Ankle boots with dresses/skirts

[Letsskidaddle]

It’s a look I love on other people but struggle with on myself. I never know what tights to wear (or not), should it be heeled boots or flat, chunky or not. If it’s tights, should they match the colour of the boots? I’d only ever wear black, brown or bare-leg and would prefer to match the boots and tights.

In the last I’ve worn knee high boots with shorter skirts.

I do prefer boots to shoes TBH, and although loafers would look good they don’t stay on my feet! I don’t want another winter wearing trousers/jeans so am hoping all you stylish ladies can advise/suggest things.

I’m 50ish, 5’1” and slim, but my legs aren’t super slim, and I don’t think this helps - the boots can be a bit tight at the ankles. Wow, I’m totally over thinking all this aren’t I 😭

I match the boots, though whether the boots are ankle boots or knee high length depends on the dress length I find.

I go for heeled boots but that's just my style and again it depends on the dress to what height of heel works.

Are you able to add a photo of one of the dresses or add a link to a similar dress?

I watched a reel about this (I know, I know) and the lady said that

• ankle boots should be worn with a skirt or dress that’s long enough so there isn’t a gap between the boot and the skirt. Is it the gap that looks awkward
• knee boots should either be with a mini/short skirt or a longer skirt. Not a knee skirt

She didn’t mention tight colour so I can’t pass on her advice there. If I wear tights in winter they’re black, I don’t have other options. I’ve not noticed any issues but with ankle boots I follow the no gap rule so you would rarely see my tights.

So ankle boots should only be work with a maxi skirt? I wear them with knee length and midi and think it looks ok

i wear heeled but flat can look nice on people with long legs!

What boots are for a knee skirt? Over the knee?

Your ankle boots are stopping at the widest part of your lower leg so it is going to make your legs look stumpy. Maybe a pointed toe or square toe boot would help elongate the foot. Have a look at Melissa Murrell for inspiration

You raise a good point 😁 According to the online stylist lady it would seem none as I don’t think she deemed a knee skirt to be something we should be wearing, but in reality I suspect lots of people will wear boots with knee skirts and look perfect.

I am chunkier of leg so for me it would have to be a knee boot as ankle boots + knee / mini skirt on me is a dreadful sight for all involved.

I only wear two types of boots with skirts. Knee high or sock boots tight around the ankle. I think ankle boots look a bit odd.

Silly and restrictive advice from "the lady" . I wear flat lace up boots, and low kitten heeled boots with skirts and dresses just below knee length to ankle length and opaque tights to match or contrast with the skirt or dress.

My calves are the widest part of my lower legs and my ankles are the narrowest! Either your ankles are unusually wide or your ankles boots are unusually tall!