What To Wear With Skinny Jeans and Leggings

There’s been a lot of confusion about what to wear with skinny jeans and leggings. Many of you have emailed to ask what the difference is between the two and whether you should wear the same kind of tops with leggings that you would wear with skinny jeans. So here are some general guidelines.

legging vs skinny jeans

Skinny Jeans vs. Leggings – What’s the Difference?

Skinny jeans are tight pants that narrow at the ankles, often hugging them. The best skinny jeans have some stretch built-in.

Leggings are more like tights or thick stockings. They are very soft, stretchy, and form fitting to your body and end at the ankle or mid-calf. They are also much more lightweight than skinny jeans.

Can You Wear the Same Tops You Wear With Skinny Jeans with Leggings?

Since skinny jeans are considered pants and leggings are an accessory, what you pair them with is different.

Jeans are heavier and thicker and can be worn with short tops. Leggings are thinner and lighter and should be worn with a long top to cover your crotch and your bum. For example, you need to wear a shirt, long sweater or tunic with leggings, or else you will reveal too much information, especially after 40!

There is also something called jeggings, a cross between a legging and a jean. They are skinny jeans with a lot of stretches. If you have a good figure, you can sometimes wear jeggings with a shorter top.

The line has become blurred with so many slightly different styles of skinny jeans and leggings. A good mirror is your best judge.

Check out this post I wrote to understand what tops to wear with leggings. Just keep reading to find out what to wear with skinny jeans. 

What Top to Wear With Skinny Jeans?

Skinny jeans can be worn with short tops, short t-shirts, short sweaters, long sweaters, tops, and any jacket.

purple skinny jeans and a gray jacket Look #1  – BLAZER + SKINNY JEANS

Love colored skinny jeans but want to look grown-up? Try adding a jacket to give your outfit the polish it needs. A coat in a neutral color such as white, black, or gray helps ground your look. These jeans become more of a pop of color and not the whole outfit. Top off your look with cute pumps, and you have a sophisticated but casual daytime look.

vest with skinny jeans Look #2 – VEST + SKINNY JEANS

If you are still stumped about what to wear with colored skinny jeans, then you might want to try this idea. Look at how cute this outfit look looks for shopping or meeting friends. This gal has paired skinny jeans with a pretty blue blouse, a sporty vest, a fab bag, and menswear slippers. She looks comfy and casual and ready for action!  

The vest is an excellent way to add a little structure. After 40, we can look a little round and soft, and wearing the vest instead of the blouse alone gives us a crisper, more pulled-together look. Another type of vest you might try that has been prevalent is a faux fur vest, or you might even want to experiment with a zip leather vest for an edgier look.

black leather jacket with animal print skinny jeansLOOK # 3 – LEATHER JACKET + SKINNY JEANS    

This is an excellent option if you have ever wondered what to wear with skinny leopard jeans. This gal has paired hers with a black and suede leather jacket. This works well with the sexy playfulness of the pants. She has finished off the look with smooth suede leather booties.

This looks casual and a little edgy. I love the pop of color in the necklace that ties the look together. If you want to wear a leather jacket with leggings, just wear a longer top that covers your bum and goes to the top of your thigh.

leopard print top and skinny black pants outfit



The nice thing about a long top legging is that it works with skinny jeans and leggings. If you are wearing leggings or you’ll want your bottom covered even if you wear jeans, then go for this look. This top is lovely because it follows the lines of your body but is not tight or baggy.

It’s a good length, and the V-neckline is very flattering. A V- neckline or scoop neck top should always be your first choice because it shows some youthful skin and elongates the slimming neck.

The leopard pattern is fun and a little sexy. It’s an excellent way to wear black as all black around the face can be harsh at 40, 50, and beyond.

What’s your solution for what to wear with skinny jeans or leggings? Send a photo to I would love to post it.

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60 thoughts on “What To Wear With Skinny Jeans and Leggings

  1. I’m 46, wearing black leather trousers with an ankle boot— louse black to cover my bum. But I’m wondering about the shape of my legs. Simple chic modern, but I’m worrying. I’m only 5 ft. petite. I don’t want to look daft.

