How to wear ankle boots

I still hear too many women telling me that they would love to have ankle boots, but they don’t know how to wear them, so they just don’t. I’m here to help! Keep reading for some visuals and tips on how to wear them. You can also see the video I did last year, for extra visuals 😉 And I’ve done another video on where the best place is to find them which you’ll see in my Instagram feed soon. 

Firstly, decide if your first foray into this style of boot is going to be a heel or a flat, or somewhere in-between. I think the in-between heel is a good place to start as a small heel is always more flattering than no heel, and also more wear-able than a killer heel.

In terms of how to wear your ankle boots, the most important thing is that you need to show the boot.

For skinny jeans – your jeans either need to sit inside the ankle boot, or bunched just on top of it like this:

Or you can cuff them like this: 

Leggings or tights will naturally also need to sit inside the boot.

If you’re rocking the wide leg jeans that are everywhere right now, then they need to be cropped and they can sit just onto, above or even just below the hem of the jeans. I forgot to take a photo of me in wide leg pants with boots so google it on pinterest for visual inspo, sorry!

NOTE: You absolutely CANNOT wear ankle boots with bootleg jeans, you’ll look like my mum.

If you’re buying your first pair I’d suggest going for a neutral colour i.e. brown/tan/black.

A lot of my clients have ‘big’ calves, actually they aren’t that big but for some reason most shops cater for run-way-model-type figures and if you don’t fit within those parameters it makes shopping tricky.

So stop trying to squeeze into knee-length boots that just aren’t comfy and also make you feel like your calves are gargantuan. Just go for ankle boots. They will elongate your leg and are generally more flattering than knee length boots. They also have way more of a ‘cool’ factor than knee length boots and are so much more versatile, so go on and get yourself a pair;-)







This Article Has 4 Comments
  1. Toni says:

    What about bootleg jeans?

    • Pippa says:

      Hi Toni, personally I’m really not a fan of bootleg jeans as they look dated and are difficult with shoes, but if you want to wear them then they’ll look better with a pair of pointy flats, not ankle boots 🙂

  2. Estelle says:

    Hi. I want to buy myself n pair of Pesso navy ankle boots but I also need a pair of shoes to wear with my thick winter stockings with my winter dresses. Can I wear the boots with my dresses?

    Thank you

    • Pippa says:

      Yes absolutely! But it can depend on the style i.e. not all ankle boots work so well with dresses, you’re welcome to send me a photo and I can advise you?

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