The best high-waisted jeans for vintage and pin-up style

The best high-waisted jeans for vintage and pin-up style
A decent pair of high-waisted jeans is an absolute staple in my wardrobe. Yet a good pair can be very hard to find – particularly if you’re looking for a true high waist for a vintage shape and not what the high street might think this is. Try to find a pair with belt loops and pockets and not these jegging/disco types that are popping up everywhere and your mission becomes even more difficult.
Because I’m petite and my torso is shorter than average, I tend to go through the rounds when I’m trying to find a pair of high-waisted jeans that suits me. As such, I’ve tried so many on recently I feel I can give tips on where to find a pair now! This includes those that didn’t work for me, but might for other ladies. Throughout this round-up, I’ve tried to indicate which sizes and shapes I think would suit each pair.
The best mid high waist jeans for pin-up and vintage style
These are the rises that hit you at approximately the bellybutton – ideally on it. For a more traditionally vintage higher-waist than that, keep reading onto ‘true high waists’ below. These styles will be especially ideal for my fellow petite ladies, or anyone who’d like a hint of vintage style rather than complete authenticity. They also all have skinnier legs than the true highs below, so would be better for a more modern pin-up than authentic vintage look.
These pairs have made it onto my list because they are the best that’s currently available, to my mind..
These are currently my favourite pair of jeans – and at the moment they’re edging towards the lofty heights of being my all-time favourite pair. They hit me at just above my bellybutton and do the most amazing job of holding everything in and giving a fantastic shape. I don’t have a flat tummy and many pairs of high-waisted jeans emphasise its roundness, but not these! The denim is firm enough to pull me in without being uncomfortable – they even seem to give me a small waist and smooth hips. It’s jean voodoo, I tell you.
So why even have more options on this list? Well, I adore them and the reviews on the website would suggest I’m not alone in that, but if you’re tall and want a naval-high waist these aren’t for you. They only come in standard leg length, so they’ll be ankle crops if you’re used to 34″+. I also have to be frank that these are the priciest pair here and not everyone will want to spend that on jeans. For me, I got them for £20 off on special offer and they are so ideal I am completely happy with the investment – they are fab quality (something I wouldn’t always say American Apparel is).
Ideal for: all shapes, due to large amount of stretch, which helps to give a perfect fit; petite (with roll-ups or alterations) or average height
Order: your exact waist measurement. These are super true-to-size, although I did find I could get into the next size down too – it just wasn’t as comfy. I have found these stretch out just enough without going saggy, which I guess is the sign of quality denim!
You’ve seen me wear these jeans before, so it’s probably not a surprise they’ve found their way onto this list. I still love them for their quirky western-style stitching and the classic indigo shade. Although, again, they’re not going to be long enough for tall ladies.
There is another drawback with these jeans too – and now that I’ve stretched them a little bit through wear it’s the reason I sought out my new American Apparel pair… They do gap at the back on me. My hips are 8″ wider than my waist, which isn’t super curvy, but probably curvier than some. Saying this, I am squarely between sizes in these jeans, so I feel like if I could have bought a size 9 I wouldn’t have had a problem with this as they’d have given in the hips and still fit at the waist. Brand new, these were too big at the waist, so it figures that’d get worse!
Ideal for: those with around a 6″ or smaller gap difference between waist and hip measurements; petite (with roll-ups or alterations) or average height
Order: a size up rather than down, as these come up a half size small (and not in a way you could stretch them to fit easily – I could do the size down up, but it made me want to cry!)
Ankle (or petite!) length – Collectif Sally Denim Capris
I love this style, even though it is the only pair in this round-up that breaks my usual requirement of jeans, having no pockets or belt loops. This being said, if these had fit me correctly I would have kept them in a heartbeat as they would have been flattering and could have been dressed up quite nicely due to the smooth pin-up shape. They also would have been very versatile on my short self – I could have worn them as both full length jeans that would have been an ideal length, or rolled them up. They are, you see, intended to be ankle length.
Alas, though, I’m an inch bigger than I could get away with on the waist for these. I tried two sizes on – the size up was much too big, the smaller size (my usual Collectif size) fit but not comfortably. The waist was just a bit too small – I couldn’t sit down in them without grimacing. While they do have a bit of stretch, it wasn’t enough for me. The discrepancy wasn’t the same as the Rebel Kate – these come up smaller than the Sally.
