Are tall boots over skinny jeans back?? This is such a polarizing topic. As evidenced by the responses to our IG story last week (asking this very question), 60% said yes, 40% said no, and our inbox was promptly flooded with DMs from readers saying either a) tall boots over skinnies never left, or b) tall boots and skinnies are dead, gone and buried.

I get it — I’ve been all ankle boots and over-the-knee for a really, really long time.

So when did tall boots over skinny jeans actually die? We’re not exactly sure…but it looks like somewhere around 2013? 2014? Tall boots started creeping back into favor recently, however, as midi dresses (and skirts) gained in popularity. Know what goes amazingly well with a midi? TALL BOOTS.

But I want to talk about tall boots over jeans. The way we wore this look the first time around (pre-2014) still feels…dated. Remember the look? Tall, flat riding boots — usually in a solid brown or black, rounded toe — with skinny jeans and some sort of long sweater, that was the uniform  Truthfully, many of us are not ready to go there again. And yet…there have been a few (recent!!) instances where tall boots over skinny jeans made me swoon.

What makes the difference?

Well…we’ve been debating this, over here at The Mom Edit office. And after much discussion, we came up with a few guidelines (for lack of a better word) to rock tall boots with skinnies…as well as some advice on picking a tall boot that will feel fresh.

The New Rules For Wearing Tall Boots Over Skinny Jeans

1. Tall Statement Boots Are A Sure Bet (Especially Snakeskin)

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

sweater (sustainable!) (xs) | jeans are sold out – here are the same jeans, different wash (25) – plus size option here (sustainable!) | boots (old, few sizes left) – or try the same pair in this season’s colors | bag (sold out – try this one)

I picked up a pair of these brightly colored, tall snakeskin boots during the holidays last year. I initially wore them with skirts (think: a dramatic ball gown skirt – see the outfit here)…but I found, in the freezing winter temps — that these boots were such a statement that they even felt fresh over skinny jeans!

My snakeskin boots are from last season, but they’ve been released again, with new colors. You can find my current favorites in last week’s article: Sweaters, Jeans & Tall Statement Boots: My New Go-To Party Uniform.

But I’m not the only one loving tall snakeskin boots with jeans. Reformation (whose styling I adore) recently showcased their recycled cashmere sweater by styling it with skinny jeans and tall snakeskin boots, too.

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

2. Try The New Neutral: Taupe

Instead of those old brown riding boots…try lightening up. Taupe (or beige or even white) definitely looks fresher. It’s part of the giant white sneaker phenomenon, but much easier to wear.

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

tee (xs) – plus size option here | jeans (25) – plus size option here (sustainable!) | boots | bag (sold out – try this one)

3. Choose A Tall Boot With a Heel…And a Pointy Toe

I keep trying to find a tall, flat boot that I’d be willing to wear over jeans. Aaaaaand…I’m still lookin’. But sexy tall boots — the ones with a bit of a heel, a pointed toe — these boots I love over skinnies.

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

 jeans (25) – plus size option here (sustainable!) | boots | bag (sold out – try this one)

4.  Look For a Lower-Shaft Boot…With Some Slouch

The neutral boots I’m wearing above are a few inches lower than traditional knee-high boots, which is yet another reason that they look fresh. Take this up a notch by finding a tall-ish or mid-calf boot with some slouch. Both Free People and Shopbop have a perfect examples of this:

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

black boots (Free People) | tan boots (Shopbop)

5. Stick With High-Rise Jeans (And Tuck In That Top!)

I suspect there’s a long, slouchy sweater somewhere that I *could* wear with my updated tall boots and skinny jeans…but it would require a half-tuck (to show off that waist) in order to keep the look current. A much safer bet, for sure, is go all in on the high-rise.  High-rise skinnies and a tucked-in top is the easiest way to make your tall boots feel modern and fresh.

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

Are tall boots over skinny jeans in? Such a polarizing topic. When did tall boots over skinny jeans really die? We want to talk about tall boots over jeans.

