Bootie DOs and DONTs from A Chic Critique

When Blair asked me to do a post on ankle booties - how to wear them, and what to wear them with - the stylist and fashionista in me said YES! A lust-worthy look for fall, ankle boots are yet again making an appearance this season. While I tell friends and clients repeatedly, "not every trend is for everybody," (so no pressure), I'll leave you with a few different ways to incorporate these boots into an outfit (as well as a few tips to keep in mind).

Seeing as most of us aren't blessed with Gisele-length legs, here are some tips to fake it:

  • Look for a low-rise bootie, as a higher rise will truncate your legs. The goal is to elongate your gams - so look for a cut that scoops below or across your ankle bone.
  • Stick with a monochromatic look. Short booties can easily cut off your legs, but wearing the same color tights & booties is a great way to create the illusion of long legs and lengthen your silhouette.
  • A looser-fitting bootie will prevent your legs from looking chunky - so look for a boot that doesn't squeeze your ankle too tightly.

So, what do you wear ankle booties with?

  • DO wear them with skinny jeans, with the hem meeting the top of the bootie - the purpose is being able to see the boots, not cover them up!
  • DO wear them with a flowy skirt or dress (preferably one that is not uber-fitted). The length of the skirt/dress will depend on your height: higher hemlines elongate shorter figures.
  • DO wear them with slim-fit leggings or opaque tights - again, stick with a monochromatic color palette (think black with black, grays with grays).
    Ankle Booties
{click photo to check these items out on polyvore}

what not to wear:

  • DON'T wear them with long, flowy dresses.
  • DON'T wear them with longer skirts (hello, no-no).
Love 'em, like 'em, hate 'em - what do you think? Will you be rocking some ankle booties this fall?

stay chic,

Annie from A Chic Critique, Nashville, TN

P.S. Blair - thank you so much for inviting me to guest post today! So much fun! I think you and your blog are pretty wild & precious, too.


  1. ooo fun tips and picks!! Thanks ladies!

    Hope you have a fabulous long weekend!

  2. Yay baby! I'll be rocking them indeed and i so love the looks you created! xx

  3. I *love* ankle boots - so glad they aren't "over" yet! Thanks for the great styling tips!

  4. Love the looks you created and that elizabeth and james blouse is to die for!

  5. GREAT to know!! I am really not sure if I can pull them off, but I bought some (online) so we shall see ;)

  6. I'd love to, unfortunately the cankles that my mother gifted me with will not allow me to accentuate that part of my body... boo!

    fab tips though!
    xo tash

  7. I am in luv with ankle booties! I wear them with jeans, skinny pants and mini's!

    Thanks so much for contributing to the Fall Wardrobe Challenge and filling my closet with goodies!! Keep your fingers crossed Polyvore picks us!

    Have a fantastic weekend :)

  8. I bought a pair a year or two ago, thinking that I'd wear the heck out of 'em... And I'm sad to say that I reach for them the least. I think they're SO cute on everyone else, but I'm not so sold on the short bootie on my figure... Maybe it's just the ones I bought? Hm...

  9. Great and oh so right do's and don'ts and I love your choices!

    Liesl :)

  10. YES ankle boots are awesome and i agree with your assessment about what to wear them with (or NOT to wear them with)

  11. love those grey ones. i found a cheap pair last year with bows on the back that i plan on donning again this fall. great tips!

  12. I noticed the non-tight fit, slouching to reveal the ankle thing about booties myself. I have a few pairs, and am contemplating a few wedgie bootie now.
    I like wearing them with body-conscious long-sleeved mini dresses (and dark tights in winter).

  13. these are some great pointers and i shall definitely keep them in mind now on... i like teaming mine with leggings and tunics the best!


  14. I have some black ankle booties myself, so I appreciate all of the tips!!!

  15. I agree. I've been seeing women around wearing booties who could DEFINITELY use some advice like this. I wonder if there is a limit to the type of body booties look good on - I'd love some booties but I'm worried my big hips, and big boobs combined with booties would make me look strange. Or am I just being silly?

  16. Great tips. I love these boots and look forward to incorporating them into my look this fall.

  17. Oh yes - lovin the booties already and seeing another pair in my near future.

    Thanks for joining Baby Space! I'm happy to be your newest follower :)

  18. Fab guest post, dear! I'm obsessed with black suede heeled booties right now -- the taller the better. SO pretty!
    xo Josie

  19. ooo this made me excited to wear them!!!!

  20. Those are such a great tips:)...I so want to wear them now:)

  21. I loved this post! I have booties similar to the grey ones.... pretty much the same. And this gave me some great inspiration on what to wear with them. I have only worn them a couple times because I haven't been able to wear them right.


  22. Ohh I loveee ankle booties. So glad I am purusing your old posts. I am WAY WAY behind Miss Blair :(


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