How to wear ankle boots with jeans

Wardrobe boot camp: how to wear ankle boots

Nikki ParkinsonFashion, How to 84 Comments

Editor’s note: This is regular series in which we help Styling You readers solve a particular wardrobe or clothing crisis with a little advice and some shopping suggestions. If you think you’d like to be considered as part of a Wardrobe Boot Camp post, then please email me ([email protected]) with a couple of photos and a brief run down of what specific help you would like. 

Mandy is a mum of three. She also blogs at A Little Space Like Home. She says her blog helps her to create a beautiful life in the everyday.  “I want to create memories for my children, so on reflection, they will look at their life with love and walk into adulthood with joy and passion”. Mandy wrote to me asking for some help with how to work ankle boots into her autumn-winter wardrobe. And I’m so glad she did. It’s a first world issue that needs attention. Have you seen how many ankle boots are out there? They cannot be ignored. Well, they can, but why would you want to?

Mandy | A little space like home

The Plea

Why do I feel like such a tool with skinny jeans ankle boot combo?  Clearly it’s all the rage at the moment and I love the look on everyone else. I’m not sure if I’m just being too hard on myself, feel uncomfortable, or am just not pulling it off right. 

I wore them as above but also with skinny jeans on the weekend but it was all scrunchy and just didn’t feel right. Then my hubby walks in the room and goes, “whats with the bottom of your jeans?”…  you know, to make a person feel even worse.

The Tips

1. The main thing to remember is for the ankle boot thing to work, we need to SEE the ankle boot. You don’t want fabric flapping around them. You want your leg to look streamlined.

2.  To achieve such a degree of streamlined-ness (so not a word but you get my drift, don’t you?), you have three options: wear with either skinny jeans, legging/tights or bare legs. That way the boot kind of becomes an extension of your leg … does that make sense? If said jeans or tights are too long for you, get them altered. If this frustrates you, spare a thought for our long-legged, tall friends who simply cannot find jeans long enough. They can’t get them altered in reverse, can they?

3.  Because I’m fickle, I’ll add in another option, wear with slim or boyfriend jeans that have been cuffed. Cuffed so that you see the boot. So same theme, just a different, more-fashiony look and therefore more difficult to perhaps pull off.

4.  Re boot colour, I say if you’re building your boot wardrobe from scratch stick with a black or nude/tan neutral option for starters. Already got those nailed? Add in a colour because why not?

5.  Re boot cost, I say buy the best your budget can afford. Boots in a classic style will never date. Some actually get better with time. And if you live anywhere like I do, they only come out for a few months so can be looked after and worn for many years. Cost per wear, Stylers. Cost per wear.

The Shopping

Let’s start with the boots … all featured are available at Style Tread. Click here for even more suggestions.

Ankle boots autumn-winter 2013

1. Zoe Kratzmann boots $330 |  2. D.Co Copenhagen boots $375 | 3. Boston Belle boots $179.95 | 4. Zoe Kratzmann boots $299 | 5. Mollini boots $189.95 | 6. Mollini boots $189.95 | 7. I Love Billy boots $79.95 | 8. Windsor Smith boots $149.95 | 9. Florsheim boots $199.95

And a couple of outfit options …

How to wear ankle boots with a dress

1. Leona Edmiston Ruby dress $179 |  2. Witchery trench $249.95 | 3. Metalicus leggings $39.95 | 4. Sussan scarf $59.95 | 5. Mollini boots $189.95


How to wear ankle boots with jeans

1. Bardot jeans at Birdsnest $139.95 | 2. Country Road knit $129 | 3. Samantha Wills ring $69 | 4. Witchery scarf $69.95 | 5. Zoe Kratzmann boots $299

Have you got ankle boots already on high rotation in your wardrobe? Looking to buy a pair? Any tips for Mandy?


Comments 84

  1. Thanks , I’ve just been searching for info about this topic for a while and
    yours is the greatest I have found out so far.

    However, what about the bottom line? Are you sure about the

  2. I just discovered you 2 weeks ago & have already started changing my perspective on fashion & my wardrobe. Bought these Mollini ankle boots a year ago in Jan 2013. I have ‘cankles’ so can only wear jeans/pants for coverage. What colour jean/pant would look good?

  3. I just got these booties, I’ve been thinking if they’d look good with a mini skirt and a printed shirt with a jacket. Or if I should just wear them with skinny jeans/leggings. Also I would like to know your opinion when it comes to throw stockings over leggings or just while wearing booties with short skirts. Any help will be appreciated

    1. You’re supposed to tuck your jeans into the boots, otherwise people wouldn’t notice how awesome your booties are! (: (and if you pull your jeans over them it’d make your ankles look “fat”/funny shaped and it’d not make sense to wear boots if people’s gonna see them as if you’re wearing shoes) just show off those babies, that’s the fun part of wearing boots

  4. I always find that if I am trying a new style of shoe, nude colours are a great place to start! Nude, suede ankle boots with a low block heel (and no socks!) look great with cuffed boyfriend jeans or cuffed skinnies. The nude colour and matte texture of suede makes them disappear visually (if that makes sense?) which helps in becoming more confident with the style until you get used to the idea of them. Then you can be more confident with darker or brighter versions.

