How To Quit Skinny Jeans

How to Quit Skinny Jeans

Bootcut Jeans Are Universally Flattering

Finally I See The Light!

“I can’t unsee it,” I said to my husband. “I know. Me neither,” he said. “I mean, you always look great, but I can’t deny that these jeans are way more flattering on you.” Not just on me, though!

Oh, this is hard. Skinny jeans. They are the thing, and have been for more than 10 years. I remember when they came on the scene my first thought was, “99% of women are not flattered by that. I will NEVER wear them.” And then, about 7 years ago, my jeans started getting more and more tapered until all I owned was skinny jeans. They are so great for wearing with riding boots, ankle boots, showing off my favorite flats, and most of what is available in stores. 

I recently came back to the knowledge that my original assessment was correct. Skinny jeans don’t flatter my figure. I take top down selfies mostly because it’s quick and easy. I can step out the door onto the flattering, shaded natural light of my deck, not worry about the background or a tripod and remote control, or anything else. I’m busy. I have about 2 minutes to get these pictures before I run out the door to take the kids to school.

I haven’t found a place with good lighting in my house to take pictures, and I feel really uncomfortable in front of the camera. I have no idea what to do with my arms and hands and legs and I seem to tilt my head a lot. Or is the camera tilted? Top down selfies eliminate all of those issues.

As a result of the super flattering top down selfie that makes everyone look thinner, I lost sight of my proportions. I am a pear, and no matter how thin or heavy I am, I am always a pear. I am wider in my hips than anywhere else in my body, which means I want to avoid drawing attention to that area. You know what draws attention to that? Skinny jeans.

They are like a giant spotlight on that part of my body. The goal for most of us is proportion and balance, no matter what our shape is. If the widest part of you is your middle or your shoulders, to be more proportionate, you need to seek balance in the rest of the body. This article refers to bootcut jeans as the jeans that flatter every body. Have you ever noticed that Jennifer Anniston, who has maybe the rockinest bod on the planet, wears bootcut jeans? If anyone in the world can get away with skinnies, it’s her, and she chooses the more balanced, flattering bootcut jean. Skinnies don’t flatter her as well because she is also a pear, but she hides it well with the proportions of her clothes. I can’t believe I just wrote that. *She’s perfect.*

Jennifer Aniston wearing bootcut jeans.
Jennifer Aniston wearing bootcut jeans.
Jennifer Aniston wearing skinny jeans.
Jennifer Aniston wearing skinny jeans.
Jennifer Aniston wearing bootcut jeans.
Jennifer Aniston wearing skinny jeans.

What I Love About Skinny Jeans

  • One length hem for all shoes 
  • Showing off all my shoes and boots and booties to their fullest glory
  • They usually arrive the perfect length for me. No tailoring required.
  • If they don’t arrive the perfect length, cuffing is cool 
  • They can be edgy or dressed up
  • Tons of varieties available
  • They come in leather and snakeskin

What I Don't Love About Skinny Jeans

  • The compression all the way down to my ankles. I start to feel claustrophobic by that much compression by about 5:00
  • I look like a pear on legs.
  • They accentuate my hips

What I Love About Bootcut Jeans

  • They are slenderizing.
  • They give an illusion of balance to my body.
  • They look more dressed up.
  • Supposedly they are the next pant trend, so I’m officially ahead of the curve.
  • They are universally flattering to all body types.
  • They are a classic style, which means they are always in style.

READ HERE: How I converted my skinny jeans to bootcut jeans with a few simple steps!

What I Don't Love About Bootcut Jeans

  • They don’t come in leather or snakeskin.
  • Even if they did come in leather or snakeskin, would I want to wear them?
  • I get full on anxiety trying to figure out the right length to hem them. I can’t commit to the cut.
  • They have to be hemmed to different lengths depending on the heel height of the shoe. I need 2-3 pairs of the same jeans to be able to wear them with different shoes.
  • What’s the point of all the awesome boots if all you see is the toe poking out? (I found these amazing boots that solve this problem).
  • They look more dressed up, and I don’t always want that.

Whether you are Cute Classic, Edgy Classic, Minimal Classic, Soft Classic or Sporty Classic, bootcut jeans work for every style, and I share how in these posts!

