How to Wear Skinny Jeans

I love skinny jeans. I didn’t at first, but once I gave them a try, I haven’t looked back. I wear skinny jeans with flip flops, with ballet flats, and in the winter I tuck them into my boots.

I know what you’re gonna say. A lot of people think they can’t wear skinny jeans, but it’s really all about proportion. So I figured it was time to write a post about how to wear skinny jeans.

How to Wear Skinny Jeans

 Here are a few general rules of thumb about how to wear skinny jeans, and when to break them.

How to Wear Skinny Jeans

1. Wear skinny jeans and jeggings with a voluminous top, fitted jacket, or a long cardigan.

When I first wrote this post, this was definitely the rule. But nowadays you will see skinny jeans worn with all sorts of tops. If you are new to the trend, you might feel more comfortable wearing them with a longer top, but as you get more accustomed to wearing them, try them with various styles on top. It really depends on your body proportions and comfort level. Here are a few sample outfits with skinny jeans.

color blocking pink and red

white jeans after labor day

TIP:  If you’re shy about wearing a skinny jean or jegging, opt for a straight leg jean.  They give you the slimmer silhouette without the dreaded ice cream cone effect. This is a great way to break into the trend without going whole-hog. Although that’s probably not the best choice of expression. *giggle*

2. Wear skinny jeans with boots.

Virtually everyone agrees that skinny jeans look great tucked into boots. The added bulk of the boot on the bottom provides balance so that even girls with junk in the trunk can pull off the skinny jean with boots. It took me a while to find boots that worked for me. I am rather, er, top heavy, with wide hips and skinny legs, so I feel best in boots that are a little more bulky.

But what do you do when it’s too warm to wear boots?

I read one article that said to always wear skinnies with ballet flats or boots and to leave the heels for the super models. But the same night that I read this article, I was with a friend who can pull off skinny jeans with heels like nobody’s business. She was wearing them with a pair of high-heeled slides and looked adorable. Her secret? She’s about 5’2″ and is very well proportioned. She almost always wears heels because she wants the added height, and they actually help her achieve the proper proportion with the skinny jeans.

If you’re a plus sized gal, don’t think you can’t wear skinny jeans. Try them. You might be surprised. My best advice is to wear them with a chunkier shoe to balance out your frame. And you probably want to wear them with a more voluminous top, but this really depends on your proportions. Perhaps a fitted blazer on top will work best for you. Consider the looks below.

Plus Sized Red Skinny Jeans

Plus Sized Skinny Jeans

The next day I saw another article that said to only wear skinny jeans with heels, that wearing them with flats makes one look stumpy. But I take umbrage with that blanket statement. With my giraffe legs, I look much better when I pair skinny jeans with flats.

So what’s a girl to do?

It really depends on your body type.

If you’re short, or you have short legs for your frame, heels may work just fine. Since I’m leggy, I’m much more comfortable wearing my skinny jeans with flats or tucked into knee-high boots. I generally save my heels for my boot cut jeans. That said, it’s a woman’s prerogative to change her mind, and if I suddenly decide to start wearing skinny jeans with heels, I will plead the fifth.

UPDATE: My eye has adjusted, and I have, in fact, been known to wear skinny jeans with high-heeled pumps on certain fancy occasions.

I think when it comes to heels vs. flats, you have to ask yourself two questions: What do I feel most comfortable in? and What looks best on ME?  (Not the super model in the magazine or your 21-year-old neighbor next door.)

3. Go for a dark wash. Fit is key, but dark colors generally are more slimming than light colors. Again, all these rules fly out the window if you are young and thin and perfectly proportioned. (Lucky you!  Of course, we all kind of hate you.) But for most of us, a skinny jean will look best in a dark, consistent wash.

Fun Girls Night Out Outfit

4. Ultimately, wear what you like and feel good in. If that’s a boot-cut jean, then so be it. Give yourself permission to opt out of any trend that doesn’t work for you. You can be stylish and modern without being trendy. In fact, I highly recommend it.

How about you? Are skinny jeans a do or a don’t? If they’re a do, how do you make them work for you?



  1. pixielation says

    I have a few skinny jeans, and I tend to wear them with tunics and boots in winter, and ballet flats in summer. I do have heels – they live in boxes in the spare room and still think it’s the 90’s because shoes have no idea about the passage of time.