  5. Nikki, I have a fabo pair of dark purple skinnies and am at a bit of a loss when it comes to what to wear them. I have ballet flats- elastic patent black Walnuts with the bow, best ballets ever!) but not sure what to do with them for boots. I am thinking a fairly low cut bootie and the husband is saying brown. I found these cheapies at Rubi, what do you think?

    I tried to copy the image but it wouldn’t let me sorry

  6. Hi there, I love ankle boots and have them in black, I also have skinny jeans, leggings and long skirts to wear with them. First world problems is that I have just purchased the most beautiful pair of heeled nude/beige ankle boots and an wary of the whole cutting your legs off look. I know they are a great colour and go with everything but am not sure whether they just make me look clunky. I wish I could post a photo as they are so pretty! I’m 5’6 so am not overly vertically challenged, and a size 10. Any thoughts would be appreciated as I really want to keep them! Thanks

    1. Hi Lisle, you’re the same height as me and I’m wearing heeled nude ankle boots with denim jeans and a tunic … and you can post a photo here in the comment section. There’s a photo/scenery icon in each comment box.

        1. Definitely can wear those with skinny jeans! I’m thinking black, light washed, or even maroon. Beige/nude is a great colour for mixing and matching 🙂

  7. I bought my first pair of ankle boots today, to wear with skinny jeans. I’m a little apprehensive, but hope that I get it right. Your post really helped!

  8. Great post – so in love with all the ankle boots around, but slightly scared to try them out!

  9. I’ve been thinking about ankle boots for a couple of weeks. Inspired by this post, I bought a black pair today at at Joanne Mercer. Not quite tights weather yet but looking forward to wearing them with dresses/skirts. Thanks 😉

  10. Ah, a good refresher for winter. I am going to need some new jeans that FIT soon… I love this look. I may need to ensure I buy jeans that can be worn with an ankle boot. That means I will then ‘need’ ankle boots seeings as I have the jeans to work with them… (I love a bit of shopping forethought!)

    Great post!

  11. Thanks Nikki…I really needed this. The beige boots I bought just weren’t working and it is how I’ve been wearing them!! I had been trying the “fashion forward cuffed and it just wasn’t working for me…too far outside of my style comfort zone. Will try with my skinny’s and I need a black pair to wear with tights and skirts in winter.

  12. Thankyou for this timely post Nikki. I have bought some blue suede boots but haven’t worn them yet! I shall have to finally hem my jeggings (have just been wearing them cuffed under long boots) and hopefully the blue-on-blue will lengthen my short legs 😉

  13. I shopped for ankle boots last week. I came home with the Mollini boots you have pictured (no.5), the heel is a great height if you want a bit of a heel but not too much. I also got a great pair from Nine West called “Bogie”, so comfy!! I’ve been wearing them with my tube skirts and leggings, I’m shopping for skinny jeans tomorrow- may the gods of good jeans be with me!!:)

    1. Oh, so great to hear re the Mollini boots – and good on you for backing up with a pair from Nine West as well. Love the tube skirt and leggings look. Good luck with the jeans shopping. Remember it’s what you wear with them!

  14. Thanks Nikki I’ve been considering joining the modern age and buying my first ankle boots so this has been very helpful! Can I ask if the metalicus leggings you have shown are true leggings (i.e can be worn as pants with a longer top) or are they more like tights (i.e see through in parts)?

  15. I loooove ankle boots, I have a black pair and a grey pair on high rotation, but I also have a neutral suede pair that I have been a bit lost with – just couldn’t figure them out. I thought I would wear them with dresses in spring – but my legs are too too pale. I notice you have styled them with dark jeans and a jumper with a neutral touch – so I will try that out.

  16. On a recent whirlwind trip to Brisbane, I had to pack light and adaptable – out came my jeggings and a couple of long sweatshirt/cardigan combos, along with a great pair of Novo flat ankle boots. Not only was I comfortable, I felt as though I had made some small effort at looking put together without having to pack 800 items. This was a big step for me, because this time last year there is no way I would have been caught dead in that combo – I felt that it made my legs look smaller and chunkier and drew people’s attention to all the bits I wanted to hide. The ankle boots and pants combo is easy to put together and, now that I understand accessorising, easy to change up from day to night! Although, now I am thinking maybe I should have a black pair to go with my brown ‘cowboy’ style ones!!

