Reader Request: Tucking Pants Into Boots

Several reader requests rolled in for guidance on pant-tucking. There were enough such requests that I’m gonna tackle this issue, even though I’m not much of a tucker myself! Please feel free to give your two cents in the comments if you have other tips or personal preferences to share … but to get us started, here are my opinions and observations about this extremely popular pairing.

Despite its pragmatic appeal to those of us living in climates prone to sloppy-wet weather, and despite seeming like an easy way to spruce up a pair of jeans, this style can be tough to pull off. Truly. So consider skipping it …

  • If you are at all self-conscious about calf width or overall leg proportion: Unless you are extremely careful about where those boots hit your leg, you may end up creating some inadvertent disproportionality. You might make your legs look stumpy or your calves look wide … and if you live in fear of such things, it you might not want to monkey with this look.

  • If you have trouble getting your boots zipped: Jamming some nice, thick denim in there isn’t gonna help. You can certainly tuck jeans into wide-mouthed and/or shorter boots, but the look is generally sleeker and more flattering with tall zip boots. (More on that shortly.)
  • If you own nothing but flares: All that extra cloth at the hem? That’s gonna end up wadded up on your ankle bones. Not comfy.

I do NOT believe this style to be the exclusive domain of tall, slender women. I’ve observed women of all body types tucking their pants into boots, and the ones who pull it off best are the ones who pay careful attention to how it affects their overall proportions. Petite women with thick calves who shove their jeans into short Uggs don’t fare nearly as well as petite women with thick calves who pair dark jeans with tall, slim-fitting dark boots. But I’m getting ahead of myself … just wanted to say upfront that anyone can do this. It’s just a question of doing it carefully.

As I mentioned above, I feel like this look is most successful with tall, zippered boots. You want to show off the shape of your entire leg, and a tighter boot lends itself to that kind of show-offery. Behold S. of academichic:

Her tall, fitted boots are dark, and so are her jeans. She is basically creating a single long line from her waist to her toes – generating an illusion of mile-long legs. Nice!

Audi of Fashion for Nerds goes a completely different route. Not only are her boots a contrasting color, but they are shorter, non-zippered, wide-mouthed cowboy boots. And I’ll level with you, my friends: This look works for Audi because her legs are extremely long and extremely slender. If I tucked my jeans into a pair of mid-calf cowboy boots I’d look like one of the seven dwarves about to head down into the mines. It can certainly be done, but is best left to the most willowy of women.

Much shorter wide-mouthed boots can work, too. If the curve of your calf is visible, that pairing can be flattering. If you go this route, choose a boot that hits just above the ankle.

From what I’ve seen, heeled boots will work best for petite and average-height women. Since you’re dividing your leg in half at the knee, any added height is beneficial. Heeled boots will also create a more ladylike, sophisticated vibe, whereas flat boots may scream “equestrian,” “Harley enthusiast,” or “fisherwoman.” But a modern flat or slight wedge on a taller wearer can look chic and sleek. All down to taste and comfort level, as always.

Again, as noted above, flares will not work. Bootcuts will be fairly uncomfortable. Even straightlegs will bunch a bit when crammed into jeans. You’re basically gonna need either true skinnies or close-fitting cropped jeans.

Clare of Between Laundry Days. looks fantastic in her super sexy, super tight gray skinnies tucked into tall brown boots. Notice that, even on a woman as slender as Clare, there is some bunching around the top of the boot. That is totally fine if you ask me, and, frankly, entirely unavoidable.

Cropped jeans will alleviate potential ankle-bunches, but still need to fit closely to the leg … and be long enough that they don’t constantly pop out of your boot tops!

Non-jean pants can also be tucked into tall boots, of course, but the same rules apply: Skinny, or close-fitting and cropped. And, ideally, a color that is close in value to that of the boots.

