September 19, 2014 - Easy Outfits, Style, The Next Thing You Need, Trend Watch

Five Ways to Wear Ankle Boots

how-to-wear-ankle-boots Want to know what the most burning question has been on GYPO readers’ lips lately?  I’ll bet you can guess from the title.

How the heck do you wear ankle boots?!?

They’re cute, no doubt, but these little buggers can be a bit tricky to style.  When I bought my first pair, they sat in the closet for almost an entire season with no wear.  When I finally got up the nerve to pair them with some jeans, I was hooked and eager to find other ways to wear them.  Before long, I was experimenting with all kinds of ways to pair them up and ready to add to my ankle boot collection.

Here are five of my favorite ways to pair up ankle boots.

1.  Ankle Boots with Ankle Jeans

Well, duh, that just makes sense, right?  Ankle jeans were practically made for ankle boots and retailers are getting on the bandwagon with this trend.  There’s hardly a store you’ll walk into this fall that doesn’t have some cute ankle jeans that are the perfect length to fall just above your ankle boots.

Embellished Sweatshirt Jeans Full 2

2.  Ankle Boots with Cuffed Skinny Jeans

If your skinny jeans are longer than ankle length, just cuff them right above the top of your boot.  Easy peasy!

gray-jeans-teal-shirt-full

3.  Ankle Boots with Boyfriend Jeans

Take a cue from Rosie Huntingdon-Whiteley and pair your slouchy boyfriend jeans with a cute pair of ankle boots.  Throw on a t-shirt, scarf and jacket and you’re instantly chic for fall.

Rosie Huntington-Whiteley. I'm going to have to try the boyfriend jeans with booties style.

Or try the trend with a military jacket and white tee.

Fall outfit ideas. Military jacket. White tee. Nude scarf. Cuff jeans. Cognac suede ankle boots. Rachel Bilson in the Harrow Boot

4.  Ankle Boots With Socks

Scrunch some wool socks above your ankle boots when pairing them with skinny jeans or leggings for a cute and cozy look.

jambu-perla-brown

5.  Ankle Boots With Dresses/Skirts

Swap out your typical heels and try a pair of tights with ankle boots this fall.  It’s a modern look that’s sure to instantly update your outfit.

10 Ways to Wear Ankle Boots | Monochromatic | A monochromatic look is a great way to wear those taller ankle boots...a pair of black tights and a black pencil skirt creates a sleek long black line that makes it so the height of the boot is irrelevant.  Tip #8. Try a fun patterned top to offset the monochromatic bottom! Tip #9. Try brown tights with brown boots, gray with gray, or mustard with your light brown boots! Shopping Options

[Ava Ankle Boot]

[Hartley Ankle Boot]

[Lace Up Bootie]

[Suede Ankle Strap Boot]

[Whysper Ankle Boot]

[Suede Low Heel Ankle Boot]

[Vince Camuto Ankle Boot]

It’s Your Turn:  What’s your favorite way to wear ankle boots?  Tell us in the comments.

Stay tuned for an announcement about the Fall Style Challenge on Monday.

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Getting my pretty on with The Pleated PoppyOne Stylish Mom and Erika and Andrea.
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51 Comments

  • great tips, I love ankle boots.

    xo
    ​PinkSole​

    • They are fab to wear!

  • Love this post!! I’ve picked up a few pairs of ankle boots. Love your options too! Might have to get another pair! Have a great weekend!

    • Thanks Katie. I’m thinking of getting another pair too! Have a great weekend!

  • I remember when ankle boots first came out I was all “Those are weird. Not a fan.” UM….now I have 3 pair. A pair of TOMS taupe suede wedge ones, a pair of Target black suede ones (that look like the TOMS), and my favorite BP pair I scored at the anniversary sale this year. LOVE MY BOOTIES!!!

    • I love your collection. 😉 I’m hooked! SO in love with my booties!

  • Mary

    Love booties! I had none until last fall and now I have 7 pairs with one more on the way….love the gray suede ones I just got from Gap! But my favorites are from Target! For girls with “muscular” calves that have a hard time with finding tall boots to fit, booties are great!

    • BEAUTIFUL! I love Target booties. I’ll have to check to see if they have the gray suede ones from Gap.

  • Love your posts and tips! Can you try to provide some flat heel/low heel options sometimes for those of us who can’t wear heels? I can’t wear anything over an inch. I’ve become the queen of oxfords lately, which thankfully are in style now!

    • Denise Z

      I’d love to see these options, too!

    • Hi Diane! I’m planning a post all about oxfords. 🙂 Hopefully that will give you some ideas. Most of the ankle boots and booties do have a bit of a heel. That’s why I prefer riding boots for my every day boot.

  • I love ankle booties! I agree, styling them can be tough. Such great options, photos and tips. Have a wonderful weekend!

    Audrey
    http://www.audreysalutes.com

    • Thanks Audrey. Have a gorgeous weekend!

  • Love your tips! For the longest time I didn’t buy booties because it just didn’t seem right me wearing it.
    Red Reticule

    • I hope today’s post gets you to experiment with booties! You will love them.

  • Jill

    It is really not my intention to hurt anyone’s feelings but … I just can’t help feeling that this style of shoes is going to be one of those things that we look back on later and think, “What on Earth were we thinking?” Do they flatter your legs?–no. Do they flatter your feet?–no.? Let’s face it, we women dress more for each other than for me, and I don’t think that is wrong. But, do yourself a favor, ask a man what he thinks and brace yourself for the honest answer.