Outfit 1:tee (xs) – plus size option here | jeans (25) – plus size option here (sustainable!) | boots | bag (sold out – try this one)

Outfit 2:sweater (sustainable!) (xs) | jeans are sold out – here are the same jeans, different wash (25) – plus size option here (sustainable!) | boots (old, few sizes left) – or try the same pair in this season’s colors | bag (sold out – try this one)

Shop The Best Tall Boots To Wear Over Jeans

A bunch of these are selling out, so I linked a few to multiple retailers, in case finding sizes is an issue.

xo,

S

38 COMMENTS

  1. I needed to read this! I have very limited closet space and much of it is taken up by tall boots that I never wear. For all the reasons you outlined above. I am finally going to take them out and donate them. Much more room for all of the booties I have purchased this fall. Still have to ponder the tall boot scenarios you described.

  2. Apparently I missed the memo that tall boots over skinny jeans wa old and tired. I am just hoping my brown tall boots don’t look too wide after losing some weight. Would hate to get rid of them. Not sure what to do otherwise but those and the Gentle Souls Moto boots are great. Guess I will just be out of style! 🙂

  3. @Kari, I’m with you! If tall boots and skinny jeans (with a sweater untucked) are out and dresses over turtlenecks are in then I guess I’m okay with being out of style from now on!

  4. I just wear what I think looks cute, and I think round toe boots are cute just by humble opinion. I wish the clothing designers would finally get rid of those fake wrinkle lines in the top of the jeans by the zipper lol.

  5. I agree with the tall boots over jeans looks dated camp. But they still look great with midis that are so hot right now. I think booties with skinnies looks much more now. Just personal opinion though, right?

  6. I’m short with chunky thighs, so this is a look I’m sitting out. However, the riding boot/skinny jean look never left Minnesota preppy moms, I see it every fall will a sweater/shirt/puffer vest/Barbour-type jacket.

  7. I agree that look is out though I’m still sad to see it go. It’s not awful just a little dated. I think there was a post a year or two ago about mid height boots and skinny jeans- would love to see an update to that! I wish I could get into this sweater tucked into high waist jeans thing. I like the look but it’s not comfortable to me and I’m a baby about comfort. I can handle it with thinner shirts but sweaters are just too much bulk to tuck in. I don’t have that much extra room at my waist 🙂

    • I’ve been hunting for sweaters that tucked easily…and the gray Reformation one I’m wearing is one of my favs. Warm, but nice and thin and tuckable.

  8. I’m wearing my tall brown boots over skinnies right now. But whatever, I like them. I have big feet and skinny legs, so my tall boots balance all that out. Don’t get me wrong, I like my short boots too, but with my big feet I need to have heels with my short boots to look right, and mama doesn’t want to wear heels every day, especially considering how much I walk at work. So tall, flat boots for the win. And they’re warm. I’m going right from work today to my daughter’s tennis match, and it’s going to be in the 40s, another win for the tall boots!

  9. But boots are so expensive 🙁 who has $1000 to tweak the toe/heel/shaft of their boot collection every season? Can you do a piece on timeless boots for those of us who try to build a wardrobe that doesn’t have to be discarded and replaced every few years?

    • Timeless is going to depend on your personal style. If you’re really preppy, timeless might be classic riding boots. I could easily argue that combat boots are timeless (those go much more with my style than the riding boots), and I’ve been wearing similar classic Sorel winter boots since I was 6. Timeless. Personally, I plan on keeping my colorful snakeskin boots around for a while because I LOVE them. Timeless has a lot to do with pieces that make YOUR heart beat fast.

  10. Super timely post. While I still like my skinnies and ankle boots, I have been feeling a little unsettled with the look- kind of how I felt several years ago with the tall boot/ skinny jeans uniform. I’ve been changing up my jeans style- flare/ high waist/ slouchy boyfriend/ cropped wide. I’ve even been looking at low slung pants with a more dropped crotch ( kind of Nili Lotan-esque). Even with all this style soul searching- it NEVER occurred to me that maybe tall boots ( with some tweaks) over my skinnies could look fresh. Hmmm. Something to ponder…

    • Girl, I am SO with you on this comment. It’s like I have a multiple denim personality disorder right now. But I keep coming back to my skinnies because they still look the best with sneakers….so….(I mean, I walk A LOT). A high waist helps, for sure.