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My New Favorites

So this week I’ve been wearing the barely bootcut jeans I got from Express – they are my all-time favorites and can be found here. As much as I don’t want to let go of my amazing skinny jean collection (and oh, have I got some great ones!), I cannot deny that these flatter me more. This is an experiment to see how I feel. Will I abandon skinny jeans forever? Will I ignore my body shape and wear what I like? Will I wear some of both? I’ve decided to do a 30-day challenge to give myself time to adjust to something so different, because, let’s be honest, I HATE CHANGE. So, 30 days with no skinny jeans. How will I adapt my edgy style to a decidedly unedgy style of pants? I have no clue. I’ll figure it out, though.

Below you’ll see a comparison of side by side pictures of skinny and boot cut outfits.

UPDATE: After this experiment, I switched to bootcut jeans exclusively, even after losing 15 pounds, cause I’m still a pear. I talk about how to love your body type in this video when I purged my closet. My favorites are these barely bootcut jeans in dark wash and in black. You can see all the options here. You can see more of my bootcut jeans outfits here.

Black and blue camo, y’all. Maybe it’s my Southern heritage, maybe it’s my love of the outdoors, maybe it’s tough and whispers of danger, but I LOVE camo. Trouble is it always comes in the olive green color that makes me look like I have the flu. But this uber soft tee comes in my two favorite colors! I couldn’t get it in my cart fast enough! I wish they would make it in (bootcut) pants too. I’d be all over that. I chose this necklace because the shape mirrors the camo pattern and because it’s brushed silver instead of super shiny. These stabby earrings have a thin chain look dangling from them, and that is definitely a weapon. I call this my assassin look.

As for the pants, you can see in the pictures the skinnies are doing me no favors. I hate that the bootcut cover up my awesome moto boots, but what are people likely to notice more, my hips or my buckles? The skinny jeans are also edgier, which I love. The bootcut seem dressier and more reserved. I like the way the bootcut look on me, but I like the skinny jeans with the outfit. 

Jacket similar here. Tee here. Jeans here. Boots here. Necklace rose gold version here, similar silver version here, smaller version here. Lipsense 2x Purple Reign, 1x She’s Apples, Glossy gloss.

39 thoughts on “How To Quit Skinny Jeans”

  1. I am wondering if one if the reasons the bootcut is more flattering is because it lengthens your leg. I’d be interested in seeing the leather skinnies with heeled black booties that you put under the edge of your pants. I think it would give you the look of length but you can keep your edge.

    1. I’m 68 years old. Apparently I look a lot younger. I volunteer at a school and they thought I was in my forties! So I have seen every style of jean come and go and to be honest, unless you are slim with long legs, skinny jeans are a complete disaster! My husband commented the other day that if you threw a stick anywhere in this country, you’d hit a fat person and he’s right. People are so much bigger these days than when I was young. When I went on my honeymoon a size 12 pair of shorts UK was 24″ waist 36″ hips. These days a size 12 is equivalent to the old size 8. So that said we should at least embrace styles which suit a lot of people rather than wear jeans which make legs look like sausages! Wear you jeans so they skim the floor with high heels. The longer your legs, the thinner you will look. If you have fab shoes you want to show off, wear a midi skirt or pedal pushers or if you have good legs, shorts. Have straight legged jeans or skinnies to tuck into boots which will detract from the ‘sausage leg’ look.
      If we all think we have to wear skinny jeans for ever, where is fashion? Will we be stuck with one…..mostly unflattering shape of jeans for ever? Surely not. And before anyone starts complaining about me mentioning that we are all too fat now, just remember it’s only because we eat and drink too much and move too little. Fat equals unfit and early death and or health problems. But since we seem determined to make each generation fatter than the last, let’s at least try and dress to look slimmer. Skinny jeans do nothing for anyone but the slim.

  2. If you feel more comfortable in bootcut jeans than you should absolutely wear them, but other than the leather ones that are maybe too snug, I think the skinny jeans are better for you. The bootcut jeans are just as tight from the waist down to the knees as the skinny jeans are and I don’t see a big difference with that. Plus – and maybe this is the biggest thing – they just aren’t edgy enough for you. I love your style and, in my opinion, the look you had cultivated for yourself is perfection. Maybe that is part of the problem? We T4’s love to perfect, but your look is already perfect. You even mentioned recently that you have perfected your makeup. So, consider that it’s possible you are now looking for changes to make in order to keep perfecting your look. You spent so much time (years?) perfecting your look and now you’ve done it so maybe you are missing the journey. I hope you aren’t taking this negatively. I’m a girl’s girl all the way and I always want to support women. You should absolutely do whatever you want to do and whatever makes you feel best and if you want to wear bootcut jeans, then I absolutely support you in that. It just makes me kind of sad that you are changing your perfect look because you think you don’t look as good in skinny jeans. You are a beautiful and sexy woman and I think you look great in skinny jeans!

