Fresh Ways To Wear Tall Boots



All last week, Superman, Raines and I were relaxing oceanside in Gulf Shores.  We had gone down to visit my parents, who, since turning sixty-something have become devoted snowbirds.  

My parents didn’t want to move to Florida, but they turned sixty, and that’s the law. – Jerry Seinfeld

Also?  Weather channel. To say I returned home well informed about the snowstorms swirling about the country would be an understatement.

Anyway, fearing the worst, I had tall boots on the brain, expecting that we'd all be tromping around in snow up to our eyeballs.  Nope.  None, nada, nuttin'.  

But still.  I haven't worn tall boots all season, and I was (shockingly) in the mood.  So here are a few tall boot outfits for early Spring/Late Winter:

Leggings + Printed Shorts

I'm completely sick of tall boots over jeans, but leggings?  I'm still in.  Not sure what makes the difference, but the leggings + tall boots feels a bit mod.  I like mod. 

DSC_3394(wearing: coatsimilar here… sweater –  similar here thanks to Belinda for the find… shorts – last year's Target shorts or try this year's in neon or jacquard print, or these from Forever 21… bagMOOP waxed canvas Paperback Clutch in brownboots - vintage fryes) 

And there's nothing wrong with floral shorts, any time of year (especially when purchased at Target for peanuts).


Dress + Printed Tights

Printed tights make everything feel fresh.  And it's hard to argue against pink polka dots for Spring.


These boots, BTW, were M's.  They were a vintage Frye score on Ebay.  Sadly (hee hee), she went up a half-shoe size after one of her pregnancies.  And guess who happens to be a half-size smaller?  Yessssss.  THAT, Mamas, is a good friend. 

The other boots (from the first set of pics) are, oddly enough, almost the exact same boot.  Vintage Fryes, gifted to me by a co-worker eons ago.  Yup.  You read that correctly.  I have been gifted – TWICE – with amazing vintage Fryes.  Since I am typically unlucky (seriously – someone did my "numbers" once and pronounced me the "second unluckiest number"….only to be beat by my husband who is the unluckiest number) I. WILL. TAKE. IT.  And never, henceforth, go out in a storm. 

You can still find these boots on ebay, actually.  Ranging in price from $5 (seriously) to $299.


 (wearing: dress – BCBG, similar hereshirtAnthro washed denim button-down….tights – Kate Spade, similar here….boots – vintage Fryes from eBay)


Also loving….


Yes, this is tall-boots-over-jeans, but I love the updated proportions with a tucked-in top and swingy cape.  Perfection.


(photo credit: Mrs. Whiskers Closet via Chictopia)


Or tall boots with lightwash, destroyed denim and thin, cozy layers.  This is my next attempt. (Of course, my tall boots will have a lower heel.)

(photo credit: It's Not That Deep)


Lastly, how about tall boots, a twirly skirt and a drapey top?  Bonus if the skirt is faux-leather (I'd just throw leggings under the whole thing and call it good.)

(photo credit: Chictopia)


Any other new styling ideas for tall boots?  Or have you just…moved…on….??




  1. I’m so thankful for this post because even though I’ve really been trying to do the bootie thing this year (oh, how I’ve tried!!!), I always end up feeling too elf-ish or too dumpy. Perhaps just haven’t found the right pair. Anyway, I’m still stuck on my taupe-ish BCBG tall boots. Like ’em over black leggings with a long blouson style tunic that covers my rear (which reminds me how very questionable that kind of outfit is–using leggings as pants!). Appreciative of the affirmation that tall boots are still acceptable. Thanks again!

  2. Please don’t say tall boots are going to go away. I am just feeling really comfortable wearing them and without a little baby literally attached to my chest all the time I have been FREEZING this winter. I want to know that tall boots will be keeping me warm for years to come!

  3. Yeah, I’m with lauren. Booties work with the “same color tights thing” and also under a longer trouser for work, but booties and leggings or booties with a skinny DO NOT flatter my 5’4 curvaceous frame. I end up looking like an ice cream cone gone wrong.
    THOUGH: I was watching an episode of What Not To Wear the other day on Amazon…and I saw a petite gal in a nude-y suede bootie sans tights which actually elongated her legs because she was so pale skinned (like me). I was impressed.
    But yeah. Tall boots. Need them. Black suede stacked heel tall boots are a non negotiable in my wardrobe. I even got away with a pencil skirt and NO TIGHTS with a blowzy top and a blazer last week and looked fierce. I live in New England so this is remarkable pre-May…

  4. Oh thank goodness your back! I missed seeing the outfits! thank you:)This blog is like daily “crack” to me?!Well I don’t usually wear tall boots…I really like booties and wedge sneakers! Would love to find a vintage pair of frye though!Hmmm

  5. I’m wondering where you get the black leggings? I’m not sure where to buy some…
    I really like that dress and printed tights outfit the best!

