Ankle boots + Dresses?

[Deianira]

It's raining, and this has once again brought home to me my lack of suitable autumn/winter footwear. So, please talk to me about ankle boots! My dilemma is that I wear quite a lot of dresses, especially for work, of a smart/casual style (less smart than 'workwear', not slobby) mostly around knee-length, and I can never work out what boots will work with this.

I have some slouchy short (mid-shin-ish) boots both with a heel and without which work with trousers/jeans, but they are too short for wearing with dresses, the gap between skirt and boot is somehow odd looking. Full knee boots intimidate me and are expensive, so I'm wondering whether it's actually possible to wear ankle boots with a dress, or whether this will just look wrong? And if it is possible, does anyone have any recommendations?

If you think this is absolutely a non-starter, then I'd also appreciate recommendations for any longer boots which are not too pricey and you think would work with pretty much any style of dress. Somehow I am just not good at working out how to buy boots!

I always wear Chelsea boots with dresses, and I don't think it looks weird. I see plenty of other people wearing ankle boots with dresses too. Is it not just that you're not used to seeing it on yourself so it looks strange?

I think knee-length dresses will look fine with some types of ankle boots. They need to be close-fitting at the ankle, not the sort you could tuck jeans into. I've just bought these: www.flickr.com/photos/32541343@N00/20811368242/sizes/m/ and was wearing them with a short dress and black semi-opaques yesterday and I thought that worked quite well, I've also had black lace-up "granny boots" in the past and I like those with skirts and dresses. If I have to wear a skirt with short boots with wider tops, I feel like they need legwarmers or something to fill in the gap, and that wouldn't be as work-friendly.

I wear Chelsea boots with tube skirts, but don't think they work with anything with 'flounce' of any sort. For those, I wear heeled ankle boots or knee high boots.

Then again, Chelsea boots look lovely with little 'flouncy' dresses on my skinny, tall dd1!

Another vote for Chelsea boots. What can so work is mid calf slouch style boots with a small heel.

I wear heeled Chelsea boot style ankle boots with skirts and dresses for work. I think they look ok and I've been complimented on them before. Try a few?!

I always wear ankle boots & dresses in autumn and winter. I like fitted lace up ones with a small chunky heel.

I wear ankle boots with dresses and skirts. I have worn them for half of this summer! Much prefer boots to shoes anyway.

FelixFelix I think it's partly that, yes - I'm not used to them so they seem odd. But not entirely - I do think the boots have to be quite carefully chosen, which is why I am grateful for suggestions on styles!

Thanks for the suggestions so far - I do tend towards the fuller/flouncier skirt, which I think is why I've been getting stuck. I worry that a lot of ankle boots are too much of a contrast with that, if that makes sense? Chelsea boots are one of those I think seem a bit blunt/hard-looking in comparison to the style of dress, but maybe that's just me!

I have some like that jellyjiggles and like them a lot, but as I say, the length means they work for some of my dresses but look weird with others, hence exploring other options! I think that EmmaWoodlouse you're right that something close-fitting at the ankle is probably better, and probably some heel is a good idea - although I am very tall, so too much heel doesn't work! I was wondering about some in this sort of style: Dune Boots but can't decide!

I think unless you have very long legs, it looks best to have either your knees or ankles visible. So I'd wear dresses that come to just above the knee or shorter with ankle boots.

m.gap.co.uk/product.html?dn=gp000534141000&dv=1&sdkw=leather-chelsea-booties-P000534141&kwid=1&referrer=http%3A%2F%2Fwww.gap.co.uk%2Fproducts%2Fleather-chelsea-booties-P000534141.jsp%3Fpid%3D000534141000%26vid%3D1&sdReferer=http%3A%2F%2Fwww.gap.co.uk%2Fproducts%2Fwomens-shoes.jsp&pid=000534141000&sem=false&vid=1&preferredLocale=en_GB

These are quite dainty and would work with dresses imo

ankle cowgirl boots look great with fuller skirted knee length dresses.

These are more flattering on the ankle www.pikolinos.com/uk-en/lille-905-7522.html?cl=BLACK

I quite like these www.pikolinos.com/uk-en/salerno-w9c-4519.html?cl=LEAD

I wear these with dresses and/or skinny jeans - also have you considered peep toe shoe-boots? They're not for everyone, but I live in mine (a very plain black leather pair from Whistles last year) and wear with or without tights underneath.

I wear ankle/calf boots with dresses all the time. I have some black suede ones with a block heel which are ancient and will probably need to be replaced this winter, and a couple of more biker-type ones which are flat. I think they look good with opaque tights and a dress.

The main problem I have with boots is a very high instep and less-then-slender ankles so getting a decent fit is usually a struggle. I've lost count of the pairs of boots I've had to return.

Here are the Whistles pair - and they're in the SALE!! So comfy and easy to walk in too www.whistles.com/women/sale/shoes/ania-open-toe-boot-17456.html

LOVE the Whistles ones. I have these Whistles ones but have only worn them with jeans so far. The Ash are v nice, but a lot of money for a style that can be found all over the high street for much less.

Don't like any of the others posted so far, sorry.

Yeah the Ash ones were £££ compared to high st, but so soft and comfy and haven't gone funny when rained on like suede can do.

I read somewhere once that a dip in the front of the ankle part of the boots elongates and makes your legs look longer? Like these Rag&Bone ones (ignore the price tag there are tons of high st copies out there)

Ooh I like these although they will probably be seen as, 'Mum boots' on here.

I wear Chelsea boots with dresses and opaques all the time, and also black biker boots. My dresses aren't especially flouncy, but I do have some skater styles, and they look good. I think the contrast with fussy florals - which aren't my thing anyway - can sometimes jar a bit, but they are great with more graphic prints. My skirts tend to end a couple of inches above my knee.

How opaque would you suggest the tights be? I'm wearing a shortish dress with ankle boots tomorrow and I think my 100 denier tights are a too dark, but the dress is a little too short for sheer tights or bare legs.

Thanks a lot for all the suggestions - I have plenty of ideas to try now! The Whistles ones look especially fantastic, Glitterspy, but probably not what I should be getting given that I was meant to be finding some sensible things to keep my feet dry!

Love those boots Remus