I’m so excited about today’s post — it’s been in the works for a few months now!
I started testing out straight leg jeans in the summer, and after many try-ons and returns, I’m excited to share with you the best of what I found. All four of them are under $90 and pass my comfort test.
Keep reading because in this post I’m sharing:
- my “aha” moment when it comes to finding comfortable high rise jeans
- how to stretch your non-stretch jeans to make them more comfy
- my tips for cutting the hems of your jeans
- how to keep your ankles warm and draft-free when wearing straight or wide leg jeans
Let’s jump in!
And if you see something you like, you can shop it and support Unfancy at the same time by using the affiliate links in this post.
1 | Medium Light Wash + Stretchy!
I’d almost abandoned high rise jeans earlier this year because they just weren’t comfortable around my stomach, but I had an “Aha!” moment when I tried on these lovely, stretchy jeans:
For me, the higher the rise, the more comfortable the jeans. I know, it sounds like it shouldn’t work. I thought I needed lower rise jeans for comfort, not higher. But the key is to go above the stomach, don’t cut across it. For me personally, if a pair hits above my belly button, then it doesn’t constrict my stomach near as much as it would if it were a couple inches lower. Makes all the difference.
Of course, we all have different bodies and this will vary from person to person. But try out a few different rises and find what works for you. It’s nice to know that not all jeans labeled “high rise” will feel the same.
As far as pairing straight leg jeans with shoes, I like going with a fitted sock bootie. These weatherproof, suede booties are a dream. They are an investment, but the heel is low, the angle of the heel is just right, the shaft is tall to keep out drafts, and there’s cushioning in the footbed (plus they are 40% off right now).
Sweater by HM (under $20) | similar
Necklace gifted by Edge of Ember
Jeans by TopShop (on sale, $45) | Fit note: Wearing size 25. Consider sizing down one. I cut the hems myself.
Booties by Aquatalia (on sale, 40% off)
• • •
2 | Light Wash + No Stretch
We’re having our first freeze right now and I’m so happy that I can finally wear my big ol’ vintage coat and my favorite soft sweater (Madewell brought it back this year, yay!).
Onto the denim, these jeans are not stretchy. But I always like having at least one good pair of non-stretch jeans in the rotation.
Plus, I tried something new with this pair! I stretched them myself! Meaning, while my jeans were damp from the wash, I buttoned up the fly, found a household item that would just barely fit inside the waistband of my jeans (ended up using a dish drying rack, yep) and let them air dry like that, with the waistband stretched over the dish drying rack.
And it worked! It stretched out the waistband a good inch or two. And even though they fit before, they are so much more comfortable now, especially when sitting.
A few words before you jump in:
- It’s easy to get overambitious and stretch your jeans too much to the point of ruining them. Start small by letting them stretch for just an hour or two, instead of waiting for them to air dry completely.
- Stretching the waistband probably isn’t a good idea if you tend to get a gap in the back of your jeans, because this will exaggerate that. But consider which parts of your jeans feel constricting (hip area, crotch, thigh, etc) and try stretching there.
- When you’re trying to fit whatever household object you choose into your jeans, don’t rely too much on the belt loops for grip — they can easily rip off.
- And finally, as with all 100% cotton, non-stretch jeans — always wash them on cold and never put them in the dryer. Otherwise they’ll shrink up and lose all that good stretching/breaking in you’ve done.
Sweater by Madewell | similar (conscious) | similar (conscious)
Necklace gifted by Edge of Ember
Coat (vintage from Shop Stressed) | similar | similar in teddy faux fur (under $90) | similar in rich brown | similar in brown plaid
Jeans by & Other Stories (under $90) | Fit note: Wearing size 26, I cut the hems myself
Boots by By Far (conscious) | similar (conscious, on sale, under $130) | similar without laces (conscious) | similar (under $70)
• • •
3 | Dusty Black + Stretchy!
These jeans are a dusty black — emphasis on dusty. They lean heavily towards brown-grey and to be honest I wasn’t sure about them when they came out of the box.
But all that changed the moment I put them on — these washed black jeans are so delightfully comfortable, they win most comfortable jeans of this post. I think of them as my pasta eating jeans. :)
I paired them with these black booties to highlight the contrast in tone. While these are one of my most versatile pairs of booties (they look great with dresses, jeans, anything), the heel is slightly higher than I like to wear. Fine, but not comfortable for a whole day of walking. So I linked to a couple of other options below that have a lower heel, including the black version of the brown boots I’m wearing in this post, which are comfortable beyond words.
I’ve been cutting the hems off my jeans a lot this year because I like the look of a raw hem over ankle booties. Here are a few of my tips:
- Make sure you’ve washed your jeans at least once to get any shrinkage out of the way.
