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

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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.

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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.

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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.)

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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.

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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?

xo,

S