This is down to your comfort level, friends. In an ideal world, you’d wear a top that ends about three fingers above your crotch point – a flattering length for shirts worn with pants. Again, since the boots lop off your legs at the knee, you’ll need to create some counterbalance by showing the maximum amount of leg. Otherwise, stumpification may ensue. But if you, like me, would rather be thrown into the rotating barrel of a cement mixer than reveal your hips and butt encased in a pair of skinnies, go tunic. Go short tunic, but go tunic.

You can also try a shorter/more fitted top with a longer cardigan, coat, duster, blazer, or other outer layer that will shield your bootay from prying eyes.

I don’t own skinnies or close-fitting crops. And honestly, I tend to look like a disproportionate, unhappy poseur with my jeans tucked into my boots. So I generally go this route instead:

Just like Erin of Work with What You’ve Got, I’m partial to tucking my nice thick, stretchy, soft LEGGINGS into my tall boots. And, generally, black leggings into black boots for optimum leg-flattery. There’s no bunching, it works with flat boots even if you’re a shortie, and tunics work perfectly. Much more to this curvy girl’s liking, thank you very much. (Though, as you can see, it looks fabulous on considerably less curvy Erin, too.)

Hope this little tutorial was helpful … holler if you’ve got any other tips to contribute, or questions left unanswered. As I said above, I’m not exactly an expert on this topic, so all suggestions, recommendations, and personal preferences are welcome. Let’s hear ’em!

Top image courtesy Malingering.

  • kpriss

    I'm not a tuck'in girl. Though my willowy self could go just fine with the look, it just doesn't sing the right tune to me. I don't wear skinny jeans/pants anymore, hardly any leggings so tucking in gets a bit rough with ordinary boot cut jeans.

    Give me wellies and I'll wear them anyday, tuck my jeans in, my velour pants, my leggings. My favorite casual no-pants thing is dark wool tights with dark high boots and my husband's stripey shirt. Generously biiiiig it fits like a glove. Not to precious, not too casual, just what it takes (and no pants! :D)

  • Jenny

    What about those jean leggings – what are they being called – skeggings or something? Oh, jeggings. I thought they were ridiculous at first but now that I think about it, since I DO wear skinnies tucked into tall boots, why not jean leggings? As long as they look more like jeans and less like leggings, if you know what I mean.

  • Deborah

    "I'm partial to tucking my nice thick, stretchy, soft LEGGINGS into my tall boots. And, generally, black leggings into black boots for optimum leg-flattery. There's no bunching, it works with flat boots even if you're a shortie, and tunics work perfectly."

    But where to find these awesome thick, stretchy, soft LEGGINGS??? Do you have a good resource? {pleading}

  • Laura Elaine

    I normally don the skinnies for boot tucking (too shy for leggings meself:), but a friend of mine has several pairs of skinny/slim capri jeans just for tucking purposes. She finds they work quite well and don't bunch at all!

  • Sal

    Jenny: Hmmm. Jeggings do seem ideal, but since they offer less coverage than actual jeans, I'd say approach with caution. I'd still treat jeggings as leggings and recommend that you wear longer tops and tunics with 'em. But I'm a fairly modest gal. Anyone feel otherwise?

    Deborah: Gosh, I get mine at Target, mainly! I've also ordered American Apparel leggings, and they're incredibly soft and durable. The AA versions will last longer, I'd bet, and you can get them at a discount on Amazon.

  • Meli22

    I wear boots with anything but flares. I have bootcut and straightlegs, and they fit in my boots. I pick boots with a little extra room in them, #1. They have to hit a few inches under or up to the knee, so the bulk can hide. My slouchy brown suede boots fit my bootcuts better- I take a section on the side of the pants, and fold them around. The fold hides on the side towards the back. My black boots are a bit more fitted, so I go with straghtlegs. I only have 1 pair of semi-skinnies, (bootcut but fit like a skinny almost)and I have not worn them anywhere yet.

    I have thick claves, and I find a nice straight boot makes my thick calves look slimmer, especially when they are dark in color.

    black boots, straightleg pants folded around:

    brown slouchy boots and bootcut jeans:

  • jennine

    i can't imagine NOT tucking in, unless we're dealing with ankle boots. even then, it really depends on the pants i'm wearing.

    then again, i wear an awful lot of skinny jeans and leggings.

