Regular readers know I’m a fan of leggings for their comfort and versatility, but they’ll also know that I’m a stickler when it comes to styling them properly so that you look classy and feel confident wearing leggings over 40.
Leggings are lighter and thinner than skinny jeans and pants, so they’re more revealing. Because of this, you need to have some long tops to wear with leggings. By long I mean, long enough to cover your bum and your crotch. This is true at any age and particularly over 40.
If leggings are a staple in your wardrobe, give them an update with these cute tops and on-trend accessories. And if you haven’t tried leggings yet, these lovely long tops to wear with leggings may be just what it takes to get you on the bandwagon.
What to Wear with Leggings
1. A Zippered Tunic
Tunics are popular and pair well with leggings, and anything with a zipper looks very sporty and modern.
2. Asymmetrical Tops
Asymmetrical tunics that are higher in the front than the back or angled in the front and longer on one side are a little edgy and add a touch of drama to leggings or skinny jeans. This striking purple high-low tunic looks classy but edgy with faux leather leggings and these gorgeous black suede booties.
3. Long Shirts and Blouses
For an elegant look, take a long, button-up shirt and wear it untucked over leggings. This chic striped shirt looks sharp with black leggings, a black leather bag, and suede pointy-toe flats.
Style Tip: Here’s an idea for what to wear with leggings. Some of the best long shirts to wear with leggings are shirtdresses. Many times a shirtdress will feel too short to wear alone, so pair it with leggings for a chic look.
4. Long Sweaters
One of the best long tops to wear with leggings is fabulous, oversized statement sweater. This chic black one has a flattering shape and interesting texture that makes you look wider up top and super skinny on the bottom. Leather leggings add an edgy feel, and these cool snakeskin mules work beautifully with this urban gal look.
5. Long Tees
A long tee worn over leggings is cute and casual in summer. Layer it with a jean jacket for a weekend look. In winter, a faux fur vest or a long menswear-style vest can be layered over a long-sleeved tee or sweater + leggings to create texture and interest.
Tops to stay away from when wearing leggings:
Short Tops That End at the Waist
Short tops never work with thin leggings. They can work with thick leggings, but that’s really only on twenty-somethings with rock hard abs, legs, and behinds! Yes, I know you may be in great shape, but a top that covers your bottom is much more elegant and sophisticated over 40. You don’t want to look like you are desperate to be a teenager.
Baggy Tops
Keep in mind that there is a difference between a full top and a baggy one. If you wear a chunky knit or long shirt with leggings, make sure it is the right size. Your top should sit properly on your shoulders, and the sleeves should not hang way down past your wrists. A little volume can look cool, but baggy is just plain sloppy.
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Although I love your site with ideas, why do you use size zero models to show the clothing. Plus size clothing should be on plus size models!!!!
Hi Diana, Thanks for writing. I understand your frustration. Here’s the problem. I show clothing from various stores and have no control over the models the stores use. I would like to see more mature models, plus size models etc but I have to use what models they choose to show the clothes on. If there is a certain store that uses plus size models and you like the clothes, please let me know and I can see about featuring them. All the best! Cheers, Deborah
Love this article; covered much
needed topics .. good work– good
Good info..
keep it coming Thank you
I love leggings. I have a pair of black ones and a pair of brown ones. They are really heavy knit – hold their shape (never bag at the knee or in back no matter how many hours I wear them) and are very warm. I treat them like tights – if my top isn’t long enough to wear over tights then it isn’t long enough for my leggings. I like them to come to the top of my foot and I wear them with boots – ankle, to the knee, or over the knee. I would never want any skin to show between a shoe and a legging. I do not wear them when it gets warm. I also have 2 pair of denim leggings and I love those most of all but I apply the same rule as knit leggings. They look good with a more casual top. I am only 5′ tall and one trick I have learned is to wear black boots with black leggings and brown boots with brown leggings. This way, even if the boots are short, I get a longer leg line.
I finally bought some thick dark leggings last fall and several long sweaters. I wore them once and that was that! I’m pear shaped, so all the sweaters and tops that are long either fit in the shoulders, bust, neck, etc, but span my hips (tighter) If I purchase items to fit my hips/thighs they are huge on top. Plus, having a horizontal line going across my thighs isn’t flattering. I like the look of leggings I just don’t like how I look in the outfits. Now I have a bunch of new sweaters that I don’t want to wear, and it’s too late to return them. What’s a pear supposed to do? I’m 67, 5’4” and usually, in a shorter top, I wear a small.
Hi Wanda, I’m sorry you have been having so much trouble wearing leggings but you still should be able to pull off this look with these tips. Make sure you wear something that is long enough to cover your crotch and ends some below the widest part of your hips so you don’t look broad across the hips. An asymmetrical tunic can help soften that harsh line too.
It sounds like you also need a top that is fitted properly in the shoulder and a little flowier at the bottom than you have been wearing. Think tops with a bit of swing. The next thing to do is layer your top with a jacket of some sort or shirt to add volume up top. Make sure this layering piece nips in at the waist to give you shape. As far as your leggings go, make sure to avoid showing skin where the leggings end at the ankles so you create a long dark line and look taller. Finish the look with a chunky heeled bootie to balance out your hips. Finally, you will also want to draw the eye towards your upper body by wearing an eye-catching necklace and earrings. A v-neck or scoop neck helps with this too. If you don’t like the look, don’t sweat it. You have to feel good in what you wear because clothing confidence is everything. Try something else. All the best, Deborah
I I am a slim petite 60 year young lady, & i find it difficult to get nice fashionable clothes as im small , i do like leggings & nice tops but like them to be 3 quarter sleeved, , would love to see more for petite ladies.
