How to Wear Ankle Boots with Jeans & Pants

This past week, I received a reader request from Lauren via the Sonia Styling Facebook page:

“I was just wondering if you could do a feature on how to wear ankle boots with pants? I have lots of skinny leg pants and feel like I need sneakers or flats with them. My last ankle boots were horribly slouchy and I need to find some that work for me but I am a bit stuck.”

I’m still mastering the art of the ankle boot myself, but I love a challenge – so I happily accepted Lauren’s request…and promptly went off to buy myself some ankle boots (purely in the name of research, if Mr Styling is reading this).

Hot tip: if you’re unsure about a certain item of clothing and want to give it a go, hit up one of the chainstores to buy it. In this case, I went to Kmart as I knew I wanted 2 pairs but didn’t want to spend too much. I managed to score the neutral pair for $25 and the black pair for $29. I chose these 2 colours, as neutral tones are the most versatile and a good place to start.


 Tips for wearing ankle boots with pants or jeans:

  • Always make sure you can see the whole ankle boot itself.
  • When wearing ankle boots with straight/slim leg or boyfriend jeans, cuff them so that you can see a hint of skin between the boot and the jean. You should only need to roll them up once or twice at the most.
  • If you’re wearing skinny jeans (or jeggings), make sure they tuck into your ankle boot with no bunching. Get your jeans altered if need be to achieve this streamlined look.
  • Ponte leggings are your Autumn/Winter best friend! Not only do they look like skinny black pants, they also hug your ankles making them perfect to tuck into ankle boots (like I’ve done with the black pair).
  • Choose a style of ankle boot that suits you. As you can see from the 2 pairs that I’ve chosen, they are different in colour and style, but both are structured and not slouchy.


How to style your ankle boots:

As you can see in the left picture, I’ve cuffed my jeans to show off the low cut cowgirl style ankle boots. I then added a white top, scarf and anorak to complete the outfit. This would be a great Weekend Uniform for anything scheduled into the social calendar from Saturday morning sport to a Sunday afternoon BBQ. It’s cute and casual but still stylish.

In the righthand photo, I’ve styled the black ankle boots with ponte pants, a longline striped top and a black trench coat. This outfit would be ideal for a fabulous lunch with friends or even a lovely dinner with your signficant other. I like that it feels dressed up, but is incredibly comfortable and practical. I have a feeling this outfit will get a lot of wear for me during Autumn/Winter!

If you’d like more boot inspiration, pop on over to Styling You to learn How to Wear Knee High Boots.

How do you style your ankle boots?

If you have a reader request, feel free to email me anytime ( or message me via the Sonia Styling Facebook page.

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  1. says

    Big fan of ankle boots. I actually quite like mine a bit scrunched around the top of the boot. I also love to wear them cuffed right above the top of the boot too.

    Excellent Kmart bargains too. I just bought a new style of ankle boot (for me!) which is a higher ankle boot, wider at the top but not slouchy. A Big W bargain. I’ll definitely be tucking into those!

  2. Josie says

    Love both styles Sonia you have done a great job styling them. Can i ask where you got the long top from in the second picture. I really love that look.

    • Sonia says

      Thanks so much, Josie. The striped top is from Sussan and it is so comfy it should be considered sleepwear!

      • Josie says

        Thanks Sonia. I really need to get to Sussans more!!! I bought the leather tights/pants on your recommendation and i absolutely LOVE them. Getting lots of great times from you. Thanks :)

  3. Donna says

    Love both looks – where did you get your ponte pants from? I’ve been a fan of the ankle boots with jeans for a few seasons but yet to try the ponte!!!

  4. tam says

    Am so happy I found your site!! I struggle with fashion, but you put things together Sonia that make a fashion fail like me feel like I can pull it off! So today while having my coffee with baby boy at the shops I saw this post about ankle boots and decided to take the plunge and bought a pair…very unlike me. Used your styling tips (had my skinny grey jeans on so felt “on trend”) and I think I pulled it off (Portmans had 25% off their boots today so $50, so took your advice of a cheap entry to the look). So thank you – you’ve given me the confidence to try a few new looks without thinking I have to break the bank.

