What to wear with skinny pants and leggings?
Skinny pants, leggings and everything in between. What’s the difference, are they age appropriate, and what do you wear with them so you don’t look like a giant ice cream cone? Here’s our thoughts…
Skinny pants are just that- pants that are close to the body and narrow at the ankles, sometimes even hugging the ankles. The newest versions have some stretch.
Leggings are more like tights. They fit very close to the body and end at the ankle, or mid calf. The biggest difference is that they are more lightweight than a skinny pant- almost like a thick stocking.
A good way to think of it is: leggings are an accessory. Don’t wear leggings as pants.
You can wear skinny pants with short tops, t-shirts, short sweaters and long sweaters.
You should only wear leggings with long tunics, long sweaters, long jackets, long shirts and short, but not mini dresses that are ultra short. In other words, if you are wearing leggings, don’t expose your behind. Cover it up. Take a look at what we mean…
| Long Cardigan + Skinny jeans or leggings:
This is our favorite look with leggings or skinny pants. Everything is so soft and flowing and looks so right. Black leggings are very slimming and work best in fall, winter and early spring paired sweaters. Don’t ever wear them with a t-shirt, or it will look like you lost your pants. |
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| Boyfriend Jacket and Leggings:
If you wonder whether leggings are age appropriate, get a load of JoJami’s mom (age 70!) She rocks this look. |
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| Shirt Dress + Leggings:
A shirt dress is long and would look really good over leggings. You can add a great belt and big chunky fabulous necklace to perk up this look. We find it quite drab the way it is. |
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| This gal has the idea:
A long to and jacket over leggings and ballet flats. Very cool. All black makes you look taller and slimmer. |
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| Wear leggings with a short (not micro mini) dress:
This dress is a good length to pair with tights. It looks like a tunic. Take a look at some other dresses we blogged about that are similar and would work with leggings. |
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| Leggings with a skirt:
JoJami looks great in this column of color with a skirt overtop that also has a lot of black in the pattern. The necklace also co-ordinates. See, you can wear leggings and look good after 40, 50 and beyond! |
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While we were writing this post we heard from a subscriber who sent us a picture of an outfit she had that she was wearing leggings with, and asked us what we thought. Here is the picture ( on the left) and here is our answer….
Answer: Thanks so much for sending us your photos. You are so youthful looking for your age and still have a terrific figure, wow! However, we are going to vote no to this outfit for several reasons.
We can see that you are trying to make this outfit age appropriate by adding the leggings. However, although it does make the outfit a tad more modest, the problem is that your sending the signal that you are still trying to dress too young.The basic jean mini-skirt and printed t-shirt are saying “teenager”.
If you want to look up to date and stylish, you can wear the leggings with a long top or shirt dress. (see above)
The white sandals are trying to tie the outfit together but is not working either.
We think you need to trade in the skirt and t-shirt for a pair of Bermuda shorts (above the knee) and a fitted “v’ neck top and different sandals.The white sandals you have on will work nicely with a colorful sundress that has a white background. Good luck!
After this reply our subscriber sent us another picture of her in a black and white bandage dress and asked if she could wear leggings with this. Our reply was no because the dress was too tight for leggings. Leggings look better with a looser top or tunic.
Finally here’s a picture of a gal in blue we pulled out of our files from a party we went to. This gal is wearing a short skirt and dark stockings in summer. They don’t work.
The skirt is too short for someone over 40, whether you wear leggings or stockings. Also this is a summer outfit and her leg covering are too dark for summer.If they would have been black leggings they also wouldn’t have worked for the same reasons.
Bottom line- don’t wear a micro mini after 40! You will look silly.



















My problem is being long waisted and full in the hips and thighs, creating the dreaded pear shape. How do i pull off this look without emphasizing the hip area?
And why do department stores carry soooooooooo much that is too low cute and too trendy for 50′s?
There are lots of leggings and skinny pants… but the main concern for us over 40 gals is QUALITY~
Leggings are thin and need to be made of the thickest of material.
Skinny pants need to fit properly and not be too too tight. All the stores have them…and on line does too. Your budget will have to drive what brand you buy.
Love all your fashion input, however, I am having trouble finding skinny pants and leggings. Any store suggestions??
HI Lalita,
Well, blue jean skirts are really not that in style right now. Instead, get a blue jean jacket and pair it with a skirt or fun colorful pants. We sugest that you retire your long bluejean skirt it will just make you look dated and frumpy.
What about a blue jean skirt that comes to me knee with leggings and short cowboy boots?
I love wearing black leggings with all of the looks you show. I have always worn TUNIC style tops, just because I find them very flattering with flats or heels. My only question is about wearing blue jean denim skirts. I live in Texas and find it necessary to stay cool. I do wear appropriate sundresses, but when it comes to wearing shorts, no way. I am thin, but do not care for any shorts on me. So, in turn, I use a denim skirt to wear with flat boots and usually a black simple shirt or top. I’m 50, and feel more comfortable in my blue jean denim skirt than khaki shorts.
Hi Reese,
Welcome to the 40 club! We are not here to put a crimp in your fun or are trying to tell women to dress matronly! Just the opposite, we are trying to help women put the fun back in their wardrobe. However, we do encourage dressing “age-appropriate”. What does that mean? Well… you say that your friends say that “you look ‘teenager’y”… we say, send us a photo and we will put it up and let you know how you look and and get our readers to pipe in as well! Hope to “see” you soon!
Ok, here’s a question. I AM 40 but still get carded at the bar. I was at the mall the other day and realized I was dressed pretty much the same as every 20-something girl in the place. I was getting some nice smiles too (blushing). My friends always say I look “teenager-y” but they also say they wish they could still fit what I wear.