    1. Hi Heather, If you are petite, ensure your top is not too long. It should cover your crotch in the front and bottom in the back, but for a little, you don’t want it hanging down to mid-thigh. It will make you look stumpy. I hope that helps. Oh, and some booties with a chunky heel at least a couple of inches will help. Thanks. Deb

  2. Help! I’ve been looking for chambray tunic-length shirts to wear with leggings FOREVER! It seems they are either too short or too baggy. I’m 5;7”, so not overly tall. Any specific suggestions?

    1. Hi Lizanne, Why don’t you look for a chambray shirt dress? I’m 5’7″ and that’s what I wear over leggings. Shirt dresses are most often on the short side- too short for me to wear as a dress but perfect to wear as a top and a shirtdress has a straight cut, so I belt it. Hope that helps. Cheers, Deborah

  3. Great post with helpful information. Jeans are my favorite outfit. I prefer to wear tees or a loose blouse with jeans.
    Thanks for sharing the information!!

  4. I have always loved skinny jeans, but recently I realized that my hip would be fat, and now it s I feel a little bit uncomfortable wearing them. Can you help me have any other category of jeans that would be perfect for me looks like skinny jeans, and I will feel comfortable,

  5. Where can I find jeans, capris, skinny jeans, and so forth for women with larger thighs but tiny waists? If I find one that fits my thighs, they are huge on the waistline. If they do the core they are way too tight on the legs. I am a size six.

    1. Consider having your jeans tailored a bit. It’s much easier than finding the perfect pair off the shelf. A good tailor or seamstress can nip in the waist. You’ll look and feel fabulous.

    2. I’ve had that problem my entire life with jeans, regardless of brand, stretch, etc. My best solution is an excellent tailor to custom fit the waist. Most are very reasonable. I know it’s a bothersome pain, but worth it.

  6. I am 62 years old, 5’2. I weigh anywhere between 99 # – 104 #. I have cancer, but I feel great and still want to look good. I love the feel of them. I look a little bit too thin, but I wear silky long johns and bulky long sweaters ( for warmth). I add a scarf to match the leggings or jeggings. I like wearing flat shoes, but I like socks. My daughter says I should not. I wear boots too but prefer flats ( any suggestions? ). I have always taken pride in how I look ( classic casual). I am a little OCD about making sure everything matches too. For me, comfort is what I want at home, shopping/lunch, or the clinic.

    1. Hi Janice, You sound like a wonderful woman with a very positive attitude and a love of fashion! Since you like flat boots, I’d suggest you try a pair of tall riding boots. Riding boots are a classic. They look great with skinny jeans and leggings and will help balance your look if you are wearing a chunky sweater up top. They are also generally very comfortable, so look around and try some. I especially like the ones with a bit of gold hardware on them. It adds a touch of elegance.
      Best Wishes! Deborah

  7. Great article! I love how you summed it up. Pictures always tell the story, so that was a bonus. I’m 63, 5’8”, 150 lbs, and always wear longer tops to cover the business!

  8. Great post! If I were to describe the difference in a nutshell, I’d say the one represents pants, and the other does not. The latter needs cover-up and the skinnies not! A designer and stylist once said, “remember that leggings are not pants.” If we treat them accordingly, it should be easy to style them. If you don’t walk around in tights only, you can’t walk around in leggings without some cover.

  9. What are the rules for wearing boot-cut leggings or flare leg leggings? I am 73 and still haven’t had the nerve to wear leggings. I am tall and have long, skinny legs.

      1. I think she is referring to yoga pants.

        I treat the narrow ones as leggings, but the boot cuts need an entirely different proportion.

        I wear a body hugging for wider yoga pants, not a loose sweater or shirt, but that goes down just past the bottom to cover what the stretchy yoga pants might reveal. The “bell” at the base needs to be balanced. Some yoga pants are thick enough to make decent pants, but you have to be careful not to look sloppy.

  10. I’m unlucky to have the apple shape body. Recently I’ve started wearing leggings and thick tights with loose tunic-length tops, but I can’t find sweaters that don’t hug my big belly. I’m 52, and look, maybe 45. Please help! I also love blazers and short (calf) boots.