    I think if you look in the mirror and it looks good, wear it. You do have to be on the lighter side of average to make skinny jeans looks good though. There is no point wearing them if they unkindly point out all the lumps and bumps that make you you. A looser fit would make you look fitter in that case.

    • Jo-Lynne says

      “they live in boxes in the spare room and still think it’s the 90′s because shoes have no idea about the passage of time.”

      Hahaha. :-)

  2. says

    I dunno, you know I still say I can’t do it. lol. I love the look on most ppl but I have such hips… Boot Cut is just so the way to go for me. I’m crying uncle and passing on this trend… should have said that for shoulder pads but I’m older and wiser now:)

    • Jo-Lynne says

      LOL about shoulder pads. I have broad, square shoulders and a short neck. WHY didn’t someone tell me how foolish I looked??

      I do hear ya on the hips. I have em too. With skinny legs and hips, I was self conscious about the skinny jeans. My trick? The straight leg. The ones I wear are technically straight leg, so they are not skin tight, but I get the slimmer look. I do love bootcut jeans with heels, but with flats, I am really into the skinny/straight styles. And nothing tucks into boots except skinnies.

      All that to say, it’s worth a try, but ultimately you have to wear what you’re comfortable in. And you look so cute in skirts, you probably don’t wear jeans as much as I do.

  3. says

    Hmmm. Well, first I’m too old to wear those young trends. I REALLY don’t want to look like an older woman trying to be young — gag, I hate that look of insecurity. I’m 47.
    Second, I’m too fat, in my opinion. Is this the thing you were graciously trying to skirt around in your post? Skinny jeans are for skinny people, right? I really, really detest seeing fat teens in public who have poured themselves into jeans 2 sizes too small, and they are overflowing the top. Maybe it would be good to just openly address this. Do you have attractive pics of larger women in skinny jeans? How big is too big?

    All that said, I really love big, roomy shirts and sweaters. :)

    • Jo-Lynne says

      You bring up some great points. Obviously, stick-thin people have more liberty when it comes to wearing different trends. BUT. I don’t think that heavy girls can’t wear skinny jeans. AND. Not all thinner/average girls can either.

      For example, Whitney, above, I know her in real life. She’s an average/thin girl but feels like skinny jeans aren’t for her b/c she has hips.

      On the other hand, I have seen some heavy girls really pull off the skinny jeans, which is why I included photos of plus-sized models in the last picture with the different jeans.

      The key is wearing the right size. The teens (or anyone, really) pouring themselves into clothes that are too small is a shame, really. They could look great in the same clothes if they’d go up a size or two.

      When I gain weight, even 5 lbs, it really shows in my clothes, and I went out last spring and bought a few new pair of pants in a size up so I didn’t look like I was squeezing myself into a sausage casing. In other words, we always look thinner when our clothes fit properly.

      So, I don’t know what size is too big, but you mention big, roomy shirts — they work well over slimmer pants. So perhaps a straight leg pant would read like a skinny jean (I wear straight-leg styles and consider them skinnies) under a roomy top.

      Again, a lot of it depends on the proportion of a woman’s body. Some carry their weight on top, some on bottom, and some all over. If you carry it on top, a skinny jean will only call attention to that, so it may not be the best look. If you are more evenly proportioned, it can work.

      I think age is always a good thing to keep in mind. At some point, the trendiest looks are just not appropriate for most women, although there are always the exceptions to that rule too.

      • says

        Yeah, I noticed that one of the models does look larger. I never know in pics like that, if “larger” is a size 14, or a 20, y’know?

        I do have long legs, and I carry my weight pretty evenly. The only part I really hate is my belly, after 4 kids. But, like you said, the roomy, long top would cover that up. I like that. For some reason, I’ve always considered the skinny jeans to be, um, a little indecent. Sorry to say! But like you, just a straight cut is a good choice. Thanks for the advice, and I’ll try to buy IN MY SIZE :)

        • Jo-Lynne says

          Yes, I know, the whole “plus sized model” thing is such a crock. I do have a friend who is a size 14 and she bought jeggings when I was with her, and with a longer top, she looked really cute.