I LOVE this site! My problem: I’m underweight, and it’s not a choice. (and no I don’t like it) I’m 45 yrs old, 5 5 and 113 lbs- struggling to gain my 10 lbs back. I love ALL these styles, but find that because I’m small on top and thin, long shirts make me look like a stick. I wish you could come to my house and help me put clothing together – LOL. I’m not at all fashion savvy, but really try…….
I run a successful on-call babysitting service in the Napa Valley, and would like to look more professional at the Chamber events. Also, a little more put together in general… sigh…… Your suggestions are absolutely amazing. Your an artist!!! Wish I had the knack!
J. Jill and Sahalie have nice long tunics, even for us tall ladies.
Hi Deborah, just wanted to thank you for such a wonderful site. I have recently hit the 50 era and am happily on the shorter and thinner side of the scales. However I have noticed that unsightly tummy bulge thing has begun to happen along with the hot flashes. Leggings and tunics, dresses, menswear shirts, etc, are just the ticket for hiding all the fun my body is having with me. I did purchase 2 very nice pairs of leggings/cigarette pants recently from Marshals. 1 is made by Ivanna Trump (retail $168.00) , the other are Romeo & Juliet (retail $179.00) , I stole them both at $16.00 each. The plus side to them is they are very chic and they have nice tummy tuckers.
Keep up the amazing work on your site. I am also back in the retail work force and am constantly answering questions regarding what is appropriate attire for the cresting the hill chic.
Hi all. We just launched our website with the perfect tops for leggings. http://www.aliandedi.com. We are a grass roots company founded by two moms (ali and edi) who are over 40 and needed wardrobe basics with flair. Check out our Audrey top, the perfect high low top for leggings. In addition, we have tunic tops, tanks and cowl necks all with the theme of dressing with no stress. Our garments are Made in the USA.
I love your site Deborah.
Regards,
edi
Ooh. Just got a better look at the bags. Uh oh. Now I have a new quest! ?
Think I wrote you on this subject!? The problem is not the arse, but the crotch. Let’s be honest. That uncomfortable “checked out” feeling. We all know it: first men look at your eyes, then your “girls”, then your crotch. Ewwww. Makes me feel icky. So I am ever on the quest for the perfect long top to cover the FRONT.
I like the dress idea, but every one I tried looks like — a dress on top of leggings. Screams “mismatch”! Although I like the one you found. Guess I haven’t gotten lucky yet.
Not going for the turtleneck. Roast, roast, roast.
Like the asymmetrical stuff, but don’t like it when they do the color blocking thing with it.
Hi Kathy, one more point about the long top. A longer top over the leggings is also more flattering because of the proportions. If you had a top that ended at your waist your body would be cut in half which isn’t as flatter ing as 2/3, 1/3 proportions. Cheers, Deborah
I love some of the outfits you put together, and your page indicates we can “shop this look.” Do you give ideas for where you shop? I prefer to shop online.
Thank you.
Hi Mishele, You must have the ad blocker turned in your computer because beside every shop the look are tiny photos of the items that you can click and buy.Turn off your ad blocker to see them.
Thanks for this post! I absolutely love leggings — they are cozy, comfortable, and slimming when worn with the right top. And you’re totally right about wearing dresses with them. I love the look of a short dress with leggings and booties or boots. I can’t wear a short dress otherwise (ugly knees) but the leggings disguise the problem.
I see a lot of younger women wearing leggings as if they were pants — and regardless of the shape of the bottoms. Ugh. No matter how cute you think your butt is, leggings are NOT pants, ladies! That applies to all ages, in my book, unless you are a dancer on stage.
Lol! This makes me think of Anita Renfroe’s song Those Ain’t Pants – https://www.youtube.com/watch?v=MDQ5-zIUbbE
Thank you for the video – that was fun! However I do think that, as Deborah says, we can wear leggings if done appropriately with long tops and nice footwear. Of course they should be high quality too. Not the kind that are made from thin fabric, and tend to pill or pluck easily. I have a black pair that I wear with high boots, a long blouse with belt, adding a poncho when I go out.
I am 33 and I love this website. I dont think that you have to put an age on this website. You should want to look classy and sophisticated at any age, and hit it right on! Go Deborah! and thanx a million for your help, I needed it!
Hi G., Thanks for that lovely compliment. I appreciate it because I do put an emphasis on looking classy, rather than age-appropriate. I think when you dress in with elegance in mind, you will look fabulous no matter what your age. Glad to be of help! Cheers, Deborah
These are fabulous ideas! I recently purchased some leggings and have been shopping for longer tops so these are great! Thanks
Ok, let’s get down to brass tacks here. It’s not the butt that needs to be covered in yoga pants or leggings/jeggings. It’s the front “nether” region. The reason these pants are being banned is cuz of the infamous “camel toe”. Now, they have taken to the hi/lo style, which means shorter up front, draping down in back. I think Deborah’s choices are better.
Love the grey asymmetrical top. Have one similar in green must get it out of storage. I don’t tend to wear leggings but I do wear skinny jeans.