How to wear ankle boots – an update

Nikki ParkinsonFashion, How to 51 Comments

There are many reasons why ankle boots are still very much a part of the winter fashion landscape.

For me, I think the main reason is that, unlike their knee-high sisters, ankle boots don’t discriminate on calf width.

Those of us with greater OR less-than-average thigh widths do not fear shopping for the ankle boot.

There is none of the potential too tight or loose around the calves/saggy around the ankle scenario going on.

They are ankle boots. They (generally) fit and they complete just about any winter outfit.

About those outfits … there is an uncomplicated science of sorts to ensuring that your ankle boots are working as part of your outfit.

It’s been two years since I wrote these how to wear ankle boots styling tips for a SY reader but they still hold true.

Tips on how to wear ankle boots

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.

Styling suggestions

Don’t just take my word for it. Check out this selection of ankle boot styling ideas from the real women of #everydaystyle. Make sure you search and check this hashtag feed on Instagram for daily style inspiration.

Dreamers and Drifters knit | Harlow jeans | Frankie4 Footwear boots | Johnny Was scarf

















Blue Illusion jacket | David Lawrence tee | Blue Illusion jeans | Frankie4 Footwear boots | Seed scarf


This winter it’s been all about the Frankie4 Footwear boot in my wardrobe – and I know many of you have embraced these -meets-function styles as well. Many of those boots are now sold out but you can find a selection here – or head to the stockist page for a store near you that may still have what you’re looking for.

Here are six more styles that have caught my eye online.

ankle boots winter 2015

1. Mollini boots $199.95 | 2. I Love Billy boots $139.95 | 3. Django & Juliette boots $189.95 | 4. Rollie boots $169.95 | 5. I Love Billy boots $99.95 | 6. RMK boots $189.95

So tell me, are ankle boots very much a part of your winter wardrobe? What are your favourites? What do you mostly wear your boots with? Got any ankle boots styling questions I can help with?

how to wear ankle boots #everydaystyle

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Comments 51

    1. Post
  1. Hi
    Just bought a great pair of DKNY wedge ankle boots. I’m not exactly skinny but there’s quite a loose gap between the boot and my ankle. Are they supposed to look like that? Not sure if I should return them because of this. Thanks.

  2. I have one pair that fit the simple ankle boot description – and they’re leopard print! My other two pairs are kind of hybrid, because they’re lace-ups. One a mustard yellow suede by Django and Juliette (LOVE their shoes) and the other a taupe suede pair that are a little less chunky by Steve Madden. Because my feet swell with RA, the adjustability of lace-ups makes a huge difference to how much I can wear them. Slightly different look, but it works for me 🙂

  3. I bought a pair of the I ♡ billy black ankle boots from style tread last week and they arrived on Monday – i obviously wore them teamed with black ponte pants to work on Tuesday! Can’t wait to give them a whirl with the skinny jeans for casual Friday at work as well. I love an ankle boot with tights for work dresses too, but given I work in a pretty corporate office, I need it to be a heeled boot rather than a flat. Really need to get back into taking an #everydaystyle photo again – I am definitely inspired by what I see online each day, both in how I use my existing wardrobe and what I am looking at to add to it.

  4. I have ankle boots on high rotation at the moment – a black suede pair for work; a leather flat heeled version for weekend sport sideline duty and then a camel coloured suede heeled boot for casual weekday outfits. Loving them!

  5. Nikki, I am so thrilled to be a part of this post. Thank you so much for including little old me. Not only are you fashion forward but you lead the way in making this blogging community so warm and welcoming. I’m so grateful – on both counts. xx

  6. I like a really nice looking pair of ankle boots. The styles that caught your eye are very stylish and the colours are just perfect to wear with lot’s of outfits in the wardrobe.

  7. I am only a recent convert and I love love love love my ankle boots!
    I have heeled ones in black, light tan and brown, and wear them mostly with black leggings or skinny jeans. I am quite tall but still like the heeled boots even though they make me look even taller!

  8. I am a new embracer of the ankle boot, love them. Do the Frankie 4 range run true to size? I have midget feet (size 5) and it can be hard to get 5s in some brands so I will often wear a 6. But if they run big I can’t do it.

  9. I love ankle boots ,I wear them nearly everyday in winter and another reason is because they are much easier to get on and off.
    Great post Nikki and gorgeous women in the style pics Xx

  10. I wear ankle boots to work almost every day in winter, by rotating through black patent, black suede, lace up leather.
    I used to be all about black opaques/leggings or skinny pants with my boots, but since adding in charcoal and grey, I’m hardly wear the black and feeling confident enough to cuff with not-so skinny jeans and pants.
    For me the key is not to wear completely flat ankle boots. They just seem to emphasize my hips whereas even a small heel gives me a little lift.

  11. I bought the Frankie4Liz boots after seeing them featured here on your blog and I can’t recommend them highly enough. I know I say this often to my husband about clothes that I buy, but they are honestly a great ‘ínvestment’. So ridiculously comfortable. However, be warned, they ruin you when it comes to wearing other shoes … I put a pair of very expensive black heels on yesterday and felt crippled by them. Thanks for bringing them to my attention.

  12. Just what I needed! Thanks for the tips from both yourself and my fellow readers! You all look fab.

    SSG xxx

  13. yes nikki! … love anything to do with boots and shoes!
    you look great and love the girls in their outfits!
    I love ankle boots especially flat ones! I live in them, if it’s not too cold!
    sometimes I get annoyed that my jeans or pants don’t exactly sit where I want them to so I roll them! … so I’m not bovvered! … throw on a scarf and jacket and all good! … enjoy your day hun! love m:)X

  14. I agree- great timing. I wasn’t sure about showing bare legs, as I have been wearing ankle boots with a pencil skirt for work, and just wasn’t sure.

  15. Oh good timing 🙂 What’s the basic idea about matching boot colour and tights/leggings again?
    I feel good wearing purple boots & black leggings but if the boots are closer in colour to my pair of leggings the lack of contrast feels messy sometimes. And I’m already messy enough! 🙂
    I had a look through your blog the other day but I think you may have tweeted about it a year or so ago so I couldn’t find it.

  16. I’m just getting to the ankle boot party and loving it. So far I’ve only been brave enough to them with leggings but feeling very inspired by your post and all those everyday stylers. So far I’ve only been brave enough to wear black, think I need some tan in my wardrobe stat!

  17. Thank you for featuring me Nikki! I loooove ankle boots and wear mine to death – most by the end of winter have seen better days! I find I wear them mostly with skinny jeans and dresses, and i used to wear a heeled pair to work. Great tips too x

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