Please, please help me style a Toast Bryn dress so that I don't look like a sack

[helpmestylethisdress]

In a moment of madness I bought a Toast Bryn dress. Photo attached for those unfamiliar (it isn't this exact dress but the same style). I'm not sure what possessed me, the only time I wear dresses is in 35+ degrees heat on holiday, but I have it now and I want to wear the bastard thing for a special occasion I have coming up in a few weeks. It does fit well and I think is as flattering as a dress is going to look on my lumpy, untoned size 12/14 middle aged body with zero waist (thanks HRT).

The trouble is I have no idea whatsoever how to style it, in particular shoes/boots. Toast is no help at all because they style these dresses with socks and sandals, which I am not courageous enough to even consider.

Would slightly chunky leather boots work? Can I wear tights to cover pasty legs?

I think I'll need a coat of some description. I have an oversized boiled wool coat in a similar shape to the second photo, but the fabric means it looks less formal. It would probably come to the same length as the dress though, which might be a bit awkward?

HELP ME!!!

Gah photos didn't attach

What sort of occasion is it? Don’t worry about a coat too much, as you’ll be taking it off unless the event is outdoors.

Tights and chunky boots would be fine but don’t scream special occasion. Heeled ankle boots maybe?

Is the dress that colour and pattern ?

How low does the hem fall on your legs?

Sorry I should have been more clear. It isn't a formal event - just a day out - nice lunch, museum, a bit of pottering, casual dinner. I'm just looking for a change from jeans, without feeling overdressed.

Pattern is similar, main colour is a rich olive, which is a good colour on me.

Mid shin I'd say

Navy or dark green kitten heel sling backs? With flesh tights or a bit of fake tan?

I would keep jewellery very minimum with a busy print like that.

I think it’s lovely and would work well with chunky boots and the coat. I’d add some metallic earrings in whatever colour you usually wear.

Ohhhh if you're walking a lot i'd just go for comfy shoes! Trainers even.

Nothing worse than creeping about with achy feet.

Cardigans/ jackets are quite boxy at the mo. My 3 young adult DDs wear them no longer than hip length. Nice chunky cardis but shortish.

I think the coat would look fine but be quite big to carry round a museum ect if it turns warm.

I haven't worn anything with a heel for about thirty years, I can't even imagine it any more! Good god I am suddenly realising I may be more stylistically challenged than I thought.

My usual look is casual and oversized, think Free People sweaters, barrel jeans, trainers etc?

I think what I am asking is how to style it in a way that still feels comfortable for me? If such a thing is possible?!

I often have this dilemma with dresses in winter but I think this would look great with tights and dark brown slouch boots. I know these are out of stock but I have these and they look great with most of my mid length dresses.

i always think anything looks great when worn with confidence!

Stradivarius slouchy short boot in dark brown
https://www.asos.com/stradivarius/stradivarius-slouchy-short-boot-in-dark-brown/prd/207291804#ctaref-product_share_native

I do like the boxy look, but I have broad shoulders and no waist so it is easy for me to creep into Mr Strong territory.

What length should I be aiming for do you think?

Oooo yes those are a good shout! I can imagine wearing something like that. Off to google brown slouchy boots. I can imagine getting use out of them.

Boots will be fine then.

Agree that the coat might be too warm/heavy now though. Leather jacket? Some sort of barn/chore jacket maybe?

I think in this weather, chunky boots and tights would be fine, and make it feel more casual. Could you wear a jumper over it, and take it off when you're indoors? I'm definitely a jumper rather than a cardigan person, though I'm still looking for one I like that doesn't shout 'spinster aunt' on me.

I'd also add that for me, changing what I habitually wear was really hard, because I felt overdressed. I did a lot of people-watching and tried to notice what other people were wearing, and realized no-one was going to point and laugh because I was wearing, for instance, a shirt instead of a t-shirt. It's a cute dress, and if you feel nice in it, wear it and love it!

I wear those boots with most of my dresses-they especially look good with a denim dress which I know are back in fashion. The key is to get them so they are quite slouchy and wider than your ankles so they fit the ‘casual’ look and not too dressy

Don’t wear new boots/shoes if you’ll be doing lots of walking- that way madness lies!

How about these boots? They are quite spendy but I have not bought boots for a very long time

https://www.freepeople.com/uk/shop/extra-slouch-boots/?color=020&type=REGULAR&quantity=1&size=US+8

Image of boots. I wonder if they would be an awkward length though - the hem would come to the top of the boots...

New boots with a heel for a day walking around?! Please don’t do that to yourself!

Not a fan of those brown slouchy things tbh - I’d rather have DMs.

I was just thinking the same. I would go for ankle boots personally and if doing walking I would also go for flat. I can’t walk in even the smallest heel anymore! But I know some people can

Good point! I have zero tolerance for uncomfortable footwear so would only be interested in fairly practical styles anyway. But I would be sure to break them in.