    1. Claris, thank you. I do love my style, and I’m struggling with how boring my pants are. I like to wear a lot of solids on top, and in those cases I like to mix it up with my bottoms. I started out trying to find out the most flattering length and cut of tops for me. I’ve been on a quest to figure out exactly what I love about certain things, dissect it, so I can look for those things when I shop. I’ve narrowed down a lot of the details, but some of the fit things are where I’m not sure. Anyway, what started out as a hemline for shirts turned into a rabbit hole, and now I’m wearing bootcut jeans and feeling conflicted. I don’t know if I need to give this more time and more chances to figure it out how to combine my edgy style with the dressier bootcut jeans.

      1. Keep in mind, as we perfect our look fashion AND our bodies AND our age AND our maturity as an individual, in business and our communities is ever changing. Even when we’ve lost 15 lbs. what looked good on us as 20-somethings no longer works for who we are at 35 or 40. Life is not stagnant!

      2. Would you please share a link or name of the boots from Nordstrom? Not the moto boots but the ones with the studs around the soles. My arches are incredibly high and it’s so hard to find shoes that are comfortable! I’ve been looking for a pair of booties that I can invest in that will last years. Thanks!

  3. I think you look great in both! I don’t think the boot cut makes enough difference to not be able to wear the skinny jeans you like! I know you will figure out what you want to wear. I was on my way to buy jeans this morning for a trip so I will now try on different types instead of the some kind I always wear. Thanks for opening my eyes!

    1. Thanks Connie! I’m trying to reserve judgment until the end of the 30 days, but I’m already feeling itchy.

  4. I’m with you on skinny jeans feeling claustrophobic and I hate taking them on and off. I usually get straight cut jeans because they’re a little bit wider than the skinny. I haven’t seen that style out this season but the Express barely boot cut remind me of a straight cut. Also, I’m with you on trying to figure out the appropriate place to hem them. If you figure it out, I’d love to know! As far as making them edgy, what about an edgy belt and doing a partial tuck? One last thing, have you heard of Metrostyle? They’ve got leather boot cut pant options. I’ve never ordered from them but I’m really curious now.

    1. Julie, Express skinny jeans are more like straight cut. The jean leggings are really the skinnies. The barely boot is turning out to b more like a straight cut as far as hemming. I had them at a length appropriate for a true bootcut, and that was making me unhappy. It was bunchy and sloppy feeling. Getting the hem length right will likely make me happier.

  5. You are one of the most honest people I have come across, April. You put the spotlight on issues that others run from. As far as the jeans are concerned, I learned from different experts over the years, that boot cut jeans give better balance our bodies. I would say in my opinion, that is true, if you are a certain shape. What it comes down to is how you feel, and your comfort level. I wear skinny jeans, which for me are too tight and spotlight areas I don’t particularly like. I have decided that it is time for a change, and I am going to shop for some less tight leg casings, and that is okay. This post has been very helpful and has put me on a new track, because one size does not fit all. Thank you!

    1. Diane thank you. Not everyone always appreciates my honesty, but I’m glad it’s helpful to you. I still love Express jeans.

  6. In all honesty, I don’t think the skinny jeans draw attention to your hips. If you hadn’t shared that you have a pear shape, I wouldn’t have guessed it, but still don’t really see it. When I see your outfits with skinny pants, all I see is how amazing you look. I think as women, we fall into the trap of feeling more self-conscious about our bodies than we need to. So, even though I think you look amazing wearing both types of pants, (though edgier with the skinnies), maybe something to consider is that wearing your skinnies with jackets adds a nice balance. When you aren’t wearing a jacket, your boatneck tees also give the illusion that your shoulders are wider and you could achieve balance that way instead of with bootcut jeans.

    1. Thanks Ruth. I’ve been having some of those same thoughts. Am I seeking a more flattering silhouette, or unnecessarily shaming my body shape and picking myself apart? I enjoy looking my best. It makes me feel my best. I’m more aware of the details you mentioned, like boatneck tops. I do have narrow shoulders, and that helps widen that part. It may be a matter of learning to nail the details up top when I want to wear skinny jeans.

