Tall Boots?? The Best Way To Wear Them Now (Four Outfits)


One question that comes up whenever we talk boots is….tall boots:  In or out, S?  Are knee-high boots actually in….or out?

It’s a little tricky to answer.  On one hand, tall boots are classics.  But the whole boots-over-jeans-with-long-sweater thing?  We first introduced this as our go-to mom uniform….are you ready for this??…..almost ten years ago.  10.  TEN.  Ten years.  That’s a decade, you guys.  And yes – I do think it’s time to retire that overall look.

But….we all have these boots….just…sittin’ there….in our closets.  And yes:  they are classics.  So now our problem becomes how does one wear this classic style?  In 2017/2018?  When we’re not, obviously, riding our horses, clad in jodhpers, crops in hand?  #becauseclassic

My general answer?  We’ve gotta modernize the rest of our outfit.  And right now, the easiest way to modernize everything else around a pair of tall boots is seriously, crazy-fun:  Rock that 70’s vibe.

Whether we’re talking shearling coats, 70’s floral prints, or – my fav – midi wrap dresses, tall boots haven’t felt this fresh in years.

Knee-High Boots With Midi Dresses and Sweaters

This is my personal favorite – tall boots were made for this look.  The important piece here is the midi-length skirt – the top doesn’t matter nearly as much.  So pair your midi-skirt with a knotted tee, a cozy sweater (half-tucked or not), or go with a midi-dress.  It’s a feminine, fresh way to wear tall boots.

knee high boots outfitsknee high boots with midi skirttall boots with midi skirthow to wear knee high boots with dressesoutfits knee high bootsOutfit Details

dress: Plenty by Tracy Reece Aleah Dress (wearing a size xs) – I’m OBSESSED with this dress!!!  It comes in regular or petite sizes, and a ton of colors (including a mustard yellow I wish I had seen).  And happily….everything was just restocked at Anthro.  Here are a few favs:

boots: FRYE Renee Seamed Tall Boot – mine are actually vintage, but I swear it’s the exact same boot.  Frye’s are amazing like that.

bag: Rebecca Minkoff Mini Mission Bucket Bag – my exact color is sold out, but I think I like the tan-with-black trim (linked) even better.

sweater:  My sweater was from the Nordstrom Anni Sale and is now sold out, but this one is from the same line (also cashmere),  or try Free People’s giant turtleneck (so cozy!!) or this H&M Wool Blend Sweater (a brighter blue, but I LOVE the turtleneck)


Knee High Boots With 70’s Florals, Denim Minis, and Sherpa

Totally and completely obsessed with these tiny floral prints right now.  Add a denim mini and a sherpa coat and your tall boots look riiiiight at home.

how to wear tall bootswhat to wear with knee high boots going outmother denim sherpa coat

knee high boots outfit

Outfit Details

top: H&M Crinkled Chiffon Blouse (size 2 for reference)

skirt: the skirt I”m wearing is an old French Connection mini that’s almost sold out….but Madewell has basically the exact same thing.

boots: FRYE Renee Seamed Tall Boot – mine are actually vintage, but I swear it’s the exact same boot.  Frye’s are amazing like that.

bag: In a bizarre twist, my exact Coach Saddle Bag is only available in the UK?  Or in the good ‘ol USA without fringe, here.

coat: Mother Denim Sherpa Coat (xs for reference) – I love this coat SO MUCH.  It might even be the Buy Of The Year.  I wear it to school dropoff on the daily….which means that I wear it over workout leggings as well as regular stuff sometimes….and I wear it on date night.  It makes everything look amazing. It’s shockingly warm, without feeling super heavy….like a winter coat.

Aaand Finally:  Knee High Boots With Jeans (if you must)…

Truth be told, I think both of the below outfits would look better with a different boot.  BUT!  For the sake of argument!  I did want to try my hand at styling tall boots with jeans.  Especially since I hated all over this combo.  So.  Here’s what I came up with…..