  11. I love the blog and agree that a loose flowing tunic top looks amazing with leggings. This is especially true for plus sizes and the skinny women over 40 love that look too. I am a cancer survivor over 40 and love long sleeved cotton tunics with leggings are stylish and comfy for me. I buy them from Yours Elegantly online as the owner is a survivor too and donates towards cancer research.

  12. I see that someone already asked where to buy black leggings and I saw your reply, but I am having a hard time finding them! When I ask for them in stores, the salesperson shows me what she thinks I am looking for, but they always seem “not quite what I see everyone else wearing.” They have pockets or zippers that make me feel that they aren’t “legging.” Are they supposed to have feet (like a tight)? Or no feet? Can you please tell me what stores/brands I could look for? Any price point is okay. Thank you so much for your help. I LOVE the look of black leggings with longer tops/sweaters, and I would love to wear the watch, too. P.S. I am a young at heart 45-year-old who is told looks ten years younger. :) Thanks again!

    1. has friendly lightweight cotton blend leggings, ankle or Capri length for less than $40. The only thing is they run big. I weigh 165, and mediums fit me.

    2. I got a great pair of leggings at Costco! Thick like slim pants. Nice wide waistband that holds in the tummy.

  13. The “don’t wear this if you are over 40!” mentality is annoying. I also think it has more to do with your figure. If you have thick thighs or short legs, it doesn’t matter that you are 22. Not everybody and body type works with a mini.
    But, bottom line: wear it if YOU feel comfortable and like how you look.

  14. Love your website. I am 52, 5′ 10 and thin. I wear leggings with long sweaters and tall boots. But, Ive seen the look with tights or leggings with a long sweater with the shorter boot not a shoe boot, but a around ankle to mid calf boot. Would that be ok, over 40 or 50? Thank you.

    1. Hi Lisa,
      I have seen women do both looks and make it work. You are tall, so you will look great in either, lucky you!!! However, I have to admit my favorite way to wear this look is with tall boots!

  15. You can wear knee high boots or mid calf boots with skinny jeans. Since these jeans are tight on the body, they will fit well with knee high boots and you will look stylish. Also other shoes like ballets flats, loafers, oxford flats, vans , pumps can all match with skinny jeans. The choice is quite wide.

  16. 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?

  17. Love all your fashion input, however, I am having trouble finding skinny pants and leggings. Any store suggestions??

    1. 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.

    1. 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. I suggest that you retire your long blue jean skirt it will just make you look dated and frumpy.

  18. 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.

  19. 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 :)

    1. Hi Reese, I’m trying to help women put the fun back in their wardrobe, howvever I do encourage dressing “age-appropriate”. What does that mean? Well… you say that your friends say that “you look ‘teenager’y”… I say, send in a photo and I will put it up and let you know how you look and and get my readers to pipe in as well! Hope to “see” you soon!

    2. You don’t! If you like how you dress and look young, rock it! I’m going to be 30 in a few months, and I get mistaken for being in my late teens/the early twenties quite often. Don’t worry about what a blog, webpage, or any random passerby in real life says or thinks. Throw rules out the window. We live in a society that tries to curtail and contain any individuality or spunk.

  20. 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!

  21. 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.


  22. 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 rock!

    1. Hi Cindy,
      Thanks for writing in! My aim is to encourage women to have fun with fashion. “Life is too short to be frumpy!”… in other words, let’s not give up on looking chic and hip just because of a number! Glad to hear that you are already doing that and I encourage you to keep on!!
      I went to your site, and enjoyed reading your article about shopping for vintage clothes. So, from one fashionista to another, I applaud you!!

  23. 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?

    1. 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!

  24. 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.

  25. 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!!!

    1. Hi Meg,
      Ok. you got me thinking! I have not been into a Chicos for years (and I am 50)… I will give it a try! When I have tried to shop there in the past, I found everything I put on made me feel matronly.
      Thanks for calling me out on it… how can I know what a place is really like if I have not been there for a while!!!

  26. Hello dear Deborah

    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)

    1. 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 tends to be for women with fuller figures. So depending on your body type you have to be careful where you shop. Cheers, Glam Gal Deb

  27. I agree about denim mini and leggings. No one over 21 should be caught in that. 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.
    I think this look is funky in a sophisticated way and very appropriate for an adult woman.

  28. 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.

  29. 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!

  30. 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.

  31. 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?

    1. 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.

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