Ideal for: hourglass shapes who fit squarely into Collectif’s size guide measurements; petite – for wearing as full length jeans – and average and tall for wearing as crops
Order: your size as per Collectif’s size guide, if you fit into it neatly – these won’t be comfortable if your waist is bigger than said guide (mine is 1″ bigger)
I’ve owned a few pairs of New Look high-waist jeans in my time and what I can say for them is this: they are a very good price for what they are, and what they are is a budget high-street option available in many sizes and colours. New Look are the only popular high street retailer I’ve found that are still producing high waist jeans, rather than high waist jeggings. This particular style they seem to reissue each season and it’s currently available in various blue shades and black, in as many as four different lengths. The three-button thing is quite similar to the appearance of Collectif’s Rebel Kate style.
They’re a decent option if you want to try out a pair before investing in a better quality one, as the downside to these is that the super-soft materials do tend to stretch a bit over time. Saying that, it can depend on the pair as I’ve got some that have kept their shape pretty well. With a waist belt it might not be worth worrying about.
Ideal for: all heights, as the various colours usually come in 3-4 different leg lengths, and as they are very stretchy they’ll fit most shapes
Order: New Look come up slightly on the large size I find – I’m between sizes as I’ve mentioned and I always order the smaller size in their jeans, which serves me well. Because of how much stretch there is in their jeans, you’ll probably find erring on the side of small will serve you best
The best true / super high-waisted jeans for vintage and pin-up style
So these are the jeans that will sit above the belly-button, in a higher, more authentically ‘vintage’ rise. The high street doesn’t tend to go near rises this long!
For authenticity: Freddies of Pinewood (any – Indigo Pleated Pants featured)
I wanted these jeans to work for me so badly, but they just didn’t. These jeans probably have the highest rise of any on this list, sitting on me around the bottom of my ribcage. And that’s why they didn’t work – a waistband restricting your ribs is pretty uncomfortable! I am, however, pretty short and I know dozens of ladies these jeans work wonderfully for. No vintage jeans round-up is complete without this brand, known for their faithful reproduction of vintage styles. Most of their styles therefore feature a classic wider leg than the skinny types we’re used to these days, so these are more for your vintage look than your pin-up one.
Saying all of this, Emileigh (Flashback Summer) had the rise of her pair altered and at approximately my height she’s rocking them, so that’s always an option too – if you’re prepared to invest, these jeans don’t come cheap as it is.
Ideal for: average-tall ladies, ideally with measurements close to the size guides as these are classic denim with a limited amount of give. Note that each style fits slightly differently
Order: stick to the size guides, but if you’re not sure the Freddies team are always willing to help!
These are a pair I haven’t tried on, as these jeans are specifically for those of us who have a tiny little waist and comparatively larger hips – we’re talking 10″+ worth of difference. However, regardless of this they’ve made it onto my list because I’ve never seen a pair of jeans raved about in the way these ones are by vintage/pin-up lovers! I have a small amount of difficulty getting jeans to fit on the hips and not gap at the back, but I understand for those of us with a bigger discrepancy than my 8″ waist-hip difference this is a real problem that puts most of you off buying them entirely. I urge you to try these out – and if you want to see how they look on and hear more from someone who knows check out Miss Victory Violet’s review.
The other reason I’m recommending these jeans is because of how lovely and helpful the owner is. Any questions about sizing she’ll happily help you out with and these jeans come in both 32″ and 36″ lengths for tall ladies. And if you want to try a non-curvy version, there’s a ‘classic’ style too. I would say that there’s probably cheaper options in this post for those of us with a smaller discrepancy in measurements, but if you’re curvy maybe these jeans are the answer!
Ideal for: curvy girls, and if you’re average height or tall you won’t have to get alterations
Order: from speaking to the owner, it sounds like you should go for the size closest to your waist measurement, as the whole point of these jeans is they stretch to fit even the curviest hips, while the waist should be snug
Like Freddies, but cheaper: Collectif Monroe Full Length Jeans
Another pair that I tried and sent back, as I again couldn’t get the especially high rise to feel comfortable on me. They’re very cute though, and quite similar to the Freddies pairs in style with their straight leg – although I’d say it’s narrower than most Freddies pairs. These are a good, cheaper alternative to the Freddies if you want to try this more classically vintage shape out.
The dark denim is going to be super flattering on most people too!