  17. Wow, I’m not alone in this dilemma! I bought a neutral pair last year, they took me months to work out how to wear, then I loved them. About a month ago, I bought another pair – bright green snake skin – what was I thinking!!! They are beautiful but I have no idea how to wear them. Love your blog Nikki

  18. loved this post, thanks for the question, and the answers! i have ankle boots on the list, but haven’t yet purchased because of lack of knowing what they will work with in my wardrobe! i think i am more the dress and ankle boot person too.

  19. I am so pleased there are other people out pondering these very same issues – thanks Mandy for asking this question!! Love the post Nikki and your suggestions. I think I will just buy the entire dress option now. Devine!! It is just so me!

  20. Hi Nikki, gorgeous options there! I love ankle boots, and have around 4 pairs bought over the years. I have a caramel suede pair from Country Road, a cute pair of sparkly black ones from Seed and they look as though they will be on trend for this year also.
    Wittner are having a sale with many of their ankle boots $99.00! There are some great looking ones there. Not sure if you need to be a member or not though.
    Thank you for your posts, I enjoy checking in most days!!

  21. I bought some new ankle boots in Paris in December and they were everywhere! I’m so excited I can wear them again soon as the temps start to decrease. Thanks for sharing your styling ideas-I love them all!

    Best wishes,

  22. To those ladies lusting after that Witchery trench ……they are having a spend and save until 5 May….. 25% off when you spend $150… 30% off when you spend $250 (sign up as a Member its worthwhile) ….. suddenly that trench is looking affordable…. Happy Mother’s Day to you all lovelies!

  23. I embrace the tunic/leggings/ankle boots ensemble as well as the skinny jeans/ankle boots/knit ensemble.
    I have just started embracing the peg leg pants/fitted top/ankle boots ensemble too. Not sure about the Peg leg pants, will be posting the outfit on my blog anyways.

    Ankle boots are the new knee-high boots, IMHO.
    cilla xx

  24. Love the ankle boots. Could you suggest a good style or brand for comfort, when traveling on and off planes and a bit of walking. I have the jeans and leggings now all I need is a good pair of ankle boots. Thanks.

  25. I love me a good ankle boot! In fact I just bought some and they are yummy. Now I have the ankle boot, the skinny jeans & leggings – I just need to get the top half sorted!

  26. Thanks heaps Nikki. I’m going to be bold this weekend and team them with stockings and a dress, very bold for me indeed, but taking a leap of faith if you will.
    I also found that Sussan’s have an awesome range of Jeggings this season and they do sit so much better in the boot than my jeans did. My jeans might have been skinny jeans but they weren’t skinny enough down the bottom. Loving my jeggings/boot combo. Thanks again. Mandy.

    1. Oh brilliant Mandy – and yes, that’s the key, the jeans have to be fitting against your ankle – and at the right length for it to work which is why you’ve had more success with jeggings.

  27. Great Post Nikki,No I haven’t worn any yet,too hot as yet but I do own several pairs,black,tan and a taupe colour and I love them ,I always wear mine with skinny jeans and also with leggings or dresses,it’s a bit cool here today so I might do some trying on of winter garments 🙂 I also love a good knee high boot and you are so right about the quality my knee high boots have got better with age!I

  28. Love ankle boots! Well, love boots, but have a large number of the ankle variety in the collection. Down here in chilly Canberra, they get a work out most of the year – okay, not the hot days of summer, but the rest of the year, definitely!

    They work with skinnies, tights and leggings inside, bootcuts outside. Leggings or tights and a tunic, skirt or dress (short length is better with ankle boots, otherwise the legs can look very stumpy). Leopard print booties from last year – fun and versatile. This year’s purchase was motorcycle style (flat heel). So comfy!
    Tip – if the ankle boot is perfect but the fit is a little tight, consider having them stretched at a shoe repair place. I’ve got difficult feet and pretty much always have to get that done and it makes an enormous difference in terms of comfort.

  29. What about skinny jeans inside the ankle boot or is that old fashioned ,you would see the whole boot then,just remember there are no bad questions …..just people who don’t know what to wear???

    1. Never bad questions! The skinny jean inside is exactly what should happen with the above look but the jean needs to be firm around the ankle, not bunched in to make the ankle look cankle-y. Does that make sense?

  30. Spot on on the advise Nikki, I am short so I went for a light nude/tan colour to lengthen my legs and they’re great. My short pins look great in them, especially when I go shorter in dress length. I was actually overwhelmed by the choice, and decided maybe I needed several pairs and so I ended up at Target and found some great ones at $50 each, bargain! So when I find the right boot I will invest but for now, it’s fun to experiment and like you say we only get to wear these for a few months of the year over here.

  31. Nice work Nikki! I prefer ankle boots with a slightly higher and thinner heel, I think that’s how they are most flattering on me. Love, love, love that witchery trench, I think it needs to be mine!

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