worries about how to hide spider veins! For reasons I don’t understand, though tights are similar to leggings, the look is quite different. It might be just me, but I think you have to be very careful about pulling off leggings after a certain age. Even with the right silhouette it can look a little silly. I see it all the time on ladies my age (mid-late forties) and older and sometimes the outfit is adorable, the proportions are right but the look is just too young. There are exceptions of course! This is absolutely just my opinion and I am sure many will not agree. I know we are supposed to think age is just a number but in my case that number means watching out for things that are too trendy.
    Great post and outfits for those who can carry it off! Wish I was one of them.

  15. Great examples! I have been wanting to try this but couldn’t see how. I especially like the monochrome and “boots” suggestions and can see myself wearing any of those combinations. Thanks, Allie.

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