Reader Request: Modernizing Boot Cut Jeans

How to wear boot cut jeans

Anne had this great request:

So, I’ve tried the skinny jeans – they’re not all that great on me. Boyfriend jeans make me look kind of stumpy. Boot legs jeans are really the best fit for me but they’ve been around for quite a while. How do you make them look fresh?

I believe I own a pair of boot cuts, but they aren’t exactly my go-to. I do denim bottoms but they’re frequently stand-ins for leggings and therefore skin-tight and paired with tunics. I firmly believe that boot cuts are a classic style, great on many figures, and well worth wearing despite skinnies being more prevalent. But I’m going to have to look to my blogging friends for some contemporary bootcut inspiration.

Before we dig into the photos and tips, though, a quick note about the style itself. Boot cut jeans have been recommended by stylists since the dawn of styling, and with good reason. They make most women appear tall and/or long-legged, and the slight flare at the hem balances figure volume. Boot cuts are not to be confused with flares, which have a much larger opening at the hem and read a bit more like bell-bottoms. Especially now, after years of refinement, boot cuts are relatively slim in the leg and feature a minimally noticeable flare at the ankle.

In my opinion, unadorned, dark-wash jeans of ANY style are always a good bet, and that goes for boot cuts, too. Dark washes are classic, clean, and much easier to dress up or down than destroyed, light, or heavily detailed washes.

Now, let’s dig into Anne’s question. How exactly can you modernize a pair of bootcut jeans?

Go fancy

Maegan, … Love Maegan

Jeans are the classic go-to for casual and weekend wear. Doing your bootcuts with a sweatshirt and sneaks won’t do anything for them (or you) in the way of modernization, since that combination of pieces is expected and common. Choosing structured, ladylike, or fancy garments and accessories will create fun juxtaposition and also update your overall look. Sleek blazers, long strands of pearls, brooches, structured handbags, stacks of bracelets, killer heels, on-trend ballet flats, and diaphanous blouses all provide a bit of fanciness to balance the naturally casual vibe of the jeans. (For more jeans-related fabulousness, check out Love Maegan’s 30 Days 30 Ways: Jeans and a White Tee Challenge. And yes, it could be argued that Maegan is wearing flares here, but the outfit itself would work equally well with bootcuts.)

Go trendy

Alison, Wardrobe Oxygen

Now, see here! “Go trendy” doesn’t mean “force yourself into a peplum blouse and LIKE IT.” Trends encompass patterns, colors, and fabrics in addition to cuts, lengths, and garment types. Since bootcut jeans are a classic piece but can sometimes feel a bit dated in this world of skinnies and boyfriends, pairing them with tops, accessories, and shoes that seem very of-the-moment will create balance. Don’t pick a trend that clashes with your personal style. Seek something that appeals to your eye and your aesthetic sense, but still aligns with the season’s hot items.

Here, Alison has boldly chosen to do a poncho with her bootcuts. I say, “boldly” because if the poncho were crafted from brown and orange acrylic yarn and the jeans were pale, stonewashed flares she’d have given off a very Woodstock vibe. But the poncho is chic and updated, classic black and perfectly on-trend. Her bootcut jeans are a dark wash, and create a fabulous balance against the drape of the top.  (Also be sure to check out Alison’s response to reader question about bootcut jeans back in 2007!)

Go funky

Lisa, Respect the Shoes

Trendy and funky can have a lot of overlap, and Lisa’s sequined pullover could fall into either category. But the idea here is to steer clear of the plain, the expected, the normal, and reach for items with flair and interest. If it works for your figure, try a tunic-length top, or assemble some interesting layers that fall at different spot along your torso. Opt for outrageous platform shoes, a conversation-starting necklace, or a highly embellished blouse. Again, when we think bootcut jeans we think “casual weekend staple.” Pairing them with personality-laden tops and accessories will help update your look.

Top image courtesy Gap

**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 2012-07-12 06:20:51.

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30 Responses to “Reader Request: Modernizing Boot Cut Jeans”

  1. katesome

    Oh my goodness!!! I almost cheered when I saw this post!

    Warning: I am jeans obsessed.

    I have an ‘apple’ shaped body. I’m 6ft, long legs, I carry my weight around my middle, big boobs and I am plus sized. I have no butt to speak of and I don’t wear heels, it’s frightening enough the whole 6ft thing.

    I look OK in skinny jeans, but I always need to wear heels or I just look out of proportion and all the focus goes to my tummy so I feel like there are only a few tops I like with skinny jeans. I hate wearing heels and I just don’t want to squeeze myself into skinny jeans all the time.

    I live in Australia and currently, there are NO plus tall bootleg jeans in the country. NONE. NONE people!!! 🙁

    I truly think we will look back on the 20teens as the years most women looked out of proportion and uncomfortable in their clothes. Oh, and half of them were falling over in their heels all the time.

