There are certain things that people find difficult to wear because they can be unflattering. Culottes, crop tops, jumpsuits….and that’s just for starters. When it comes to shoes, ankle boots can be really tricky because, as the name suggests, they cut off the slimmest part of your legs: your ankles. Flat shoes can also be troublesome, especially if you’re not tall, so combine flats and ankle boots on someone like me who’s only 5ft3? ARE YOU MAD?

Well no, actually. The older I get, the less inclined I am to stick to fashion ‘rules’ that tell me short girls shouldn’t wear midi skirts, or women over 30 should steer clear of leather trouser (nonsense!). As such, I just try stuff out and if I think it looks nice (it helps here to have an honest husband/friend whose opinion you can trust!), I go with it. And flat ankle boots are something I go with at least three times a week, especially at this time of year when it's cold.

Hannah wearing ankle boots


The key is getting the proportions right, for YOU, so experiment. On my frame, a regular ankle boot looks best with jeans, rolled up to just above the top of the boots – it gives the illusion that my legs are longer, rather than if I let my jeans hang over my boots. I find that boots that come up over my anklebone are a no-no with skirts between knee and calf-length, but with a shorter hem I can afford to go a little bit taller with my boots. But you might find that the opposite is true for you.

Once you’ve got all of that right, then comes the fun bit: SHOPPING! Ankle boots are such a classic that they’re a proper investment buy. I’ve rounded up a few more of my favourite boots on the high street…

Grenson Emma boot

Grenson Emma boots

These brown lace-ups in my video from Grenson are case in point as far as longevity is concerned. They just seem to get better with age, and I’ve swapped the laces a few times to give them an update.

Dr Martens 939 boot in grey suede

Dr Martens grey suede boots

I’ve recently fallen back in love with Dr Martens boots, having been a big fan when I was 17 back in 1994. They take a bit of wearing in but after a couple of wears they’re REALLY comfortable. A rock n roll classic.

Penelope Chilvers safari star boot

Penelope Chilvers safari boots

I have two pairs of these safari boots; the lower cut on the ankle is really flattering on me and I love all the different colour options Penelope does. Oh, and they have a crepe sole, which is just dreamy.


Office Instinct boot

Office Instinct boots

When did animal print shoes become as much of a staple as a white shirt or a Breton stripe top? Who cares, they are, and I love these from Office. Pair with that Breton and some boyfriend jeans.

Russell and Bromley Cadogan Chelsea boot

Russell and Bromley Cadogan boots

Russell and Bromely means quality shoes – these might take a little wearing in  because they’re a proper dress shoe (always wear precautionary blister plasters with new stiff shoes), but it will be worth it as they will last you for years.

& Other Stories grey leather boot

& Other Stories grey leather boots

These two-tone boots are super-chic, and feel a little more modern while still being a total classic.