  6. I have three pairs of tall Fryes in the same style!!! What’s wrong with me? (Jane Strappy, love love love in black, brown and fatigue gray). I wear them all the time, with jeggings and huge sweater, matchsticks and a school boy jacket, winter shift dresses (the stretchy thick kind, like the J Crew Jules only cheaper and washable) and leggings, all of my old work sweater dresses from when I used to go work get dressed down with these boots and a turtleneck.
    I can’t believe you’ve gone all winter!! I wouldn’t know what to wear if not for my tall Fryes!

  7. I will be very sad if tall boots go out of style. I may still wear them anyway. I have a pair of burgundy Fryes that I adore, and have worn all winter, as well as two-toned riding boots and over-the-knee grey/tan suede Seychelles boots. I usually pair boots with jeans or leggings, but I LOVE those polka dot tights – I may have to pick up a pair for myself!

  8. We’re going to Florida for spring break in 11 days (but who’s counting?) and warm balmy days cannot come soon enough. This past weekend’s weather here in DC was a lovely sneak peek.

  9. I read this and thought of you guys:
    “Women always try to tame themselves as they get older, but the ones who look best are often a bit wilder.”
    Miuccia Prada

  10. Oh how I love that sweater dress! Wish it was still available.
    I’m still on tall boots and jeans, or tall boots and pencil skirts for work. And I love my tall Fryes so much that I can’t see that changing anytime soon.

  11. I can’t imagine tall boot going out of style..I have just come to consider them a wardrobe staple. A class. Like a black cardigan, a button-up white shirt, or a trench! BUT, I love these fresh ways of wearing them! I just can’t get over the look paired with the sweater dress and patterned tights..LOVE! (And I also can’t get over getting gifted TWO pairs of Frye Boots…who has an unlucky number? Hmmmmm? 😉
    And yes, where did you get those leggings from? Do share! ha!

  12. I am loving the looks- especially the destroyed denim and light layers, as well as the leather skirt. Look forward to seeing your interpretations! As always- you rock! xo

  13. I think they’re staples too. They won’t go away; they’ll just be styled differently. I’ve had tall boots for at least a decade (and I’m not a trendsetter in any way), and I originally bought them to wear with skirts when I was a teacher. I never would have guessed that I’d end up wearing them over skinny jeans a decade later. It’ll be interesting to see how I’m wearing them in another 10 years.

  14. Aww, totally off topic, but when my first was a newborn, I used to spend hours walking around that shopping center with her! She would only reliably sleep in her stroller, and I got to shop, so it was a win-win, haha. And she still likes to shop.
    On topic, please don’t take my tall boots away! Love the look with the patterned tights!

  15. No way!! Small world. 🙂 And don’t worry about the tall boots – they aren’t going anywhere. They are cemented firmly as classics. I (personally) happen to be sick of them over skinnies. But they are still fabulous, and even the boots-over-skinnies will be back in no time. 😉

  16. Megan – WHOA, girl. That was *really* well said. Yes, yes, YES! Any bets on how we’ll be wearing them 10 years from now? Hmmmm….probably under bootcut denim (snort) or…WAIT! Remember those gaucho pants? LOL! That’s my prediction: 10 years from now under gauchos. 🙂

  17. There was a time when they were ALL I wore! Seriously. EVERY fall/winter/early spring day for almost three years. 🙂 I think we just needed a break, LOL. 🙂

  18. Sounds fab. And pre-May? Whoa. Nice.
    I still think petite+curvy and ankle boots can be done…I just need to find myself someone to experiment on….any locals wanna play? 🙂

  19. You know how I love leggings-as-pants. Right or wrong, I love it!! 🙂 Your outfit sounds amazing.
    But if you are feeling elfish in ankle boots…I suspect you haven’t found the right pair, or the right proportions. You should feel….hmm…mod? Rather than elfish. But I know what you mean – often, I put it all together and go NOPE. Then I do my elf-dance in the mirror, crack up the boys and change. Ankle boots can be fabulous, but they are SO MUCH HARDER than tall. Gah!!

  20. Depends on the price and how bad the stain.  (Such a wishy-washy answer I know).  Shoot me a link to our gmail and I'll take a look.  But I'm thinking they're probably fine.  God knows I treat mine like crap, and they hang in there really, really well.  Which is WHY I so love vintage Fryes.  🙂

  21. I’m blushing after reading your comment. And gaucho pants? God help us! (which is what I would have said about skinnies of course)

  22. Love these looks. When you first posted this, my silly Southern brain said, “It’s 70 and it’s Atlanta. No need for this business!” Lo and behold, it’s like low 40s this weekend. I’m trying the shorts/ tights/ boots combo today. Thanks for all your help, as usual! You rock.

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