    I have resorted to making my own pants, I sew a fair bit so not too hard. I made the first pair flares and I love them. I recently spent 2 weeks in Manhattan and I can tell you, the most cutting edge stylish people I saw were wearing flares. Skinny just aren’t interesting and cutting edge anymore.

    How else to do stand out and make a statement if everyone is wearing skinny? Flare/bootleg is coming back. I spoke to a number of high end fashion stores on Madison Ave who were all saying the same thing. In fact asking me who I was wearing!?

    I say, wear them however you like, the photos above show they are just as, if not MORE versatile than skinny jeans.



  2. Patti @ NotDeadYet Style

    I love these tips surrounded by pictures of some of my favorite bloggers! Alas, I just wear my bootcut jeans with boots and tees most of the time, although I do try to keep the boots fabulous. And I still *prefer* my straights, but I agree with you that any simple dark wash jean is pretty much a classic now.

  3. Jen

    Love this post! I work in a Junior High/High School and every Friday we have “spirit day” where the faculty come dressed to work in school colors and jeans. While sometimes I will wear my skinnies with a black tunic (our colors are orange, black and white), I hesitate to wear skinnies without them being part of a long over lean look around my adolescent boys:). So most Fridays it is the boot cut for me. I am the odd duck among my fellow faculty though, as often I’m not wearing sweatshirts or polos, but more fashionable tops in the colors of our team. I’ll have to try some of these looks come fall! Thanks!

  4. Kate K

    Yes! …Love Maegan is one of my favorite bloggers because she makes wearing jeans look like an art form. I too struggle with the skinny jean phenomenon–I’m always working SO HARD to balance out my hips and thighs and flatter my tummy that it’s just exhausting. Bootcuts are just a better option for me but I do feel somewhat dated (or mom-like.) These are great suggestions Sal!

  5. Aimee C

    I don’t even try to change what ain’t broke. I put on some tough-looking boots with my boot cut jeans and a cute top.

  6. Cynthia

    I always love to wear bootcut jeans. My favorites are from AG. I don’t particularly feel like they look dated — they’re dark wash, and they’re very slim cut in the upper leg (the Angel style) and I’ve never even considered that they might be out of fashion because they make my butt look fabulous. Never would I have imagined that I’d say “paying that much for jeans is worth it”, but paying that much for jeans is worth it.

  7. Anne

    Hey Sally, what a fun surprise to see my question posted! Thank you. These tips look great, will continue to check in to see what other pearls your readers cast out. Have a great day.

  8. D

    Oooh I love bootcut jeans. I’ve made peace with skinnies now that I’ve found a pair that actually fits my booty and legs, but bootcut will always be my favorite. I like adding heels (that might be because I’m mighty short) or a blazer or a silk blouse to dress my bootcut jeans up.

  9. Bootycut

    I love bootcuts too. I sort of think of them as just jeans, normal jeans. Basic jeans. Skinny jeans just don’t work on me, at all.

  10. Keilexandra

    I’m petite with short legs (5’2.5″ but only 29″ inseam) and I hate wearing heels, so I’ve embraced the skinny trend because it’s the only way I can buy full-length pants that don’t need to be hemmed. My favorite pair of bootcuts are really old, the Zelda Barely Boot fit from Express, and sadly that style has been discontinued.

    Sal–if you catch this, I’d love to see an Insomniac picks post on slim-fitting (think BR Sloan fit or AT Modern fit) low-rise bootcuts. I’m willing to hem now, if I can find a non-petite pair that is cut slim through the hips with a low enough rise (7-7.5″).

  11. Heather

    Trouser jeans and wide leg jeans work best for my body, so that’s what I wear. My legs taper dramatically at the ankles, it is not flattering to emphasize that. I do own one pair of jeggings, but they get worn under LONG tunics with boots only!

  12. Audrey

    I’ve always been a fun of boot cut jeans. But getting a pair these days is so hard. I’d style them with feminine tops or a blazer and flats or wedges. Great post!

  13. The Waves

    I’ve been into flares for a while now, but bootcuts seem a little more… sophisticated, perhaps? If I had a pair of bootcuts (sadly I don’t) I’d probably wear them the same way I’ve been wearing flares – with a menswear-inspired, sharp tucked-in shirt, a belt, and brogues or loafers.

  14. Stacy

    I wear bootcut jeans or jeans with a slightly bigger flare all the time. I’ve tried and tried to wear skinnies, and they just don’t work on me.

    I often pair my jeans with a camisole and shrunken cardigan in funky colors, with some fabulous wedge heels. I also like to go Maegan’s route, and wear something ultra feminine and lacy with a classic pearl necklace and more traditional pumps. Another look is a fitted, long-sleeve top in a fun color tucked in with a funky belt and funky boots.

    And I fully agree with Sal’s comments on dark, solid washes without “whiskering” or distressing.