- Get in your closet, find a pair of old jeans that are the length you want, and measure the inseam (from the crotch to the hem). Now transfer those measurements to the new jeans. Use masking tape or painters tape to mark off a straight line, and cut!
- To cut, use a pair of sewing scissors like this pair (though honestly, I just use this pair that I already had)
- Err on the side of cutting off less (because you can always do a second round if they are still a little too long)
- Once they feel right, put them in the dryer for a few minutes to fray up the hems, keeping in mind that the stretchier the jean, the less natural fraying it’ll have
Sweater by Madewell | similar (conscious) | similar (conscious)
Jeans by Everlane (under $80, conscious) | Fit note: Wearing size 26, I cut the hems myself
Boots by Free People | similar with lower heel (on sale, 40% off) | similar with lower heel
• • •
4 | Faded Black + Stretchy!
Whew I did not intend for this post to get so long! Turns out I like sharing all the little details with you too much. How about if I keep this last one brief? :)
These jeans are a bit stiffer than the dusty black pair before it. They still have a good bit of stretch to ’em, but you can see the fabric looks more structural, like raw denim, which I really like.
I like to pair a fitted sock bootie with straight jeans. That contrast between the wider hem and the skinny boot shaft — I love it!
These weatherproof, suede booties in particular have a taller shaft than most ankle booties, meaning they keep those chilly drafts out. To combat drafts even further, I wear merino wool knee socks. Two simple steps and I’ve got warm ankles all winter long, even with my cropped pants.
Sweater by HM (under $20)
Jeans by TopShop (under $75) | Fit note: Wearing size 25. Consider sizing down one.
Booties by Aquatalia (on sale, 40% off)
• • •
And there you have it!
So tell me, are you into straight leg jeans? Do you prefer stretchy or non-stretch? Have you ever cut the hems of your jeans? How did it work out for you? Got any other tips for keeping your ankles warm in the winter? Share away!
Love this!! I love straight jeans and I love knitted sweaters and I love ankle boots. I’m considering cutting the hems of a pair of jeans, but will it work if I don’t have a dryer to fray the hems?
PS. I keep my ankles warm with woolen socks and if it’s really cold outside I wear cut-off tights under my jeans.
Good call on the cutoff tights! :) And I think cutting your jeans will still work well without a dryer. Try rubbing the hems together for a bit — you should be able to achieve the same results.
Or use a fork by rubbing across/ and down from cut to fray!
Try taking a straight pen and pulling out sections from the hem.
My AHA moment came in 1974, when high-rise pants first appeared in the stores. Before then, all we had were hip-huggers. For the first time, a pair of pants looked good on me and I’ve worn nothing but high-rise ever since. My waist is much smaller than my hips, so the most important criteria is that the pants don’t gap at the back of the waist.
I remember driving over our Levi’s to break them in.
Do you have any tips for finding high waisted jeans that don’t gap at the back? I end up buying low waisted jeans to avoid the back gap.
Sarah Winton says
I love highwaist jeans. They hold in a poochy stomach so well!
Andrea H says
Killing it – as always – with your styling! Love all of these pairings. I especially a sucker for jeans with brass rivets.
Aw friend! Thanks for taking the time to read my posts — means so much. :)
Davinia Cavaney says
Thank you for this post! I’m trying to build up my high waist jean collection! My size 27 in the other stories jeans has just sold out but managed to snap up a size 26 so let’s hope your right and I can stretch them whilst wet ?
I had good luck stretching mine, so here’s hoping! You could even try several stretching sessions if you don’t get enough the first time. And make sure to always wash them on cold and never put them in the dryer once they are stretched. :)
Loving your efforts to take a pair of fresh-bought jeans and making them your own. Just curious – have you ever bleached a pair of jeans to a lighter color? I’m considering doing so to the Everlane Cigarette jeans, but I’m definitely a bit nervous!
Hi Krystal! I haven’t tried that! I have tried multiple heavy duty washes in a row to fade the color a bit, but I didn’t have much luck with it — it just seemed to exaggerate the whiskering even more. I hear you on wanting to lighten those Everlane jeans though. I ordered them, but ended up sending them back because the wash wasn’t quite right. But I love your DIY approach! I’d love to hear a follow up from you however it ends up going. :)
I successfully bleached a pair of topshop jeans recently! Make sure they are laid out flat (like in a bathtub) or you will get uneven bleaching (learned that the hard way and had to bleach again so now i have super light wash jeans!). It also takes awhile, so don’t feel wierd about putting in quite a lot of bleach, I left mine sitting for at least 45 min.
So good to know, Ellen! Thanks for sharing — now I want to try it LOL. :)
So glad I checked back! Thank you for sharing, Ellen – I think I will go for it!
Thanks, Caroline! A question on the frayed hems: I have a pair that had perfect, lightly frayed hems when I bought them, like in your photos. But they’ve frayed SO much in subsequent washes (washing on cold, gentle cycle, air dry) that I no longer like the look. Do you have advice on maintaining that great lightly frayed look?