  7. So I’ve been thinking about my first comment and I don’t feel good about it. I think I gave some opinions that you didn’t solicit and I apologize. I was going to take it down, but I can’t figure out how to do that. This wasn’t a FB post with you asking people for their opinions and while I meant it all as a compliment, I’m not sure it came across that way. You are a smart woman with impeccable taste and you will quickly figure it out on your own. If I could redo that comment I would simply say: Wear whatever you want to wear, but I think you look great in skinny jeans!

    1. Claris, no apology needed. Your comment was thoughtful, helpful, and meant with positive intentions, and I appreciated it. This is meant to be a discussion. I’m still thinking about it and working through it, and I am interested in other perspectives. I love my personal style and feel 100% content in it. If I can incorporate some details to make that look even more flattering, then I would love to do that. At this point I’m in a serious adjustment phase. How can I get the best of both?

  8. In reference to the Jennifer Aniston pictures, bootcuts definitely make her look taller! If I remember correctly, she is a Type 2, and she is totally rocking the comfy layers and many of the colors! It’s pretty cool when you see someone who may not be aware of DYT dress according to their type.

    I think the top I am wearing, how much stretch is in the jeans, and color make all the difference in skinny jeans. I don’t like it when my pants feel glued onto my legs. I like I bit of weight to the fabric—I supposed that is very Type 4. I don’t like to wear light colored skinnies at all because I feel it draws too much attention to my hips. No matter what color my skinny jeans are, I like to have my hips somewhat covered which helps create balance since tunics skim with widest part of me. You might not have to abandon them if you go for a longer top! Especially since you have so many cool jeans.

    I feel like leather or snakeskin bootcuts would be super 1990s…which is good if that’s what you’re going for, but otherwise might be a bit dated.

    Whatever feels more comfortable on that particular day is probably perfect because you will behave comfortably instead of constantly adjusting your clothes.

    1. Thanks Cassandra. I agree about the boot cut leather or snakeskin. It feels…weird. I’m still making up my mind, but for now I think there is a place for both in my wardrobe, and your suggestion of different length tops for different pants is a possibility. I’ll have to try it out.

  9. I was on the Express website tonight and thought of you. You probably saw this but did you see the frayed skyscraper jeans at Express? They’ve got an opening for your boots and the knees are torn. They’re highwaisted and I’m not sure how you feel about that.

    I just wanted you to know that I love your style. I also think it’s cool that you’re exploring other options for your style. I love that you don’t seem to be afraid to try something. Love your post!

    1. Julie thank you so much! I appreciate that. I’m always open to refining my style. I love to perfect. 🙂

      I haven’t seen those jeans, but I’ll look! High waisted are usually a huge no no for me because I’m so short waisted. High waisted jeans could double as a romper for me. It is usually super uncomfortable. Maybe I can make the barely bootcuts look like those.

  10. I recently bought some jeans from Express during the sale (thanks for the tip, April). I bought my first pair of distressed jeans (skinnies) and, surprisingly, I really like them. I would have never, in a million years bought a distressed pair until I saw you in them. Now I’m in the T3 camp, I wanted to get away from my usual perfect and crisp purchases. Also, I did buy a pair of boot cut. As a shorty, but with an apple shape, these are to elongate. Look pretty good, but I agree, not really edgy on their own. You are still my idol, April. You look fabulous in everything! Just don’t wear those God-awful crop flair jeans with the torn edges. Ugh! It looks like something Oliver Twist.

    1. Rebecca, thank you!! I’m so glad you branched out and tried something new, and even happier that it worked for you!!

      I was long and scrawny growing up, and there were no size 0 or 00 or even 1 or 3. I always had to choose between jeans that were long enough or jeans that didn’t fall down without a belt. I’m super sensitive about jeans that aren’t long enough. Those kind of jeans got me teased as a kid. I will never wear those.

  11. I don’t have any comments on the jeans, though I personally like bootcuts better because I’m short. My burning question is how you got used to the necklaces. As a T4, I’m still wanted to rip them off, because, too much movement.

    1. Serena, it’s about finding the right necklaces for me. They have to be lightweight and not move around. If I don’t feel them and notice them, they don’t bother me. I do have some more substantial jewelry that doesn’t bother me on certain days. It also makes a difference which earrings I’m wearing. I tend to go statement necklace and stud earrings.