  • Christina Lee

    good one, Sal. I tuck my crops into boots or leggings. I do want ot find a comfy pair of Jeggings though!

  • Deborah

    Thanks for the recommendation Sal!

  • hope505

    omg yes! I totally forgot about the leggings/boots combo! *heehee!* Thanks for reminding me about that!

  • Melissa Blake

    OK, I just fell in love with the dog in that photo! :)

  • Anna

    Can you give some advice for us short, curvier girls on how to wear/what to look for in a tunic?

  • Sal

    Anna: You bet! A petite curvy woman who wants to sport this look would be best served to try one of these tactics:

    1. Monochrome: Black boots, dark wash or black jeans/leggings, and a black or charcoal tunic. If you look dreadful in black and gray, either go for a very dark color – deep purple, brown, or green – or use a bright or patterned scarf up near your face to mitigate the unflattering darkness. Speaking of which, since a wash of black is pretty dull, be sure to lean on your jewelry and accessories to jazz up this look.

    2. Shorter length tunics: If you’re petite, you’ll want to expose the maximum amount of leg. Within your comfort zone, of course! Try for a hand and a half below crotchpoint, or two hands if that just feels risqué.

    3. Fitted tunics: Again, this is down to comfort level, but try to find a tunic that shows off your waist a bit. A giant boxy tunic that masks your curves is not gonna be flattering. You can experiment with belting, too, though that can be tricky.

    4. Side slits: I looooove side slits in tunics because they let my hips move! This will help any curvy woman – petite or not – to walk comfortably in a tunic.

    5. Sweater dresses: I consider sweater dresses to be in the tunic family, and they can be far sexier because they’re thick but have some cling. If you can’t find any straight-up tunics that work for your bod, explore some shorter length sweater dresses. They look amazing with leggings and tall boots!

  • Michael McGraw Photography

    The look I usually sport when wearing jeans and boots is to have…just the back..of one pant leg tucked into the boot, which needs to be untucked every time I get out of my chair.

    It's a look the males in my family have been sporting for generations.

  • pretty face

    I am an ALWAYS tuck in girl.

    I love my boots too much to hide 'em away.

  • ranksubjugation

    Yeah, I pretty much stick with opaque tights under dresses. I would like to try skinnies/jeggings, but I always die a little bit inside when I see those on me in the dressing room, so I never buy. Maybe I should go skinny jeans shopping while wearing my boots…

  • Serena from Style on a String

    I agree with everything you said

    I have jeans specifically for tucking into boots because I ADORE the look

    Dark, straight-legged jeans that are NOT skin tight or skinny

    And I have another pair of slightly wider straight-leggeds that kind of work to be tucked into my boots but not really

    The extra fabric is awful and it stretches out your boots a bit :\

    Style on a String ..because style has nothing to do with money.

  • Make Do Style

    I love tucking my skinny jeans into boots although sometimes with my flat thigh high black boots I feel a bit of a storm trooper!

  • Kaija

    Not a fan of the skinny jeans and don't really want to spend $ on jeans I don't really love/will go out of style within a year or two…so I tuck my straight jeans or wear thick leggings, as other commenters have suggested.

    For tucking non-skinny jeans, I recommend a pair of cute knee socks with lots of elastic to them. That way you can wrap the extra jean tightly around your calf and ankle and pull the sock up and over it to keep it in place. And you have the option of leaving a little bit of the sock showing at the top of the boot, which can be fun (colors!) and add to the layering :)

  • Mrs.M in MI

    I just started tucking my jeans into my boots this fall. I carry my weight in my thighs so I was very afraid of bringing attention to my least-slim area.

    My solution is to wear very dark jeans with my light tan vintage western-style boots. The dark jeans recede and the light boots take the spotlight so I feel balanced.