Hi Ali! I’ll occasionally trim fringe if it’s getting out of control. When you cut straight across it can look a little too perfect, so try trimming the fringe holding your scissors perpendicular to the hem, the way a hair stylist would trim ends to give texture: https://www.londonschoolofbarbering.com/point-cutting/ I hope that helps a little! :)
After trimming the frayed bits sew a straight seam where it hasn’t frayed yet to prevent it from fraying more than you’d like.
Thank you for all the awesome tips! I ordered that last pair of black ones you featured a few days ago and they just arrived today! So very timely tips :) I’m considering a sock bootie… any other ways you wear yours besides wide/straight bottoms? I often cut my own hems too… and use a little sand paper to rough up the edges :)
Hi Kate! Oh you’ll love them! They are the same ones as the last pair I featured in this post. And such a good idea with the sandpaper. :) As for sock booties — I like wearing them with midi skirts (like a pleated knit midi paired with a chunky sweater), mini dresses (sock booties and a long sleeve velvet minidress would be so good for a holiday event), midi dresses (like a minimalist loose sweater midi dress), even maxi dresses (sweeping floral maxi + sock booties = another holiday winner). And the black and cream booties in this post even go well with skinny jeans, though the brown pair in this post probably wouldn’t work well with skinnies since the shaft is too tall and tight.
I am loving this post! It’s taken me a long time to figure it out but I’m happiest with a pair of high waisted, straight legged, 100% cotton jeans. They remind me of my high school days in the 90s.
For socks, I love smartwool hiking medium crew socks but the last pair I bought kept sliding down my calf so now I’m at a loss for socks and don’t know if it was a bad pair. How thick are the socks you linked to in this post? I like a medium cushion for winter and want to find another option.
I am so happy high waist jeans are back. I am 5’9″ with shorter legs and a loo o ooo o oong waist, and I absolutely HATED the 2000s with those low-rise jeans! They simply did not fit my torso. My natural waist sits a good 2 inches above my belly button, so low-rise jeans were muffin-top central. Yuck!
Anyway, thank you for this post. Also loving the budget-friendly options under $90 :)
Thanks for the article!! I have been seeing the cut hems and love them! I will be trying my own now :).
Also, I would love to see you write an article featuring all American Made clothing! I am doing my best to find clothing to support the local grower, worker and company. I have found some wonderful companies that are buying American grown cotton and wool, manufacturing it in fabrics, and sewing them all in the wonderful USA!!
Hi Denise! I’ll start compiling a list! :) In the meantime, if you have time, would you share a few of those wonderful companies you’ve found? I’d love to hear your favorites. :)
I love your approach as usual! These styles are all so do-able and easy but have a little magic thrown in there. I’m definitely going to try some of these color combinations.
Love the fit on you!
Thank you for great post, Caroline! Always such a pleasure to dive into your texts and photos.
I have the opposite problem – have you or anyone tried shrinking new jeans (with elastane)? Just bought a wonderful pair that snug so perfectly, but after half day of wear loosened up half size and feels way too baggy in waist, hips and leg
Thank you so much Alexandra! :) Usually washing with hot water and drying on high heat will snap my stretchy elastane jeans back into shape (though it’s hard on the fabric). Anyone else have any suggestions?
I know the feeling! So annoying, right?! I usually end up returning and sizing down so they are uncomfortably tight at first, but then loosen to be just right :/ not a perfect solution. I’ve come to prefer jeans with really great recovery – that is, they snap back and hold their shape, rather than stretch out. Weirdly Target has jeans with great recovery – who knew! I usually buy them secondhand so it’s better for the environment and I’ve found they’re super easy to find it’s thrift stores. Good luck! ❤️
Thank you both for the replies! I tried washing on high temperature but I think it’s not a permanent solution. I might end up tailoring them down.
I usually buy 99% cotton to 1% elastane ratio, as they mold better and loosen up half size. But this time I got 98% and 2% and it’s a whole different game! I was actually thinking that it’s a pretty interesting topic to cover – jeans composition, sizing, molding and recovery. It’s different with every pair, right?! :)
My biggest issue with straight jeans in being petite (5’0)-Ive ordered many petite straight jeans and they all end up fitting like mom jeans. Any recommendations?
Try Madewell’s petite length options!
Christine W says
I cut my own hems a lot since I’m petite. I like the raw edge. So, what I do when I get a new pair of jeans that I want to have the raw edge or cut off some of the length is…
1) Put them on
2) Turn up the bottom to where I want them
3) Carefully, take off jeans so where I turned up the jeans at is still in place
4) Quick iron the turned up bottoms for an easy line to cut
5) Cut across the crease
6) Take tweezers or a pin to distress hem
Hope this helps!