  11. These trend articles TME does are so interesting and helpful. I was wondering last year if these were “out”. While I don’t follow trends religiously, I make subtle updates. Yes, my bootie collection far outnumbers my tall boots. I feel like tall boots are such an investment in money and space! Also, can you give any tips on pointed toes for shoes, boots, etc. They look amazing, but ouch! Maybe some are less painful than others.

    I love y’alls style b/c each of you offers different perspectives and price points. I feel like you promote a lot of quality brands too. Thanks for all you post! Big fan!!!

    • Thank you!!! In terms of comfort…I prefer a slightly pointed toe (like the boots featured) rather than the really looooong pointed toe. I also tend to buy my boots big enough so I can wear thick wool socks underneath them – that’s really my favorite thing about wearing boots, actually: THICK SOCKS. So while I’ve sometimes found boots uncomfortable, it usually has to do with the height of the heel rather than the pointed toe.

  12. I agree with some of the other posters… quality tall boots are an investment and to me tall, flat (riding) boots can be a timeless piece. Especially for those that are looking at sustainable wardrobes that don’t have to be overhauled when trends die. The pictured statement boots on the other one are more likely to feel dated as the fad wears off. As a petite woman with very, very skinny legs, finding a pair of well fitting tall boots has been a challenge to begin with, those look like they’d swallow me whole (like I’m playing dress up in my mom’s closet… )

    • I totally get what you’re saying here. What is really comes down to, I think, is one’s personal style. For me, the timeless boots you describe have never been my thing. Even when tall boots over jeans were at the height of popularity…I still didn’t wear riding boots. I totally respect that MANY people love them, but preppy style in general, is not my aesthetic. I’ve always gravitated to a statement boot, and snakeskin boots are something that I CAN see myself wearing for years and years. That have that sort of punch of impact that looks good with all of my black sweaters (haha), and are amazing peeking out from under skirts. I especially like snakeskin in the colorful prints, rather than anything that looks real. These boots go beyond trends and speak more to my personal style. Trends just will influence what pieces I style these boots with, rather than answering if I’ll wear them or not. Does that make sense?

  13. I have noticed tall boots coming back into style and love how they look with dresses especially. Unfortunately muscular legs make it almost impossible to jump on this trend…I have never been able to find a tall pair of boots that fit my calves without cutting off circulation. “Wide calf” boots exist, but they are usually cut oddly j(like too wide in the ankle)…I wish someone could figure this out!

  14. Who would’ve thought an article on snakeskin boots could get me thinking so deeply? After reading this, I realize my personal style is more classic/preppy than I thought. I’m trying to choose pieces that will stay the course, so thank you for helping me. With that said, I’d love to see a post on how to style classic riding boots in a new way. @Shana, maybe not your thing. But, anyone else at The Mom Edit? I’m talking a fresh take here. Not riding boots and skinny jeans.

  15. I just bought tall beige suede western inspired boots yesterday, I was thinking I would return them even though they are super comfy. I am 47 and by now I should just wear what I like and looks good on me, even if its not exactly on trend. From your post, it seems like maybe I will keep em and rock em!

  16. Putting a plug in for LD Tuttle ‘The Lost’ boots as tall, timeless boots. They are my holy grail of chic, effortless, comfortable. They are a splurge, but I wear them all the time. When I saw them, I knew I had to haft them. I did find them on sale at ShopBop two years ago. They are released every year, though, so not currently on sale.

  17. Good stuff S! I’m going to try my slouchy suede boots with skinnies! Love your statement boots, but not in the budget this year! Awesome pics of you btw!

  18. I actually always thought the Weitzman OTK boots have that same aesthetic as riding boots. Comes to show how we interpret the same thing differently, these posts of you with those suede fitted boots, feel similar to me, so I guess I was not differentiating between OTK and riding boot — both fit the category of timeless and investment pieces.

    https://themomedit.com/the-best-shoes-and-boots-from-the-2018-nordstrom-anniversary-sale/

    https://themomedit.com/the-best-bags-and-boots-to-gift/

    And yes, your personal style can ignore trends completely, but since this whole post was about what is ON trend now and how to change things up to be current, the tall snakeskin boots are supposed to represent that here, isn’t that right?

    I guess we don’t always have to agree on all posts. I prefer the sustainability angle, but others might find this speaks to their style long-term or willingness to spend on a current, on-trend item.