  15. Mrs.M in MI

    Yes, I do own a pair of skinny jeans that fit me well, and I have mustered the courage to wear them as pants and not leggings, but bootcut jeans just look so much better on me.

    As for how I wear them, it’s a matter of proportion. If I’m going to wear skinny jeans, then I’m going to wear looser, longer tops. If I’m wearing the volume on the bottom, then I’ll wear tighter, shorter tops. Generally it’s the same type of items – tees and cardigans or collared shirts and sweaters. I only wear jeans for bumming around so it’s all really casual.

    I actually picked up my last pair of bootcuts at the Salvation Army. Since they aren’t the coolest anymore, the thrift stores are lousy with ’em!

  16. Heather

    I must admit, I’ve done the “french roll” that was popular last when I was in middle school with my bootcuts a few times lately with irony (they were dragging on the floor and it was bugging me), yet I got several compliments on it!

  17. Sonja

    As many other commenters, I usually don’t wear skinnies either, although I’ve bought a pair to wear with boots in the winter. My other jeans are all bootcut, I totally love the style and would never have thought of it as “dated”.
    I normally try the “go fancy”-route – it’s not “very fancy” in my case, but I think that just pairing these jeans with any kind of heels looks fabulous instantly.
    If it’s not heels, it’s often the “common” way, as Sal put it, with sneakers and a tee. But I try to keep it polished and classic by wearing a flattering, fitted tee or sweater in a solid colour and with a low neckline, and also chucks or another kind of old school-sneakers.
    Oh, one last thing – if I want to wear flats with my bootcut jeans, somehow I always reach for a pair with a slightly pointed toe, they seem to look nicer peeking out than a rounded cap. But maybe that’s just me.

  18. Mary

    I am all in favor of whatever makes any of us feel like a million bucks!
    I still own a pair or two of bootcut jeans — but even before skinnies came on the scene, I didn’t love wearing the bootcut style.
    For the past ten years, I’ve tapered my jeans (and work & suit trousers) down to a straight leg. I like the look, but more importantly (for me) I love the feel of a pant leg that fits closer to me.
    I have a “thing” about my clothes hanging off of me — I don’t like bows or string ties or sashes or fringe or long necklaces. And my body translates wide-legs, flares, and even bootcuts to “that’s swinging way too far away from my body when I move!”
    So my preference for straight-legs and skinnies doesn’t have anything to do with the look so much as it’s just a weird quirk of mine.
    Oh yes — and Sal’s right, the darkest wash I can find wins every time!

  19. Martina

    I believe that the most important with pants is length, rather than style!.
    Right now, I fell that shorter lengths (that leave part of the ankle exposed) look more modern and edgy than the floor sweeping styles that were popular a few years ago. Of course how short you’ll actually go depends on the style: skinny jeans can be much shorter than, say, a bootcut of a flare. But a small trim did wonders on all of my thrifted goods!

  20. Lydia

    I love bootcut jeans, and always have a pair or two, or three, or four… I did buy a jegging skinny jean, and like it as well, but for some reason, I feel classic in the bootcut!

    I wear mine with sheer ruffle tops over camis, and really vivid or patterned and unusual tops, and often wear a jacket — even a structured hoodie style or ponte (I guess) type jacked. I wear them with cardigans long and short, and love to layer bootcuts. I have bootcuts shortened to wear with flats, as well as heel length.

    For those who find bootcuts hard to track down, I recommend NewLook (from the UK) jeans as they ship internationally fairly fast. They are not the greatest quality, but I like the thinner material, and they come in a huge range of sizes, as well as three different lengths. The Gap bootcuts are great too, but sizing and cuts keep shifing.

  21. Heather

    Great Question! My biggest,problem with boot cut jeans is that they have to be long to look good and they have to be hemmed to fall just right with heels to look the best. My last pair bit the dust last week when I made them into cutoffs. I’ll need another pair before I can work on modernizing the look!

  22. Osprey

    Ooh I love my bootcuts. I like them in a lighter wash and I’m afraid I often pair them with sandals and a loose blouse.So dated, it’s already back in style! Right, right? :/
    These new tips are very helpful, although dark-wash bootcuts still remind me of Oprah and her “let’s make over the stay-at-home moms of middle america” shows.

  23. Angela

    I don’t own any boot cut jeans. They just don’t appeal to me right now. I rarely wear denim, but for when I do, I have two pairs of skinnies, one pair of trouser jeans, and one pair of flares.

  24. Katie

    My main tip is even if the legs are loose,make sure the waist/butt is tight. I thought I hated boot cut for a long time, but it’s just that my butt is nonexistent and when the pants were falling off me, they look gross. But when they’re a good fit, they look sleek and trendy again.

  25. Beth

    Hi there…I LOVE the boot cut jeans you show in the very first picture..they are just the jeans…Do you remember which brand/style they are? GREAT post..thanks!