    • Sonia says

      Oh Tam – what a wonderful compliment to give me! Thank you so much. Well done you for diving right in and giving it a go. Sounds like you’ve found a winning pair of ankle boots. I do love a good bargain! Have a fantastic long weekend.

  5. says

    Two great looks Sonia – you look gorgeous!

    I am a huge fan of the ankle boot and have a few pairs now (red, grey, brown and black), some are heeled, some are flat and I wear them all winter long.

    I generally wear my ankle boots with skinny jeans (just tucked in) but find they work best (on me) with tights and dresses. x

  6. Lisa mckenzie says

    Love how you have styled both of these boots Sonia I love all my boots and would like a new pair of cute ankle boots for winter!

  7. says

    Thank you so much! I went out today after reading your blog post and bought a pair of brown and a pair of black ankle boots. I told my husband they are my early Mother’s Day gift to myself! My Kmart didn’t have a great choice but luckily it was cardholders day at my local Farmers Department Store so I got a fantastic price on them with 30% off. I will have to take some photos to show you how I have taken your advice :)

    • Sonia says

      Yay, yay, yay! That makes me so happy to hear Lauren. Great work on scoring a bargain too. Can’t wait to see how you style them up.

  8. says

    I love this look, Sonia! Especially the black ponte pants. How good is Kmart for a bargain?!
    My best bargain ankle boots were a gorgeous bright blue suede pair from Wittner, on sale for $39. I wear them with skinnies or a floral dress and navy tights. I love coloured boots as they brighten up dreary winter days. :)

  9. says

    Oooh, I like this tip. Thanks. I don’t suppose you could give some tips on cowboy boots with skirts/pants etc??
    I was given some lovely Ariat boots…but don’t know what to wear them with. Seems a shame to hide them under boots!

    • Sonia says

      Cowboy boots… I think they look best with a dress (with or without tights) or with jeans/leggings tucked in. And just like ankle boots, you want to see the whole boot. Hope that helps!

  10. Wendy ashley says

    I have a question that I struggle with every winter- what works best UNDER ankle boots- particularly if you plan on flashing a bit of ankle/leg at the top of the boot? I think in this case flesh hose just aren’t gonna cut it!!! Knee hi’s are still going to show and I hate the idea of fishing around in the bottom of a boot chasing the sockettes I sometimes wear in ballet flats. Dilemma!!!!!

    • Sonia says

      Wendy, I totally get what you mean! I have a drawer full of ankle sports socks (that I buy from Big W or Kmart) that I tend to wear under ankle boots. I like the extra bit of thickness to make my boots nice and comfy. Plus my other trick is to wear said ankle socks under black opaque tights for extra warmth and comfort when wearing boots! Hope this helps.

  11. Jessi says

    I have a question… I love my new pair of boots and want to show them off. However, I HATE tight jeans/pants (jeggings, leggings). I do not like anything tight on my already too big thighs! HELP?! how can I wear my boots without these tighter type of pants?

  12. Anna says

    Hi Sonia,
    Loved this post. Great to see your ideas.
    I wanted to ask a question. I have a black skirt and a navy blue skirt and brown ankle boots. What colour opaque tights would you wear with each skirt? Also could you tell me the type i.e 70 denier etc.

    Thanks for your help.

    • Sonia says

      I truly believe you can never go wrong with a great pair of black opaque tights – no matter what you’re wearing. Black and navy is an especially chic colour combination. As for tights, I always go for at least 100 denier or above.


  1. […] The hat worked perfectly with the Lace Trim Shirt from Sussan that I’d recently bought – another purchase that wasn’t so obviously my style but I loved – and from there I added my favourite leggings from Sussan (faux leather at the front, ponte at the back) and a pair of black faux suede ankle boots from Kmart that I originally bought to write this post. […]

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