How to style midi/maxi dresses for autumn/winter

[SRK16]

I’ve been living in midi dresses this summer, usually with sandals. When I look online I can see them styles with boots for autumn, but when I try it it looks ridiculous. I think because the boots maybe come up too high on the ankle so my legs end up looking stumpy?
Does anyone have ideas of boots or shoes I could use with this look?
I’m 5’5, size 14 (though currently 38 weeks pregnant!) and have big boobs.
Would black tights be a total no go? I want to look good but also don’t want to freeze!
Or do I just pack the dresses away til spring :(

[BoogleMcGroogle]

I'm going for tights and long boots, modelling myself on a young Meg Ryan or Anne Diamond on the TV-AM sofa circa 1985. It's not fashionable but it's flattering and, crucially, warm.

[RacheyCat]

I wear my maxi dresses with socks and birkenstocks at this time of year, and I'm not even sorry.

[AbandonHopeDarr3n]

How about trainers or brogues?

At least you won't be pregnant much longer, so you may want to wear something different soon anyway. If you're planning on bfing especially.

Re tights; I think it depends on the dress. A midi dress with black tights and brogues sounds pretty standard to me though.

[Oly4]

I agree that boots and dresses look awful on me! I’m going to try trainers

[DontCallMeShitley]

Doc Martens. So many to choose from, different heights, but the lace up ones not the other styles.

[AbandonHopeDarr3n]

Oh yeah, good shout with the DMs! I am getting some for next birthday. Quite possibly from myself...

[Shitonthebloodything]

I'm planning on wearing mine lots with tights and ankle boots or biker boots. I wore a rusty red coloured midi dress with tan ankle boots and black tights and it looked fine. Midis do come up long on me though so more like a short maxi.

[Annasgirl]

I wear mine with trainers and a leather jacket.

I agree boots don't look as good IRL as on fashion shoots (what does?) but I am going to try out the DMs for later in Autumn. Also brogues or flatform brogues look good if you don't like the look of boots.

[Ellapaella]

Definitely DM's. I've a cherry red pair that I'm wearing with my dresses. Adding a chunky knit cardigan on colder days.

[SRK16]

Feel like I can’t pull off DM’s but maybe I should try? I think I’m stuck in a winter shoe rut which is part of the problem, I basically only wear chunky Chelsea boots and feel everything else looks weird!

[Headinthedrawer]

I came on here to ask the same question!Ellapaella I bought the New look chiffon maxi dress after seeing your photo the other day...I love it.But if I buy the cherry reds too I'll be totally wearing your style!I have bought some ankle boots from Clarke's.Quite a heel but super comfy.Called Verona Trish in tan.Look.great with everything.But I'm also getting Dms for my birthday.Feels too hot for boots and too cold for sandals now though so I'm going to try my white Hush pumps.

[Softpebbles]

Ha - I went to try that new look Dress on too but it was out of stock in my size!

I do have doc martens too!

[Ellapaella]

DM's go with absolutely everything so I'd give them a try. They have been my favourite buy this year.
@Headinthedrawer definitely wear the DM's with the New Look dress, they go really well together. It's unlikely we will be bumping into each other in our matching outfits very soon but if we do I'll give you a high five 🖐

[EmmaStone]

Trainers and a leather or denim jacket for me.

As it gets cooler, I might go tights and ankle boots. I find the most flattering have a bit of a V shape at the front of the ankle, stops legs looking stumpy (eg Ash Jalouse style).

[RemusLupinsBiggestGroupie]

I wear mine with fishnets and white trainers, or fishnets and ankle boots (although heeled ones look better than flats, but I wear flats sometimes anyway). I prefer fishnets to opaques, unless it's really cold. Opaques don't work with trainers, or not with my white ones anyway.

[NiteFlights]

Midi is much easier to wear in winter than maxi imo. Chelsea boots cut off your leg in the wrong place and make your legs look stumpy. Knee boots are great with midi dresses but if you want ankle boots they have to have the v or lower cut at the front, as EmmaStone said.

DMs are classic, strangely flattering, practical, go with pretty much everything and last for years. They are quite heavy though so it depends whether you like that feeling.

I am shorter than you but I don’t wear long skirts in the winter as it’s just too much hassle to cope with boots and coat lengths.