Why should I stop dressing young if it works? You are only as old as you feel and dressing like your old will only speed up the process. Don’t get me wrong, I have plenty friends over 40 who LOOK over 40. I agree with you points in that case completely.
Just my thoughts
Thank you for a great post. I love leggings and skinny jeans and think they are a good way to update a wardrobe for those over 40. Modern yet still modest!
Dear Fabulous,
Just had a look ,and i am impressed ,wonderful advice and style tips.
I will be checking in regularly from now on for some classy details.
Love the website.
Liz
I love this post! It really gives me some ideas for wearing tights! I think they are very slimming! ♥
JoJami & Jojami’s mum both look terrific in their leggings. Very nice indeed.
Hi Cindy,
Thanks for writing in! Our aim is to empower women and let them know that, “Life is too short to be frumpy!”… in other words, lets not give up on looking chic and hip just because of a number! Glad to hear that you are already doing that and we encourage you to keep on!!
We went to your site, http://www.laferle.com and enjoyed reading your article about shopping for vintage clothes. So, from one fashionista to another, we applaud you!!
Thanks so much for this post! I have been cautious about wearing leggings, and typically wear them with longer shirts and tops, just as you suggest, and I do enjoy the look. I often get compliments from women my age who tell me they never thought of wearing leggings again … so I always wonder if I’m overstepping my limits.
As I’ve written to you earlier, I often find that most fashion books and/or magazines are oblivious to women over 40. And if they pay attention to us at all, it’s usually to give us a long list of things we should NOT wear, leaving us few choices and making us feel like giving up … But you ladies rock!
Hi Meg,
Ok. you got us thinking! I (JoJami) have not stepped foot into a Chico for years (and I am 50)… I will give it a try and do a blog post on my findings and photos! When I have tried to shop there in the past, I found everything I put on made me feel matronly.
Thanks for calling us out on it… how can we bash a place we have not been in for a while!!!
Hi Ruth,
White House Black Market have a great really good fitting pants. Also, depending on your body type, the higher end brands like theory and Ellie Tahari.
We will have to do a post about your last question, but a quick answer is to do a soft fabric blazer and make sure the khakis are great fitting. The DKNY site has some really nice examples and good fitting pants as well!
On the subject of where to go for clothes–what about those of us who like to wear preppie. It is such a clean fresh look but I am having problems trying to find pants/slacks that fit nicely without being too baggy or tight? Any suggestions?
And what would you sugest to give a modern twist to khakis, tees and blazer?
Thanks for the great tips. I’m always afraid to wear leggings, and I always end up taking them off. One time I did wear black opaque tights (the panty hose that cover the entire foot) with a short dress and black high heeled pumps. It seemed like an OK outfit at the time. The material was thinner then leggings, though. I think it is best to wear leggings if you have thin legs.
Come on. I don’t know what your gripe is about Chico’s. They have great stuff for all figure types. I often wear their clothes as they have lots of separates I can wear with other items and I AM NOT heavy!!!
Hi Anne,
Yes, if you are tall, that is a look that you could pull off. One concern is that the top of the pant be more fitted. If you try to wear a full pant like from Chico’s over a dress, they tend to give you the “TENT” look. If you want a fuller leg, keep the fullness in the form of a “flair” pant, not a full pant.
Chico’s dressing is really ment for those women with fuller figures. So depending on your body type you have to be careful where you shop. If you have a fuller figure we would recommend http://www.lolaandgigi.com, over Chico’s.
If you have a slimmer figure, you should stay out of Chico’s!!! Break out and try a new store!
Cheers,
The Glam Gals
Hello dear ladies
I’ve looked with great interest at your suggestion: short dresses with sleeves worn over leggings or slim pants. If you’re tall enough, would you recommend wearing that kind of dress over wide-legged, flowing pants (a bit like the Travelers Pants from Chicos or TravelSmith -can’t remember which)
I agree about denim mini and leggings. No one over 21 should be caught in tht. It’s a definite teenage girl thing and grown women NEVER, EVER want to copy teenage girl looks. A great alternative might be a black casual mini dress over leggings like this http://www.overstock.com/Clothing-Shoes/Angie-Womens-V-neck-Dolman-Sleeve-Printed-Dress/4822532/product.html?rcmndsrc=6
I think this is funky, in a sophisticated way and very appropriate for an adult woman. I purchased it today!
Wow! JoJami and her Mom both look FABULOUS! I’d like to know more about JoJami’s skirt….
Yes I so agree. Denim mini-skirts (with or without leggings) after about 35 are a definite no no. It doesn’t matter whether the bod is fab, it’s just too try-hard.
Hi Angie,
Your girlfriend must not be aware of how she is coming across.
You can always share this blog post with her and then she might have an “a ha”moment! Moreover,she might see what she looks like when she sees the “bad” photos and have her eyes opened. Not only that, we even have examples of alternative ways to dress!
Good luck! At her age it is def. time to start dressing classy and chic instead of too young!
How do I get my GF who’s 39 to ditch the teenager clothes without coming off as preachy? All her clothes are too tight, too small and too young. She was in a micro mini memorial day and got very defensive when I raised my eybrow at the skirt.
Hi Lesa,
Great question…. if you are a little overweight it can be a lifesaver! You can wear a loose dress and add the leggings and heels and feel fantastic! Just make sure the dress has enough black, brown or grey to make the dark color of the legging work.
I get the part about not showing your behind, but what about wearing this look (especially skinny jeans) if you are a little overweight? Can it still work?