In Fashion and Beauty

This post contains affiliate links.

Wearing ankle boots with a dress wasn’t a trend I thought I could pull off, until my daughter showed me some photos of ankle boots on Pinterest and said, “This is how you do it, Mum.”

What to wear with ankle boots - the little black dress

So for this post I decided to take one pair of ankle boots, one little black dress, and style the look in four different ways.

What to wear with ankle boots – Get the Look.

I thought that ankle boots with a dress would make my feet look chunky and my legs looks shorter, and in addition I didn’t want my ankles to look wider than necessary either.

But I was wrong, and looking at the photos on Pinterest I realised that ankle boots add a lovely on-trend, fashionable slant to a daytime- dress-look.

So this autumn I know I’m most likely going to be living in my FRANKiE4 SALLis Ankle boots because they are super comfy and uber trendy and over the next few weeks I’m going to pair them with all sorts of outfits.

Check out all the styles and buy some for yourself this season at FRANKiE4 Footwear I’m finding SALLi to be the most comfortable ankle boot I own.

But let’s start with a little black dress.

What to wear with ankle boots

Ankle boots with dresses

As I said, to begin with I didn’t know which dresses to wear with ankle boots. But experimenting and pairing ankle booties with a dress was fun, and a daytime little black dress was an obvious first choice.

You might also like: Smart Casual Tips for Autumn

I think keeping the dress above your knee creates the longer line you should be aiming for, although these boots would look great with a midi-dress too (to follow).

The gorgeous tan SALLis seem to elongate my legs and because they are neutral they keep the outfit balanced – I think black boots with a little black dress might have  been just too much.

What to wear with ankle boots - the little black dress


Australian label FRANKiE4 Footwear is designed by Podiatrist and Physiotherapist, Caroline McCulloch. The stylish range boasts something called a biomechanical functional footbed. These footbeds are included with your shoe purchase to create the best custom fit, and they come in three sizes to alleviate and prevent heel and arch pain. I was gifted the SALLis in the photograph, and find them super comfy using the three quarter footbed as my feet are quite wide.  Shoes can be shipped internationally.

What outfits do you wear with ankle boots?

Do you have any tips for styling ankle boots?

Disclaimer: The SALLi boots were gifted to me. Lifestyle Fifty Website is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to If you purchase a product from one of these links it will not cost you any more, but Lifestyle Fifty may earn a small commission. Thank you for supporting my site and keeping the lights on!

Recommended Posts
Showing 4 comments
  • Kathy Marris

    Tan ankle boots are very on trend at present. I really like the look of boots with dresses. I’m looking forward to some cooler weather so that I can wear my boots!

    • Johanna

      Hey Kathy, I agree, it’s great to get back into boots in cooler weather. Once I’m into boots, I’m in them for the season 🙂

  • Life Images by Jill

    I love my ankle boots – I’ve worn them to death. But only with pants. Perhaps now it is time to break out!

    • Johanna

      Definitely time to break out and be adventurous with those ankle boots, Jill! Would love to know what you decide to pair them with.

Leave a Comment

Contact Us

We're not around right now. But you can send us an email and we'll get back to you, asap.

Start typing and press Enter to search

Fashion and Beautywhat to wear with ankle boots