Ideal for:
probably going to be better for more subtle hourglass curves, as these don’t have a huge amount of stretch. They fit me fine on the waist and hips, but would probably accommodate slightly bigger hips than mine
Order: follow the size guide, it’s quite accurate for this pair. If your waist is much bigger than the size guide, you might want to size up
Also, one final mention for the Vivien of Holloway 1950s Jeans. I haven’t featured them because I don’t know how they fit and the measurements are definitely on the curvy side so I don’t think these would work for people like me. For example, a 26W has 38H… but I’m going to guess without the figure-hugging stretch of the Lady K Love jeans. They’re also pricey, so you’re going to really want them to look perfect for that money! They get bonus points for the range of colours though, and how authentic they are.
And what to avoid…
These are of that ‘disco jean’ variety with no pockets or belt loops, which is the first reason you should avoid them (although, as above, sometimes I can go for these if they fit nicely as per the Sally Capris). The second is I’ve never looked as bad in a pair of trousers as I did standing in the excruciating light of the Topshop changing room wearing the Jonis. They highlighted every unflattering thing possible – from my round tummy to the weird baby saddle bag I have on one hip. Basically, the material is thin and doesn’t have the suck-it-in quality of good stretch denim, as per the American Apparel jeans above. I can only picture these working for the slim among us with no lower body insecurities. I’m actually pretty positive about my body, but after I put these on I felt dreadful about myself for a week afterwards. Also, they call these ‘super high’ but they’re not as high as the styles in my ‘true high waists’ above, so don’t be fooled.
By all means, do leave any other suggestions for your favourite pairs below! Have I missed anything obvious?


  1. Lisa
    September 15, 2015 / 4:15 pm

    Thank you for sharing. I got a pair of high-waisted jeans from ModCloth awhile ago and they changed my life. Seriously, they are amazing for my shape. Low-waisted jeans always gapped on my because my waist is much smaller than my hips and butt. I will have to check these out!

    • ciciadmin
      September 15, 2015 / 7:40 pm

      I wondered if anyone was going to mention ModCloth's jeans! I nearly included them as a mention, but I've got no experience of the brand at all, so it wouldn't have been particularly helpful… Thanks for mentioning 🙂

  2. September 15, 2015 / 8:22 pm

    It is so hard to find a pair of jeans that fit! Throw in a high waist factor to that and my head is spinning! This is an awesome roundup though and provides a good place to start for someone like me who really has little to no experience. 🙂 Thanks for posting this!

  3. September 15, 2015 / 9:59 pm

    Amazing post! Props to you, jeans are so damn hard I have currently completly given up trying (it usually ends in tears).

    • September 18, 2015 / 12:27 pm

      I think it helps that I'm not particularly pear-shaped, so I don't have the kind of issues I imagine those of you with a bigger waist-hip ratio than me have!

  4. Amanda
    September 16, 2015 / 12:26 am

    Thanks so much for the kind words on my blog! I love this post – it is so helpful to me… I have the Collectif jeans and I had the same problem with them stretching and can barely wear mine anymore too. I have shopping anxiety when I am looking for jeans because I have had so many not work out. I am so happy you wrote this post so I can try some of your favs since you're petite too!

    • September 18, 2015 / 12:28 pm

      My pleasure and glad you like this post 🙂 I do recommend the American Apparel jeans highly for petite ladies looking for something that doesn't sit somewhere near our chins 😉

  5. September 16, 2015 / 9:05 pm

    Great post! I've been slowly venturing into high waisted jeans over the past year or so. So far I've had good luck with ModCloth, but I was flying blind! This is a great post for future reference! XO
    -Lauren Blair

    • September 18, 2015 / 12:29 pm

      Thanks! I would like to try the Modcloth ones, but I don't feel very savvy about Modcloth sizing at all!

  6. September 17, 2015 / 4:15 pm

    I love high waist jeans <3 They are so comfortable & love the vintage effect that they give! I have a few pairs, one of them is from Dorothy Perkins while the rest are from the USA. I'm looking to add a few more to my collection, so thanks for this post!!!

    Kisses <3

    • September 18, 2015 / 12:30 pm

      I always struggle with Dorothy Perkins – their stuff never fits my body shape ever!