      • says

        Seriously?!?! You say these models are “plus-size”??? That really does a disservice to those of us mamas who really are plus-size. I have recently lost 65 pounds and I am STILL more plus-size than any of those models.

        :( :( :(

        • says

          I’ve updated this post since these comments were made. No, there are no plus sized models in those photos. It is VERY hard to find photos online of plus sized women wearing clothes, and when I do they still aren’t very realistic. I do remember the photo that was being discussed in this post. I’ll see if I can find it.

        • says

          Okay, I have updated the post again — there are two new outfits with plus sized clothing. I tend to write from my personal POV so I often forget to include photos of other sizes in my fashion posts. This is something I will work on going forward! Thanks for your comment. :-)

    • Bes Van Bael says

      I’m 5’8″ and between 146 – 150 lbs. And I need to say that I am 53 years young. I never let age dictate what I can or cannot wear. Granted, you won’t catch me in a crop top unless I can flatten my tummy but… skinny jeans are fantastic. I too have that stinking midsection that I want to get rid of but, the skinnies are great with a nice tunic, long sweater, etc. I love wearing them with knee high boots, combat boots, etc. You can dress them up or down…all depends on the top and your shoe. I also love leggings in the winter with tall boots and a long cardigan. There is so much out there to try. Having a 14 year old daughter, I find myself looking at the outfits on Polyvore and Pinterest. Good ideas on putting an outfit together and don’t forget to accessorize! A oversized handbag adds that pop of color. Let your imagination run. Age is just a number…it all depends on how you feel inside. I also have a 17 year old son. I love to express myself in clothing and I do have multiple ear piercings. Just go for it!

  4. Beth says

    I hate my thighs, and haven’t needed new jeans since the skinny jean trend started since I can’t wear jeans to work so I haven’t even tried them on. I am in the market for new black boots this fall though so I may just have to at least see what I think of them with boots when I find a pair.

  5. says

    I have to put my 2 cents in, being chubby myself and EVEN OLDER than Mary Kathryn. :-) I love the skinny jeans! But haven’t found an affordable pair that rides high enough on my waist. I got a pair of jeggings, though! (Is that word dumb or cute??)

    Jo-Lynne is right on – you have to wear the right size no matter what your size. She’s also right that proportion is key. If you carry your weight on top and have thin legs, this is not the look for you. If you have average, or even heavy legs – which I do – I think they can help the proportions.

    I have to balance out what I wear on top – something not too voluminous that will make me look like a grape, but not too fitted that shows my muffin top. I am very conscious about dressing too young so I try not to wear anything too trendy or young on top – esp anything with bows, ruffles or puffy sleeves, which I dislike anyway. I try to stay subdued in color and/or style. I just ordered an interesting tunic-length white blouse. Can’t wait to get it.

    I can hardly wait for fall so I can wear my long cardis with my various leggings.

    • Jo-Lynne says

      Yes, you can totally pull off the leggings and skinny jeans. It’s a great look on you, and you always look age appropriate.

      And I hear ya on the low-rise — the Miraclebody Jeans I’m giving away on Chic Critique are really high-waisted. They have skinnies and jeggings. Also, Not My Daughters Jeans are higher waisted, I think. But of course, both are $$$.

    • Patti says

      Try Joe Fresh (Canadian brand but probably available over the internet). The price was amazing, the skinny fit was generous enough for this 49 year old size 10, came in cords or jeans in many colours. $19.99. Even if you wear them one season you get your money’s worth then pass them on to your kids 😉

  6. says

    My Latina hips + skinny jeans = recipe for disaster. I’m skipping this trend and sticking to boot-cut jeans. Kim Kardashian can pull off skinny jeans though, so I guess it can work for some ladies with large, ummm, derrieres.

  7. says

    I grabbed a few pair of skinny jeans and a pair of jeggings last fall. the jeggings are super dark wash and I only wear them tucked into tall boots and with a longer top, as well.
    My skinnies I will do a little more with, sometimes tucked in, sometimes with a flat and sometimes with converse sneakers.
    I definitely go with the longer tops, and maybe a open style cardigan or boyfriend jacket.
    I’m 47 too, and try to be sure whatever tops I am wearing also seem age-appropriate, but I will wear a patterned T under the BF jacket & the converse for a fun casual look like going to my DS baseball game 9. I think the whole look you put together has to be what makes you feel good (and fits 😉 ).