…And Double Denim

Obsessed with double-denim in general, but especially with all of the interesting denim tops that are out right now.  Just enough of a 70’s vibe to work with tall boots.  (Am dying to try this with my OTK boots, tho.)

madewell denim tophow to wear knee high boots with jeansknee high boots with jeans

outfits knee high bootshow to wear tall boots

Outfit Details

top: Madewell Chambray Ruffle-Yoke Top (size xs for reference) – also dyyyying over this denim wrap top.  UGH SO COOL.  And since we’re here, there’s this swingy little number I would’ve died over post-partum.

jeans: Madewell High-Rise Skinnies – wearing a 25 for reference.

boots: FRYE Renee Seamed Tall Boot – mine are actually vintage, but I swear it’s the exact same boot.  Frye’s are amazing like that.

bag: Rebecca Minkoff Mini Mission Bucket Bag – my exact color is sold out, but I think I like the tan-with-black trim (linked) even better.


…At Least Switch To A High-Rise Jean

We need to talk about these jeans for a sec:  They. Are. Amazing. I threw them up on IG (@shanachristine) and got a ton of DMs from people who also swear by these jeans.  Including one of my 6ft tall friends.  Apparently Madewell has both tall and taller and voila!  Jeans for everyone.

I also love the suuuper high-rise and the buttons to reinforce the fact that you are, indeed, wearing suuuuper high-rise and fine, OK, put on your tall boots.  If you must.

high rise jeans with button fronttall boots with jeanshow to wear knee high boots with jeans

how to wear tall boots with jeans

Outfit Details

top: James Perse tee (size 1 for reference)

jeans: Madewell High-Rise Skinnies (size 25 for reference)

boots: FRYE Renee Seamed Tall Boot – mine are actually vintage, but I swear it’s the exact same boot.  Frye’s are amazing like that.

bag: Rebecca Minkoff

sunglasses: Tory Burch 


Sooooo…whaddya think?  Are you guys going to be digging your tall boots out anytime soon?  Other than the first outfit (with a midi dress), I probably won’t, but I totally get how practical they are.  Where are you on the tall boot spectrum:  yes, no…..sometimes?




  1. YES! I agree tall boots are a classic. I wore them with skirts for work all the time before we all wore them over skinnies, and I will wear them with dresses until the day I die. My winter work uniform is basically a dress, leggings, boots and a long cardigan or denim jacket. It’s like wearing pajamas to school, but it looks cute, is warm and is super appropriate outfit for a first grade teacher.

      • I’m with Megan, I never stopped boots and midi skirts (even though I had to buy vintage/thrift versions until they came back in). I highly recommend blondo waterproof boots—waterproof and totally normal looking—for those of us you need to dress for work but also walk thru multiple snowy/slushy parking lots daily.

  2. I still and will always love knee boots and dresses/skirts in cold weather. But right now, I’m still all about my OTK boots with jeans. It still looks really fresh and fun to me.

  3. Nice post! i usually stay away from denim over denim, but you make this look so cute, love the colors of the denim and boots together! the dress is really pretty. i noticed that prints are so in now. darn just when i am starting to go minimal basics, no prints. hard to keep up with the trends…

  4. I probably will opt for OTK with jeans and leggings but I LOVE them with the midi dresses/skirts. Thanks for doing this post though because I had a friend ask me my opinion on this last month and I was at a loss to try and remember when it was that the trend came out strong and I can’t believe it was 10 years ago already!!! ?

  5. I had been wondering about tall boots. Thanks for the ideas! Related(ish) question… wondering about wearing my wide-leg crop denim into the fall – maybe with tall boots underneath? Crazy?? Or do I just stick with a sock boot… or put the crops away til spring…? Ideas welcome!

    • Sooooo…. I follow a bunch of British moms (“mums,” heh!) on IG and they’ve been into the wide leg cropped denim for a while. Last winter they were wearing them with- I kid you not- black tights and white tennis shoes (Jack Purcell, adidas superstars) or black vans.

