Best Long Tops to Wear With Leggings: 5 Outfits!

Regular readers know I’m a fan of leggings for their comfort and versatility, but I’m also a stickler when styling them properly. Leggings are lighter and thinner than skinny jeans and pants, so they’re more revealing. This means you need a few long tops to wear with leggings included in your basic wardrobe.

The best long tops to wear with leggings cover your bum and your crotch. A longer top will make you look classy and feel confident wearing leggings over 40 and beyond. Here are a few styles of tops that work well with leggings and outfits to go with them.

Leggings - White shirt with with Striped Tie

white shirt

1. Long Shirts and  Blouses

How do you make leggings look casually chic? Just add a button-front blouse or shirt.  This classic white shirt with the modern front twist is perfect for leggings.   Pop the collar, add some sporty white sneakers, and you have a casually chic look. The bright yellow bag adds a touch of fun.

Leggings - Blue Tunic

2.  Tunics

The nice thing about leggings is they work everything from knits, too much lighter fabrics. This cute jersey tunic with the feminine bell sleeves is soft and comfy. Pair it with black leggings, comfy statement sneakers, and a great designer bag for a great casual weekend look.

Leggings - Sleeveless Animal Print

animal print top

3. Asymmetrical Tops

Tops with off-kilter hemlines give leggings a more artsy, creative look. This summery animal print high-low tunic looks fun and adventurous in these distressed jeggings. Add a pair of leather and rope espadrilles and this safari-style saddlebag, and you are ready for the warm weather.


Leggings - Red Turtleneck Sweater

4. Long Sweaters

Long sweaters naturally lend themselves to leggings, creating a comfy, cozy look. I love this gorgeous red one for the color and the beautifully rounded hemline. Stretchy, black leggings look great with this textured sweater and add an edgy vibe. Team this outfit up with a sporty zip bag and some sleek, tall leather boots for a vibrant weekend look!

5. Maxi Tunics

A flowy maxi tunic is another fabulous top to pair with leggings. This long, sophisticated, semi-sheer tunic is a great layering piece over a tank and leggings. Wear it with black pumps for a special night out, or by day with flat, strappy sandals.

A Final Note – 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 Ponte leggings, but mostly 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 crotch 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 head 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.

Join the Conversation

32 thoughts on “Best Long Tops to Wear With Leggings: 5 Outfits!

  1. Would love it if you featured clothes us single women who are struggling to make ends meet could afford.

  2. 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!!!!

    1. 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

  3. I love leggings. I have a pair of black ones and a pair of brown ones. They are 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 two pairs 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.

  4. 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.

    1. 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

  5. I’m 55 and love my leggings. Problem is, I can’t wear them because I can’t find shirts to match. Nine pairs of wild colors, need long solid shirts because I don’t like to show my butt or my bra straps. What and where can I find them?

  6. 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.

  7. 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!

  8. 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 Marshalls. One 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 workforce and am constantly answering questions regarding what is appropriate attire for the cresting the hill chic.

    1. Hi Tammy, thank you very much for dropping by and for the lovely compliment. I find tunics are great as well as especially on those days when my tummy is bugging me or I just want to be comfy. I’m so glad you are enjoying the site and it seems like we are on the same mission – to help women tweak their chic and not fall into a frumpy rut just because aging can make dressing a wee bit challenging. Cheers, Deborah

  9. 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.

    1. 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

  10. 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.

    1. Hi Mishele,
      If you click the tiny photos of the products under the words shop the look it take you directly to the stores that sell these products to buy. Try it!

  11. 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.

      1. 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.

  12. 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!

    1. 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

  13. 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.