Doesn’t the frayed hem keep fraying every time you wash the jeans?
Thanks for any advice!
Katelin Carter says
love the h&m sweater! what size are you wearing?
OK you have sold me on trying high-waist again! The ones I tried before were just too tight and uncomfortable.
Do you think the waistband stretching method would work for jeans that have some stretch? Right now I’m post-partum and my pants fit me everywhere except the belly, it’s so frustrating. I’m a different sized waist than the rest of the pants.
A seam ripper works well to help coax the cut hems out. Just fray the edges yourself while pulling a few threads.
Your jean stretching tip came at the perfect time for me. I just tried it on a new pair of Everlane jeans that were a little too tight in the waist, and it worked perfectly. Thank you!
Love all the jeans and boots combined make the perfect looks.The boots in look 2 are gorgeous!
Aimee Guzman says
I was hesitant about this trend but I feel like I could be into it after this post! Do you think these style jeans go best with a heeled boot or would a flat one look okay?
Katie S. says
Love this post, and love straight leg jeans.
I also recommend the Levi’s Wedgie Straights! They are non stretch, and have a great straight leg, and nice high rise.
Question for one of my style icons: is there any way to style high waisted boyfriend jeans (frayed or cuffed) with shooties (those short shoe-boots that stop lower ankle). I love this style of jeans and wear them 8 months of the year in Alabama with either Eileen Fisher sport sandals or Greats sneakers. But I have nothing in my current shoe closet (including knee high boots) that works and I hate cold ankles! Are my only options buying this type of boot above or retiring my faves til March?
Hi Angie! You’ve definitely got options besides buying. :) I love socks peeking out between jeans + boots, so that could be an option! Check out this post from a couple years ago — it’s all about wearing socks and ankle booties. :) http://www.un-fancy.com/outfits/fall-outfits/how-to-wear-ankle-booties-with-jeans-part-ii-socks/ I hope it’s helpful! :)
Love this post! So inspiring. I am so sick of cold ankles! Question for you…I loved the free people Cecile boots you wore in your 10×10, but you didn’t include them in this post. Are they slim enough in the shaft to fit under straight jeans?? I love the ones in this post but don’t want to spend that much. Thanks for your time!
Hi Nikki! I’m wearing the Free People Cecile booties in the 3rd outfit of this post. :) They fit great underneath straight leg jeans!
Davinia Cavaney says
Do you happen to know whether the Byfar Lada boots are just for sale this season or whether they are available all year? I can find photos of them from 2017 so thought they may perhaps re-stock them. I Don’t think I can afford them right now but would love to get them for my birthday in March.
Hi Davinia! I’m new to the brand, so this isn’t 100% positive, but from what I can tell it looks like they do restock regularly and carry the same styles for multiple seasons. By March they might even be marked down! Crossing my fingers for you. :)
Patricia D Halloran says
great post, thanks! i have had trouble with straight leg jeans but have not tried them with the ankle boots, awesome tip! Question, my stretchy straight leg jeans bag so much at the knee (within an hour of putting them on) that it looks bad, do you have that problem with the Topshop jeans? i’m curious to try. Also they’re on sale for $45 right now!
The Topshop pair does stretch at the knee a little, but it usually takes 3-4 wears before it gets noticeable. Not too shabby!
I’ve been wanting to try the straight denim with the high ankle boot for some time, but have had SO much trouble finding a pair that fit me correctly. After finding your post, I ordered the Topshop ones from your first look and I haven’t been this in love with a pair of denim in quite some time. They fit perfectly – I ordered them immediately in two other colors. I’m about to cut the hems as well. :) This post is a godsend, thank you!
Hi! This post has inspired so many purchases for me :)
I want to buy the HM sweater featured in a few of these looks. I can’t find it in store to try on for size, so I’m wondering what size you have on? I’m typically a size small but don’t want the fit to be too tight. Do you have a recommendation for me? Thanks.
Hi Anna! I got an XS — it runs pretty loose. :)
Caroline, do you have any further tips to share on stretching the waistband of the non-stretch jeans? I’d appreciate your help. I have the same Other Stories jeans. The hips and legs are fine, but I would love to stretch the waistband a good inch or two. I buttoned the damp waistband around an object that was a snug fit until they were dry, and there was no difference.
Also, have you washed the jeans since stretching them? I always wash jeans in cold water and line dry, and they always tighten up a bit. Great for snapping eased jeans back into shape. But I’d hate to lose a hard-earned stretched waistband!
Joanna LaFrance says
Hi Caroline! Found this post on Pinterest. I love every pair of jeans you posted but all the links look old/sold out. Is there anyway you can help me find these jeans from more recent sellers? I would greatly appreciate it!!!!
Hi Joanna! Sure thing, I’ll do an updated jeans post soon! :)