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!


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.


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.

Fall FB Cover Graphic White Learn More

Getting my pretty on with The Pleated PoppyOne Stylish Mom and Erika and Andrea.
Get Your Pretty On diagonal divider

Get your free Closet Staples Casual Capsule Wardrobe shopping list + four free outfit ideas!

  • This field is for validation purposes and should be left unchanged.


  1. 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!

  2. 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!!!

  3. 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!

  4. 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!

    1. 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.

  5. 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.

    1. 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. 🙂

  6. 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!

  7. 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.

    1. 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! 🙂

  8. 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.

  9. 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!

    1. 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.

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

  10. 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?

  11. 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

  12. 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.

  13. 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!!

    1. 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.

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

      1. 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!!!

        1. 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!

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

Comments are closed.