  12. Interesting post.
    To note, Jennifer has what we (my Greek friends and I), call HHD or Hellenic Hip Disorder. Tongue in cheek, it’s our reference to the fact that many girls of Greek descent have more hip than others.
    And yes, bootcuts are more flattering on that shape in general. Jennifer always wears them long with high heeled boots, to create the illusion of longer legs.
    You look fabulous in both skinny, slim fit and bootcut.
    Have you challenged yourself to work out if your hips are proportional to your height, rather than your waist or bust measurements. Many girls think they are hippy, but it’s actually not that at all.
    Now me, I love all cuts of jeans. I’m 5’8" so a pair of nicely heeled boots puts me up at 6′ or well over. Yes they slim me down. They look better in a strong mid royal denim colour than
    Dark or they need to be in total black.
    Skinniest started appearing over 10 years ago on the uni students.
    The trend to go back to flares failed miserably a few years back. Too much excess? Maybe so. Too much extra room when packing? Who knows. What I haven’t seen in my world travels has been more people wearing traditional bootcuts.
    I always have them in my wardrobe. Can’t wear my cowboy boots without them. I have slim bootcuts, bootcuts and flared bootcuts.
    Here’s hoping they appear in more leather, snakeskin or edges materials.

    1. Belinda what an insightful comment! Thanks. I followed a formula where I measured my shoulders, bust, waist, natural waist, and hips. I know I’m fuller in the hips than up top.

      I agree the jump to flare a few years ago was too extreme and too soon, and I think the bootcut trend will pick up and gain traction. For me, the key is how to make them edgy. They can feel way to dressy for me since a lot of what I tend to wear above the waist is more classic. It can feel too classic. Currently I’m wearing some skinny, some straight and some bootcut. If you see them in leather, snake skin or something edgier, holla!

  13. I LOVE your style. I, too, prefer to dress a little edgy, but with my (ahem) substantial curves on the lower half, skinny jeans just do not look good on me, but I feel bootcut jeans look too "put together". Oh, the dilemma. I am so happy to have come across your article and am curious as to how you are doing in your quest for the perfect amount of edge in bootcut jeans. Also, I see several people refer to T2 or T4 in the comments, and I’m not sure what that means. Probably something that is the case where if it affected me I would know what it meant, lol.

    1. Hope welcome and thank you! I’ve stayed true to bootcut jeans, and I can’t go back to skinnies. I’ve been incorporating more edginess from the waist up with jewelry and other details. I’m trying to keep the focus on my upper half.

      You can read more about the references to T2 and T4 here.

      I also did a series of closet purge videos and talked more about jeans here:

    1. Thank you. I appreciate that. Honestly, overthinking is what I do, and I’m constantly trying to perfect and improve everything! Dressing for my body type has been a really interesting journey. Now that I know the rules I know which ones to break and which ones to follow. This is one that makes me look and feel better, so I stick to it. Other pear shape tykes I follow selectively, and still others I disregard entirely. Not everyone has to do this, but I’m sharing my experience for those who are interested in the topic.

  14. Love this post. Anyone concerned about their dark wash bootcut jeans looking too dressy just needs to also have a pair of lighter wash bootcuts for a more casual look. I think everyone looks better in bootcuts. I suppose, technically, I could wear the skinnies, since I’m a slender hourglass shape, but I think they’re one of many styles that are best for the under-20 crowd. The length thing for different heel heights IS a thing, but I’ve pretty much solved it by always buying shoes that will be worn with them in a pretty tight range of 1 1/2 to 2 1/4 inches. I’ll be back later to check out more of your blog.

  15. And WHY do pears wear jeans with sequins and sparkles on the butts? It’s just calling more attention to it!

  16. To be honest, the skinnies, in this instance are more flattering on you than the bootcut. I haven’t seen a comparison in other aspects other than this one as I am skimming but this particular one, the skinnies win!

  17. I’ve always thought those with no shape (no waist or hips) are the only ones who should be allowed to wear skinny jeans. Anyone else (they do try), well it’s just not flattering, the shape or style.

  18. I can’t wear a skinny jean. I’ve know it for years. I’m not heavy. I’m 5’7 123 lbs. I just have a thicker leg and a short waist. I look like I’m wearing a skinny if I can find a “slim” fit. But skinny no way. I can’t even get my size 10 foot in the tiny bottom of a skinny pant. AND I AGREE 80% of women look terrible in them. 🤦‍♀️

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