    I prefer to wear bright or light tops that are pretty body-conscious and have a hem on my low hip with this ensemble. It shows plenty of leg and keeps a slim line all the way to my knees.

  • Healthy and Homemade

    Great post Sal! I almost always tuck my jeans into my boots because it helps balance out my top half. I pretty much wont wear skinny jeans if I'm not wearing boots, because I feel like an ice cream cone. For ankle boots, I wont tuck my jeans in, but leggings look cute with ankle boots. Man, I WISH I had jeggings =P They're always sold out at Target.

    Here's a tip for keeping your pants tucked in: Fold up the bottom part of your jeans into a big cuff, and then take knee high *or mid-calf* tight fitting socks and pull the socks over the bottoms of your pants. You can either let the top of the sock show just above the boot, or you can scrunch it down. This definitely helps keep the pants pulled downward, and there's no bunching around your heels either =D

    This works mainly for "straight leg" but not super skinny jeans. For super skinnies, they stay in place all on their own, woot woot.

  • Meli22

    lol at husband mike…

    I loved that tidbit of dark jeans and light boots to balance a prominant thigh Mrs. M! I have a friend who can't do this look for that reason- her calves and legs are tiny compared to her body! She wears lighter wash jeans and black boots, but she can't tuck them in because it draws attention to the small bottom and larger upper half… she needs to reverse it! I never did figure out why it didn't work right- now I do! :)


    Love this look…as long as no Uggs*
    Keep those for the country side travels I think… Great new week Sal! xo*

  • lisa

    Great tips in this post, Sal! Skinny jeans in a dark wash tucked into tall flat black boots is one of my go-to uniforms during winter.

  • Hanako66

    great post, I think you nailed it!

  • Rebecca

    I have a very bodacious, ample, curvy ass, and some thick thighs, and I love to tuck my dark skinnies into my light brown western boots. And no tunics, my ass looks hot!

  • L.A. Daze

    A tip from somebody who has been riding horses her whole entire life (and as such, has to wear those annoyingly tall, super tight, field boots). Get a good pair of tall socks, slide them over your jeans, and it's much easier to get a streamlined look in your boot. No awkward bunching, and the boots are easier to pull on/off. Even with zippered boots, this makes things much easier.

  • Clare

    Great post, Sal! It took me YEARS to figure out what the heck I was doing when I tucked in my jeans, but now I do it constantly. A couple of tips for keeping pants from bunching or moving around too much in the boot:

    1-tuck the pants into a heavier gym sock first. The socks will keep the jeans in place better than just the boot. Make sure the boots are big enough to wear with thicker socks, and don't try this with anything wider than an ankle-leg pant; TOO MUCH bunching!

    2-invest in those pant harness thingys. I bought pant clips on ebay last year and wear them almost every time I tuck, especially with slightly wider jeans. I think they're mostly sold to equestrian-types, but mine set me back a whopping $7 and were TOTALLY priceless.

  • Rosie Unknown

    I love tucking things into my boots, but I want to get new pair of boots: just below knee length, with higher heels.

    Great post!

  • La Historiadora de Moda

    This is a fantastic post! I'm really glad to read that you don't think this style is the domain of thin women only. Because of my curves I used to be terrified of this style, but living in Europe and seeing so many women of all shapes rock the skinny jeans, I got over the fear. I also tend to cuff my skinny jeans and pull socks over them when I wear them with boots. I should probably watch the proportions a bit more than I do, though, to streamline my look.

  • enc

    Though I am not a cowboy-boot tucker myself, I find this example to be very sweet and effective. I love tucking pants into boots so the shaft shows. It's just plain cool.

  • Pat

    I agree with everything you said but I want to add another idea noone has mentioned yet.

    I'm quite partial to the loose (think cargo/combat pants) that are tucked in, though I've never done it myself. I think I'm too old for that!

  • Anonymous

    I just recently jumped on the skinny jeans tucked into boots bandwagon. Found a super affordable and comfortable pair of skinny but not skin tight jeans at JCP, the A.n.a curvy fit jeans. Though I have to agree the leggings version is more comfy. Both worn with long tunic is my preference.