  6. These outfit ideas are appreciated! I love the look of OTK boots on others, but as a “hippy” pear shaped lady they’re just not flattering on my figure. I’ve been looking for ways to keep my knee high boots current. Thanks for the suggestions!

  7. Love all the different looks with the knee-high boots! I’ve neglected mine for a few years now, opting instead for ankle boots (which is my favorite style of boot). I finally bought OTK boots last year and I’m hoping to break them out again soon.

  8. Off-topic, but I love that lay-out where you have all the different options next to each other and with the prices really easy to see!!!!!

  9. Thank you for this post! I love posts that show updates for things likely already in our closets. We just moved and I contemplated donating my boots, glad I held on to a pair or two. I’ve been looking for a way to wear the wrap dress besides over jeans this fall and this is perfect. I just love all these looks and am salivating over those high waist button up jeans.

  10. Stop it! Just stop it! S you look so fabulous in all these outfits! The first is fantastic and they just kept getting better! Keep it coming…love your suggestions. The super high waist jeans are not for the short waisted lady with the big ummmm…..girls, nor is the cinched waists of the midi dresses, but I’m going to try to look for some alternatives since I completely dig the vibe.

  11. Shana, love these looks but gotta point out: in the era of ruffles and floral midis, has your trademark tomboy/glam style just gone a little bit more, dare I say, girly??

  12. Love be the looks! Personally, I don’t care if tall boot/jean combo is a bit dated – still love the way it looks and it’s practical (keeps my feet and legs warm and dry)!

  13. When I started teaching 16 years ago I wore knee high boots and jean or corduroy skirts all fall/winter. I think I over did it. I’m not ready to do it again, plus I’m 16 years older… I’ve kept my knee high boots, but did not pull them out of storage once last year, and probably won’t this year either, but I think your first look is pretty awesome. Currently loving cropped high-rise jeans (and now that I’m 16 years older I feel I can dress more casually at school, a plus of aging!). I think this winter I’ll wear cropped pants with socks and ankle boots, so I’m looking forward to a post about that.

  14. I especially love the first look. Question about that dress–does it have any stretch? I have a similar dress but I don’t wear it often because it just isn’t that comfortable (no stretch).

  15. I love your hate of the jeans look. It’s certainly practical, as TMM says! On me, monotone is more flattering. On you, the contrast is cute, even if you do look annoyed. 🙂 I’ve pulled out my tall boots and will work them into an outfit, one of those days I manage to shower.

  16. I’m digging the ankle boots more than the tall boots right now (just can’t/won’t do the otk, although I don’t mind it on someone else). But as it gets colder, the ankle boots are less appealing for practical reasons. If you don’t wear tall boots in the winter, what do you wear or how do you style your booties and sneaks in a way that still keeps you stylish but warm?

  17. In Tampa, Florida we wear tall boots with jeans and leggings the second the temps drop below 60; because in two days it’ll be right back up to the high 80’s! ??‍♀️

  18. Thank you for this post! This question about tall boots was exactly what led me to realizing I needed to seek out some style advice, and was referred to your blog. While aesthetically I love the tall boot/skinny pant look, I noticed I was starting to feel dated when I wore this combo out and was looking for someone to tell me if that was true or not. Thank you for being honest & straight to the point, that’s what I need. I love the look with the midi dress.

  19. As I’ve gotten a little older I’m a bit more curvy Vype high rise jeans just don’t look good on me. Any suggestions on how to update my denim look?

  20. I agree re knee high boots looting *dated* or meh over jeans. But otk boots are intimidating and give me Julia Roberts ala “Pretty Woman” flashbacks. Even when the heel is mid to low. Will you please do a post on styling these with shopping links?!

  21. Tall boots are still a popular choice for dresses & skirts for the office, where ankle boots can be too casual & OTK boots are too ?. Style with more work wear S!

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