  19. @lala – I’ve got athletic legs as well, so tall boots were never up my alley. I’ve never liked the look of tall boots, especially with jeans tucked in. However, I do think over-the-knee boots are ideal for thicker calves. Far more comfortable and look wonderful with midi skirts, etc. I mean, with midi skirts, you can’t tell if the boot is over or under the knee! (I still don’t like boots tucked into jeans though!).

    As far as the knee high snakeskin boots, cute but not timeless. Let’s talk again in 6-12 months and see if anyone is still wearing them.

  20. Tall boots over skinny jeans have never been my thing, (I think it’s a really uncomfortable combination) but I really love what your saying here about personal style and trends. Also, combat boots forever!!! 😉

  21. Tall boots over skinny jeans still looks a little dated to me right now, but I’m sure we’ll all come around, just like we did on ankle boots and skinnies the first time around. I think it’s a nice look.

    I’m ready to move on from shirts (and now chunky sweaters! yeesh) tucked into high-waisted jeans. Time to admit that it’s (1) uncomfortable and (2) unflattering on anyone with abdominal fat. Who’s with me?? P.S. bodysuits are an abomination, don’t try to tell me that’s the answer to my tucking problems

  22. To me there’s really no such thing as “timeless” – trends change and things that were popular at one time will always look dated 5-10 years later. Sometimes things come back “in,” but it’s usually in a way that is just different enough to make your old pieces unusable (see…this article).

    IMO, the only way to avoid updating your wardrobe all the time is to stick to well-made basics (true basics, like a black pencil skirt or a wool peacoat) and not chase trends. But that’s not much fun (at least not compared to neon snakeskin boots!).

    • So these comments are giving me….IDEAS. Wouldn’t it be interesting if….hmmmm…if we somehow could recommend a set of timeless pieces based on someone’s personal style? For example (and this one is easy), if your style is preppy, I’d likely recommend cashmere twin sets, tall boots, and maybe some sort of plaid shirt? But if your style was, say, Kate Moss 1994, I’d recommend a strappy slip dress, some sort of statement coat, and probably…a white t-shirt? IDK – I’m just thinking off the cuff here. It’s hard to properly define “types” – we’re all so much more wonderfully complicated than that, but it might be fun to at least start with a few of the contributors? And maybe ask what are our most timeless pieces? See if there’s some sort of pattern that emerges?

  23. Funny…I was just thinking that the over-the-knee boots I have been wearing the past few years (on those few Florida days that I can get away with them) were starting to feel a little past their prime. Was actually considering a pair of tall boots as an alternative. I imagine in another year or two they will feel fresh again. Perhaps I should just stick with my ankle booties a little while longer. Although those tall snakeskin boots are fabulous, when you live in a state where getting swallowed by an actual python is always a possibility, it’s best not to look like the victim on “When Animals Attack.”

  24. Yes, that would be great. There needs to be some way to divide out “timeless” from “tired” and tips on how to stay ontrend enough but still be sustainable and keep your anchor/investment/timeless pieces in play.

  25. That is a fun idea! Although my immediate reaction to “Kate moss 1994” is like…well isn’t that what’s trendy right now? We’re all wearing 90s jeans and stuff. I feel like someone who thinks their style is that right now might not think that in five years. Maybe broader categories like bohemian, sporty, minimalist, retro? And of course preppy.

  26. Here for this!!! It’s the Hepburn effect – maybe today you put Audrey”s little black turtleneck w destroyed denim or Kate”s trousers w Adidas – but their style baselines always resonate and adapt. I would LOVE. to see TME take on the “French five” approach to an autumn/winter wardrobe – what would you add and how would you mix those few pieces into your baselines?

  27. Thank you! I am not a particularly large person (5’2″, size 8) but I have never been able to find a pair of boots where it is not an absolute chore to wear over jeans. I have a pair of heeled, pointy taupe boots I purchased last year – but I think I will have to stick to wearing them with skirts and dresses…

  28. Yes! I would love to see more articles like this. I am always looking for the “holes” in my wardrobe. Plus I am a huge fan of French women style. Basically decide what looks good on you and wear that over and over again. I rarely jump on trends unless there is something I feel like I can wear for the next 5-10 years.
    If you do one of these articles please do a “personal” style of Carrie Bradshaw if she were a MOM. Would love to see that

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