Reader Request: When to Cuff Jeans

cuffing jeans

left | right

Reader Andrea e-mailed me this question:

I wondered if you would do a blog post about when and when not to cuff jeans. I think doing so would add a little something to my limited casual wardrobe. But I can’t figure out what where to use it. Or maybe it is to be done with a certain jean style. I feel like I’m missing something with this look.

I am late to the cuffing game myself, but have really enjoyed playing around with this styling trick over the past few months. One thing that I think makes cuffing tricky is that it looks great when it’s a little messy … but artfully messy can actually be harder to re-create than neat. Here are a few things I’ve learned from my own tinkerings:

Skinnies, straight-legs, or boyfriends

This may seem obvious, but it’s worth mentioning. You want the cuff to be fairly small and close to your ankle/calf, so anything that flares out toward the hem like a bootcut or has a wide leg like a trouser cut won’t work. Boyfriend jeans are cuffed more often than not, but you’ll notice that although the jean is loose-fitting the leg tapers and the cuff is fairly close.

Why we cuff

bad jeans cuffs

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Here are two cases in which I think cuffing would actually improve the overall look. Tucking even the skinniest of skinny jeans into ankle boots looks a bit odd, and can cause uncomfortable scrunching. Skinny jeans that haven’t been hemmed to ankle length will bunch and pool at the ankle – cuffing eliminates this problem.

Cuffs that aren’t quite right


left | middleright

Now, listen: The Cuff Police don’t exist. If you can’t get your cuffs to fall just so, that’s completely fine. The likelihood of anyone doing a trend-focused ankle check is slim to none. But just in case you’ve been trying to cuff and can’t figure out what’s off, here are a couple of examples that don’t quite hit the mark.

To my eye, the pair on the left has been cuffed just a wee bit too high. You want to show the curve of your ankle, but don’t need to get up into calf territory. In the middle, the messiness of the cuff is fine but they look mighty bulky. This is an issue that I have with some of my jeans: Ideally you want the cuff to be narrow and relatively flat. This means that cuffing jeans hemmed long will backfire, and cuffing ankle-length jeans will work better. And on the right, you have a super tall cuff – this is a fringe trend now and may eventually become the norm. But it still looks a little funky to most folks.

Cuffs with ankle boots

ankle boots cuffed jeans

left | right

NOW we’re talking. Personally, this is my favorite look for cuffing – with ankle boots or other ankle-height shoes. Let just a sliver of ankle peek out between where the cuff ends and the shoe begins. My ankles get weirdly cold, so I will sometimes do black booties, black/gray striped socks, and cuffed jeans. You want to see where the ankle curves in, but you can still see that with a close-fitting sock in the mix.

Cuffs with heels and flats

cuffed jeans with heels

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Cuffed jeans and pants can also look chic and fun with low-vamp shoes like pumps and or ballet flats. Again, remember to cuff just above where your ankle curves, no higher. This is especially important since you’re exposing more of the foot with a low vamp, and if your cuff is high it will give the impression of crops or floods. Cuffing with this style of shoe is helpful if you’ve got a pair of skinnies that pools at the ankle, as mentioned above.

Cuffs with sneakers

cuffed jeans with sneakers

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And finally, sneaks – a great match for cuffed jeans. Cuffing creates an instantly casual look, and sneakers are naturally casual so they play well together. In this case, I’d avoid socks. You want a bit of bare ankle peeking out between the high vamp of the shoe and the cuff of the jean. Slip-on sneakers work just as well.

So which shoe styles won’t work with cuffs? Mary Janes look awkward because between the vamp, strap, and cuff, your foot is cut into three pieces. Mules are a bit odd for similar reasons, especially heeled ones. And, of course, anything that reaches above the ankle like a tall boot won’t look quite right, though I’ve seen people experimenting with tall-shaft ankle boots tucked under cuffs.

Kind of a lot, right? Again, these are not rules, merely guidelines. And they’re MY guidelines, so you may hear completely different advice from other folks. In fact I sent Andrea to this post which has some overlap, but also shows a cuff that’s much wider than I’d wear or recommend. This styling trick is very fluid, so don’t be afraid to play. If you find that a higher or lower cuff looks better to your eye, go for it. If you like the look of a thicker cuff, go for that, too. Do whatever feels and looks best to you.

Anyone else playing around with cuffs these days? Where do you like yours to fall? Are you more apt to cuff skinnies, straight legs, or boyfriends? All of the above? Other tips to share?

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Originally posted 2014-10-22 06:10:13.

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12 Responses to “Reader Request: When to Cuff Jeans”

  1. Nebraskim

    I wouldn’t probably ever do this myself but I do find the last looks, rolled with sneakers, to be cute. I have never adopted the jeans with heels look, especially jeans with pumps and high platforms (because I never wear this type of shoe) but I can appreciate it on others. Over on You Look Fab, Angie is chatting about rolled jeans and the sock possibilities today.

  2. Wockyjabber

    I’m all about the cuff. I do it to my boyfriend and straight leg jeans. I pretty much do it all the time unless I’m tucking jeans into a tall boot.

  3. Lisa Wong

    This trend works so well for petite gals who can’t be bothered to hem their jeans by an inch or so. I cuff my jeans to keep them from bunching and pooling when worn with ankle boots. You’re spot on about emphasizing the sliver of bare ankle: it makes the look!

  4. Anamarie

    I have so-called skinny jeans that are actually skinny-straight leg jeans.. I do the 80s cuff (fold the leg over itself a bit, then cuff) which looks neater to me than just the straight up cuff. I like this look with flats and brogues. I would say that the jeans I cuff are slightly shorter than the first set of images, right photo. I do a thin cuff, so there’s only about an inch or so of ankle showing above the shoe.

    • Amy Blankenship

      I have to agree that a description of the 80’s cuff would not have been out of place in this post. I found a few of these pics had the cuff looking a bit lumpy. I think that cuff style looks less lumpy.

  5. crtfly

    I like the cuffed jeans with sneakers look the best. I have a real problem with the skinnies tucked into the ankle boots. That combination looks to me like a blue-legged, hoofed, antelope type creature who roams the plains of Africa. No insult to the model intended. It’s just what the combination of clothing brings to mind.


  6. girlinagreendress

    Do you have suggestions for how to do this whilst wearing socks? I like the look of cuffing but I really don’t want drafty ankles or bare, sweaty feet in my shoes. I’ve seen suggestions that you can cuff your trousers (or wear ankle grazers) if you have cool or interesting socks to show off, but I can’t really get this to look right for me.

    • Sally McGraw

      I’m afraid I don’t have any specific advice on cuffing with socks … when I do it myself, I do it really subtly – in a situation where the cuff is very close to the top of a bootie, for instance. I’m with you on the drafty ankles, though. It’s amazing how cold it can make you! This post shows a few examples with socks, and they’re definitely meant to be shown off: Honestly, I think it’ll just take some experimentation. Try socks with booties, then with flats/oxfords, try different cuff lengths and heights … hopefully you can land on a formula that works. Sorry I can’t be more helpful!

      • girlinagreendress

        Thanks, there are some good ideas at that link. I’ll keep experimenting – it’s probably a good excuse to go and buy some really nice socks!

  7. Ginger

    I don’t mind the messy cuffs but I don’t want them coming unrolled halfway through the day.

  8. Cherene Francis

    Great post! I love the cuff and ankle boots look. I’m petite so I am very careful with how I use cuffs because they can make you look shorter. I usually wear heels if I’m going to wear cuffs.