    • I really think it’s all about how you pair them. With a skinny jean or slim pant, they can be a very flattering alternative to high heels. I do know my husband’s opinion on them, he just bought me a cute pair for my birthday. 🙂

  • Courtney Taylor

    Bought my first pair in spring 2013- an adorable cognac Steve Madden pair- after seeing then on one of my favorite bloggers on IG all winter long. I couldn’t wait to wear them when fall came! I bought two more pairs last fall and I’ve since added another pair- the Hartley Ankle Boot you featured (which are AMAZING by the way!) I seriously LOVE my booties!! I’m most excited to try them with scrunched wool socks this year!

    • LOVE the Hartley boot, those are on my wish list! Can’t wait to see you styling them with wool socks, it’s such a cute look!

  • I have a couple pair of ankle boots and they are perfect for our warm winters here. Great tips!

    BTW, I host a weekly link up on Thursdays and hope that you will join me.

    Alice
    http://www.happinessatmidlife.com

    • Which pair is your favorite Alice? Thank you. I’ll remember for next link up! 😉

  • I looooove ankle boots! Lots of great looks here. Where did you get that cream crochet looking top in that first photo? I LOVE it!

    I have another post idea/request for you. (Hopefully these aren’t annoying – haha! I just think of stuff I’d love tips on.) Some fall transition outfits for those of us that live in HOT places … you know, where it’s still not cool enough to wear a bunch of layers but still don’t want to be rocking the bright summer stuff.

    • Ashley, I got the lace cotton top at Loft. Unfortunately, they are sold out due to high demand. If I see any that look similar, I will let you know. Thanks for the post request. Great great idea! 🙂

  • I’m SO glad you did this post! I just bought a pair of wedge ankle boots and now I know how to wear them! Have a great weekend!

    • Perfect timing! Have a wonderful weekend Lana.

  • Great tips! I too had my ankle boots for 2 or 3 years before I even attempted to try them on…silly I know! But now I need more! In every color for fall, hehe.

    • You can never have too many ankle boots! 😉

  • I agree they can be tricky to wear & I have very skinny ankles so sometimes they look way too wide on me. These are all great tips!! Have a good weekend Alison.
    Marta, xo
    http://www.sweatersstripesandsweets.com

    • Have a good weekend as well Marta. Can’t wait to see pics of your ankle boots!

  • Carolyn

    Love them all! Inspired to buy a pair of red Frye ankle boots at TJ Maxx!!

    • That’s a beautiful color and a great find!!

  • Alison- I LOVE ankle boots!!! All your choices here and the way you have styled them are spot on!! My only question is the socks with the boots….hmmm…..I’m going to have to try that…you totally pulled it off! Also, thank you SO MUCH for linking up with me today. Thank you so so much!
    xoShannon
    http://www.onestylishmom.com

    • Thanks Shannon! You’ll have to give socks a try with your boots! You’ll look cute and cozy at the same time. 🙂

  • Daniela

    Can you wear ankle boots with leggings? I always see leggings with tall boots.

    • Hi Daniela! Yes and you can try them with the slouchy socks with leggings too. This works best with a long sweater or tunic over your leggings.

      • Daniela

        Thanks for responding! I bought my first pair of leggings this year. I am over 40 so I worry about looking inapproriate.

  • Love bootie season! Thanks for the lovely inspiration and tips!

    • I do too! So fun to pair ankle boots!:)

  • Becky

    Love the post so many great tips. I purchased my first pair of ankle boots and they are a wedge heal, would you pair them the same way you posted or something different?

    • Hi Becky! I would definitely style the wedge heel the same way. Cute!

  • Definitely some great tips! Living out here in San Diego where we were still playing in the pool during the day, ankle boots are PERFECT for the evenings. You don’t seem out of place, as I feel if I wear knee highs when the weather is still a little balmy. I need one more pair and then I can say I am GOOD this season!.

    Thrifting Diva
    http://www.thriftingdiva.com

    • I totally agree with you! What color ankle boots do you have right now? 🙂

  • I am a newbie here and I have enjoyed reading your older posts. As a gal who loves a good ankle boot, I really appreciated idea number 4. Just when I thought I knew every way O could wear my ankle booties! You can bet i’ll be sporting the look this fall. Thank you.

    • Welcome Brittany, so glad you are here to GYPO! There will be more great tips, keep an eye out for them!

  • Kathy Parker

    Hi! Loved this post! I appear to be collecting booties!

    One question for you: i can’t wait to try them with a skirt or dress, but was wondering about the tights. Should they always match the boots in color? Or would you pull out a complimentary color from the skirt? (Side note: I’m only 5’2″!)

    Thank you!!

    • Hi Kathy! You can wear any color of tights you want with the dress/skirt. They don’t have to match the boots. I’m doing a post soon where I pair them with a striped sweater dress, yellow tights and ankle boots. If you do all the same color, it does lengthen your legs.

  • lisa

    Hi! Just found your blog, love it! Love ankle boots too! Where are the ones you are wearing from? They are cute!!!!

    • Hi Lisa! Thanks so much! I hope you’ll stick around. Those boots that I’m wearing are all sold out but here’s a similar pair that I found: http://rstyle.me/~2zEsM

      • lisa

        Thanks for the response!!
        Well darn for being sold out!!
        I like that your wardrobe consists of items that are in a nice range of prices, not all high $$, and a lot are really reasonable. I actually found some really neat pants that I love from Old Navy at a great price!
        And, I took your lead and ordered a couple pairs of jeans from Loft, can’t wait ’til they get here!
        Thanks again for reviving my interest in clothes beyond my typical yoga pants or jeans and hoodies!!!

        • They sell out fast. So sorry. 🙁

          Thank you so much. You will LOVE your Loft jeans when they arrive. You won’t want to wear a different pair of jeans again!

  • ally

    Hi, I love your blog. was wondering what handbag is that on the picture with the soft pink pants ? I love it !
    thanks