    Commenting on another post of white being hot in India, I hail from there. Unfortunately certain things portrayed about India by media is not true however I agree on this one. Fairer skin is preferred. Now it is sad to hear that it has affected the job market as well. When I came here and heard of skin tanning I couldn't help but chuckle. People seem to want what they don't have instead of being comfortable in their own skins which is what Sal so much tries to emphasize in this blog.

  • Audi

    I love the look of tucked in jeans, although unless they're tucked into those wide-mouthed cowboy boots I rarely get through the day without having to re-adjust the bunched-up fabric around my ankles at least once. Leggings are much more comfy, to be sure.

  • Anonymous

    I so wish I could rock this trend. But since I can hardly find boots that fit over my calves, much less over my calves PLUS jeans, I think I'm out of luck. (My heavy thighs don't help things either).

    Oh well. I'll just have to live vicariously through all of the ladies on here who do rock this look!

  • Winona

    Fabulous post, Sal! I really like that you use bloggers as examples–it makes your posts even more accessible and adorable!

  • rb

    hey Michael.
    I think my dad invented that look. He usually had one whole pant leg loosely tucked into one (but only one) cowboy boot. I didn't know it was high fashion. When I was in high school and he went around like that in public it made me want to DIE!

  • scrapbook

    nice post 😀 – very informative, xx

  • The Man Who Knew Too Much

    I like the pants in boots!

  • Nadine

    I never liked jeans tucked into pants… it always reminded me of horses and riding ;)… but some girls look really good wearing it.

  • Elissa

    I just found these, which would be helpful or the tucking/bunching issue. But like bulky shapewear, these are functional but mortifying if somehow revealed. In other words, take your boots off in private.

  • Lemondrop Marie

    What helpful tips- I am totally printing this post and hanging in my closet.
    I would also resemble a dwarf at some point in thick tucked in denim. Still laughing at the fab simile there…
    Marie @ Lemondrop ViNtAge

  • Iva

    great tutorial!..and that puppy is adorable!

  • chic

    Yay!! I'm so flattered, thanks for featuring me and my cute pup that was on loan that week :) I wish I were still dog-sitting… sigh…

    As for the boot-tuck issue, I am a true believer. I find that it makes a casual jean outfit a bit edgier and that it's really practical when you live in a rainy city, like I do now. No more soggy pant leg slowly creeping upwards.


  • Imogen Lamport, AICI CIP

    Tucking works best with a slim or skinny jean.

    If you're hip conscious, then wear a tunic over your jeans and voila – gorgeousness!

  • Missa

    I'm a tucker. I like to do the knee socks over the skinnies too with some sticking out over the top of the boot sometimes. It also helps with the scrunching.

    I do tend to go with a tunic style top usually because the skinnies that I have are old and a little too low-rise for my current liking.

  • Moomby

    great post! thanks so much for sharing!

  • Work With What You’ve Got

    Oh my gah. I feel famous. I wondered where all those new readers were coming from!~ Thank Sal!

  • Mademoiselle Frou-Frou

    ever since i bought a pair of jeggings, i am LOVING wearing my boots with jeans. otherwise it's a bit uncomfortable to try and tuck my jeans.

  • WendyB

    Wait, did I miss the post on putting on pants one leg at a time? START FROM THE BEGINNING, FOR GOD'S SAKE!

  • Courtney

    I have 4’11” curvy thick legs and butt. Love the feel of the Hollister yoga pants but, don’t own any. Tired of off brand cheap material does anyone suggest a particular brand for low rise leggings I can put into Uggs or Fashion not quite knee high fringesy boots or cowboy boots? & jeans I love the fit of Lucky & Cruel Girl but I have no skinny jeans with a low rise petite for curvy need suggestions… Thank You:)

  • Slim boots

    Yaa !!! I like your style of tucking pants inside the boots, they look more beautiful for wide calf boots as well.