  8. says

    I had sworn off the skinny jeans thing, thinking that with my pear shape only boot cuts would ever work for me…that is until you girls convinced me to try on the jeggings at the LOFT style event. OH so comfy! And I wear boots a lot here in TX so I’d like to be able to tuck my jeans into them sometimes. The key does appear to be what top you wear with them. Now I’m anxiously awaiting non heat advisory days here so I can wear the jeggings. Also I now need a LOT more boots :)

    I did a Fashion Friday post as well about a kids clothing swap service :)

    • says

      Oh, and I’m SO glad you included those jeans from Torrid with a plus size model in the photo. Curvy girls need cute clothes too!!

      Also, I picked up several boyfriend blazers recently and I’m thinking as long as I don’t take them off, they’ll look great with a tank top and my jeggings (or skinny jeans which I have yet to buy).

  9. Kristin says

    I have to agree with Mainline Mom – as a fellow pear-shaped lady I swore off skinny jeans for the longest time. Then I realized it was absolutely ALL about proportion! I love wearing slouchy boots and the new foldover ankle style boots with my skinny jeans and blazers are my new best friends :) Still wavering on the jeggings trend…baby steps.

  10. Barb @ My Daily Round says

    I have absolutely nothing to contribute about the skinny jeans since I haven’t tried them, and I stick to my Gap casual fit when I can find them in thrift shops. But…do these jeans work if one has a bit of a belly after having five kids? Mind you, I look okay elsewhere, if you don’t look at the thighs, but I have a small poof.

    I do agree that fit is incredibly important. Funny, I learned that watching What Not to Wear. I took my daughter with me when I went bra shopping Wednesday and she wanted to know why I was trying on so many bras. I explained how important it is for even underwear to fit correctly. We just feel better about ourselves when our clothes fit correctly.

    • Jo-Lynne says

      The best thing, if you have a tummy, is the Miraclebody jeans. No lie. They have a nice, high waist that keeps everything tucked in where it belongs.

      I’ve had 3 kids, and even though I’m at my ideal weight (well, not MY ideal, but the doctor’s ideal, lol) I still have that nasty jelly belly. I HATE IT. I have decided that I either have to work out with a trainer or just get used to shapewear. I have multiple pieces of shapewear, and I use them a lot. It’s the only way to wear low rise jeans and not look like a fashion victim. :-(

  11. says

    Ok, I will *NEVER* be on board with jeggings. Never. I don’t care if God comes down from heaven and tells me He made them just for me, they aren’t. ever. happening. here.

  12. says

    I’m only 5′ 2″ and have really short legs, but I found skinny jeans at banana republic that fit well. I got them to go with the furry coach boots I got for Christmas. Just because they are skinny jeans, that doesn’t mean they have to be tight. Mine fit the same in the waist and hips as my straight legs and boot cuts. Since my baby is due at the end of November though, they’ll be taking a break this winter!

  13. Jen says

    LOL, I love me a good trend but this is one that I ran SCREAMING from. Hell to the no! I don’t like this look, even on Kate Moss… but if I weren’t so darn fat and jealous, I’d probably try it out:)

  14. says

    I’m 5’2″ and I got some great jeans from Banana Republic in their petite department. They were on sale for $20 each, and I swear, they’re awesome. I would have bought more of them if they had them but they only had two pairs in my size.

  15. says

    I am 5’3″ (and half — I must include the half!!) with short legs and I just don’t think I can pull them off without heels. And since I am running after a toddler and hauling around an infant, I live in ballet flats. Maybe I will try them in the fall with my boots, no heel, but could work!

  16. says

    Being not only overweight but extremely hip-py (and, well, pregnant), I can’t even imagine trying a pair of skinny jeans. I feel like I need the volume on the bottom to balance out my hips. Love trouser jeans.

    But if you can make it work, go for it! Love them tucked into boots.

  17. Kelly says

    Like you, it took me a while to get excited about skinny jeans and sometimes i just don’t know how to wear them. Thanks for sharing these tips!