  7. September 18, 2015 / 8:54 pm

    Thoroughly awesome and wonderfully detailed post, sweet CiCi, thank you for penning it. As someone for whom pants have always been the trickiest garment to nail, I read this with great interest and am very intrigued by Lady K Love's denim now. Perhaps one day I'll splurge and try a pair. I've had good experiences – knock wood – with Freddies, so maybe luck could strike twice with repro/vintage style denim brands from the UK.

    Tons of hugs & happy weekend wishes,
    ♥ Jessica

    • ciciadmin
      September 20, 2015 / 10:06 am

      I've only heard good things about Lady K – and even better, that she's currently making a petite pair…

  8. September 19, 2015 / 1:49 pm

    Thank you for writing such a detailed post. I found it very interesting and informative. I have never worn jeans – in fact I only started to wear trousers two years ago. I have never been too sure of the image of jeans – maybe because I am not a fan of denim – but I am being persuaded to buy a pair by my friends and now my young daughter.

    I am told that a pair of Levis Curve would be ideal for me – although fairly expensive I understand that they are good value and a good fit.

    I have not given in to pressure yet but one day soon I may try a pair.


    • ciciadmin
      September 20, 2015 / 10:07 am

      I think the key is getting good denim – I find a real difference between the cheap and more expensive stuff.

      I've not tried Levi's for years but I used to live in them… The good thing about them is the variety of sizes!

  9. March 30, 2016 / 6:59 pm

    I had been considering Freddies, but after reading this I am going to stick with my LadyK which I do love. I am petite, and they are quite long, but I double cuff and am ok. At the end of the day, the do hit in an uncomfortable way, but I am ready for PJ's by then anyway. I may try the Collectif want a pair to hem into Capri length…maybe that's the pair.

    • ciciadmin
      March 31, 2016 / 12:12 pm

      I did find the Monroe Collectif style quite high waisted – it wasn't a good fit with my shape. But, you can always get alterations…

  10. September 5, 2017 / 1:16 pm

    Wow, this is probably the most complete and useful comparison post of high-waisted, vintage style jeans I've ever seen. Your fit notes are so helpful, even for those with different body types (super tall, 10" waist-hip difference here!), and now I'm feeling way more confident about choosing a brand to invest in. My last 2 pairs (Freddie's dungarees and Steady Clothing's high waist black jeans) weren't quite perfect, so I'd been a little trepidatious about ordering another pair online without the chance to try them on. Thank you for this post, because it's still helping people two years later!

    • ciciadmin
      September 5, 2017 / 1:26 pm

      Really pleased to help! Thanks for leaving a comment 🙂 Since I wrote this post Collectif have come out with a super high waist style that might be worth looking into, I think it's called 'Nomi', but the Lady K Loves pair are still a real fan favourite!

  11. Carmen Lee
    February 5, 2018 / 5:59 am

    I’ve been on a ‘Holy Grail’ of sorts search for high waisted jeans that hit me at my true high waist(smallest part of my waist)… I was excited when I found this article because it helped me to narrow it down. Unfortunately I tried the Monroe Collectif Jeans and they hit me right at the belly button…which is where I HATE jeans to go lol… I have yet to find zip/button front jeans that go up to my natural waist. I assume I must have a very long torso which is weird cause I’m not tall by any means. Anyways…I was just curious if anyone out there knew of any jeans that maybe be high enough waisted for me?
    What I’ve found that I must need is about a 14″ -15″ front rise…most I can find are only 12 or 13″…the Monroe ones were 13″ and hit right at my belly button so I’d love a couple inches higher to be flattering/hit at my natural/smallest part of waist. Any help would be greatly appreciated as it’s been at least a 5 year search so far! lol
    Sincerely, Carmen

    • CiCi Marie
      February 5, 2018 / 1:08 pm

      Hi Carmen, since I wrote this post Collectif have released the Nomi style, which I hear is super high waisted – but not the ‘traditional’ style of the Monroe. It might be worth your trying the Freddies of Pinewood styles as I felt like they came up about an inch higher than the Monroe on me. They’re probably the highest rise I’ve tried (they hit me on my ribcage and I couldn’t breathe!)… Lady K Loves I would guess may be similar to the Monroe, at least in as much as that’s how I found that fit. But other than that, I’m not aware of any new kid brands on the block as far as jeans go… Hope that helps!

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