  18. Lisa Kelsch says

    I wear skinny jeans w/ boots when it rains, or all winter as the case may be. Its warm and your feet stay dry, and unlike sandals, you do not slide on a wet tile floor. I pair them with all sorts of tops and hoodies…and feel comfy and warm. In the summer they’re paired with ballet flats and sandals. Its really all about how you feel wearing them…if you have the confidence to dare to pull off skinny jeans, then by all means that’s the only fashion accessory you really need. :o) BTW the trend of skinny jeans and UGG boots is HUGE here! <3

  19. Barb says

    Great article. Ive tried alot of skinny jeans and the know the brands that fit best. I do like them and wear them with boots tucked in to flats. There are variations to skinny jeans from legging type to tight but slightly looser ankles that I prefer. My husband likes me to them with high heel mules or slides,kind of creates a cialis moment.

  20. nayla says

    hi..Jo… i never have jegging,even i want to have 1 pair though. this day i was in store and tried 1 pair of jeggin.. i love the color,but somehow didn’t feel comforable when wearing it. besides i have these big size calves which makes my shiloutte looks so funny. does it mean i cant wearing it?

  21. Liisa says

    So I’m 6 foot with a 28 inch waste, 38 inch hips and I want so badly to look great in this skinny jean trend. I’ve been trying my one and only cheapo (Ross) pair with heels and ballet flats and I’m still not convinced it’s flattering. I definitely like the darker washes or even black. Is there a point on the ankle that you think they should line up with?

    • Liisa says

      could I possibly message you a silly in the mirror photo for a woman’s opinion? My fiancee does not understand female trends in the slightest :)

    • says

      I think a lot of it depends on proportion. Like, are you leggy? do you carry your weight in your hips or upper body… all of those are factors. My instinct is to say, stick with flats since you’re tall.

      I personally prefer the right below the ankle length — not ankle-length or cropped, but the kind that hit right before they buckle on your foot. Like in my most recent post, Daily Mom Style – the green ones. I love that length. It is easy to wear, it doesn’t chop off your leg, but you don’t have to worry about your heel height or anything.

  22. Amber says

    Ok, normally I don’t post on blogs but I think the topic is hilarious and informative! I am a skinny young woman. 20 years old and a size 2. I am “above average” 5’8″ height and described as “willowy” or *sigh* “gangly” in figure. I CAN”T WEAR SKINNY JEANS!!! though, I would love to! So, reading several other comments, I’ve seen many “larger” girls pull of this trend very gracefully and I think that they should go for it (because they can). As for me, I’m going to try some boots and pair them with with some skinnies or a straight– because I am a loyal boot-legger.
    I hope this works, because according to nearly every fashion article I SHOULD be able to pull off skinny jeans! Maybe it’s my hips:)haha

  23. Toni says

    I can relate to your friend that wear her skinny jeans with heels .I do wear mine with flats my favorites is to wear them with high heel slides or mules.I love the look

  24. Ash says

    I’m 5ft 5″; my body measurements are 32-25-35 but I’ve recently been trying to figure out how to dress my body. I’ve heard that I have a pear shape, any tips?

    • says

      Hi Ash. I’m the opposite, I’m kinda top heavy, but the general rule of thumb is to try to create the illusion of balanced proportions, so perhaps wearing something a top that balances creates volume on top will help balance out the pear shape. I find taking photos of myself really helps me get a better perspective on how I look in various outfits. Good luck!

  25. Nann says

    Oh, thank you fellow Jesus girl. This frumpyish 40-something never quite had the fashion sense most girls seem to. I lost 63 lbs and ventured out to get my very first pair of skinny jeans. Used Google voice to ask how to wear them and BAM. Here you are!

  26. sarah says

    I wear skinny jeans alllll the time with all types of tops. One of my favorite looks though is skinnies with a chiffon blouse and riding boots. I personally don’t like jeans with ballet flats because my feet are size 9 :O and I think it looks weird. I wear them with boots most of the time and sometimes wedges but I’m 5’9″ so I don’t really need the height unless I’m at a volleyball event where everyone is tall haha

  27. Mai says

    Hi love your blog! Got a question, I’m tempted to try on skinny jeans never got the courage to though! I’m busty with long skinny legs and narrow hips ; should or should not?

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