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Original poster

Just bought this dress and wondering if I am brave enough to wear it with ankle boots...

44 replies

JessiCake · 26/09/2017 13:14

... for an evening do tomorrow.

www.whistles.com/women/clothing/dresses/lola-dress-26912.html?dwvar_lola-dress-26912_color=Black#start=1

I am in love with the dress itself, IT HAS POCKETS, I repeat, it has POCKETS!! Flattering cut and length on me, the fabric (although is viscose) feels lovely and light.

In the pic they have put it with ankle boots; I have never worn a dress with ankle boots before and am worried I can't pull it off. Also the only ankle boots I have (which are nice in themselves and barely worn yet) are tan. I think style-wise they will work (they have a low-ish Cuban heel and are a slightly Western style) but is tan and black ok? Tan doesn't feel very 'evening' ish either but it's a casual do and the dress is obviously a casual style so wouldn't look right very styled 'up'.

In the pic they do leopard print which isn't one I would go for (plus after buying the dress I can't afford new boots!!)

But at 40, can I pull off the dress with ankle boots look?! I'm not as skinny as the model in the pic (or as gorgeous... or as young...) though I am a size 10 and my legs are decent.

I can play it safe with a ballet flat (I have some quite nice leopard ones).

I haven't even tried the ankle boots on with the dress yet as I'm so scared of looking so utterly silly... Blush

OP posts:
Original poster
JessiCake · 26/09/2017 13:15

Oh I should add - not just being a sheep - as I walked home from buying the dress I was pondering an ankle boot and then went online to see what they had put it with there...

OP posts:
PolkadottyRose · 26/09/2017 13:19

Please do wear it with ankle boots! I bought ankle boots a few years ago specifically because I wanted to wear them with dresses. I feel no shame at that, they look nice!

PurpleWithRed · 26/09/2017 13:19

I am also currently wobbling over taking the Ankle Boot plunge. Rationally , everyone does it so it must be OK. Emotionally - it’s so YOUNG and NOW and I know my mum would be wierded out (she is 97).

Great dress by the way.

CremeDeSudo · 26/09/2017 13:27

Should we feel shame at wearing ankle boots and dresses? I only ever wear ankle boots when I wear a dress!

Love this dress and think it would look awesome with tan ankle boots!

Original poster
JessiCake · 26/09/2017 13:34

Ah thank you for the reassurance everyone!

I now feel emboldened enough to go and try it on...

I'm assuming bare legs are needed...?

No shame AT ALL in this look Creme, I adore it on other people and have long wanted to give it a go myself but like Purple says above, I fear looking too YOUNG and NOW (and actually my mum would be utterly appalled by the look, too, she has hissy fits when people wear skirts with trainers...)

It's a fab dress isn't it, I have treated myself. Just getting into dresses now as I get older (and after having lost some weight) and this is the style I have found that just works for me. The sleeve length is divine too, fractionally below elbow on me.

Thanks so much everyone!

OP posts:
Maudlinmaud · 26/09/2017 13:35

I've been wearing ankle boots with dresses for the past few seasons. I didn't know it was risqué. I have a lot of ankle boots, I mean a lot.
I like your dress. Now how evening is evening? Is it fancy schmancy?

MaudesMum · 26/09/2017 13:38

I'd probably wear it with thinnish black opaques at this time of year. Great dress!!

PolkadottyRose · 26/09/2017 13:39

I didn't literally mean it was shameful, my apologies..I just meant that I didn't care what it was or wasn't because I like wearing them like that.

Original poster
JessiCake · 26/09/2017 13:39

Maudlin, no no dont' get me wrong, it's not remotely risque, it's such an awesome look that I have yearned after it for a while... but it is a very 'modern' look if that makes sense - 10 years ago (which is roughly when I was last able to take a proper interest in fashion...) it wasn't around, I don't think. Iit's a terrific look as it mixes things up and proportion wise I think it looks excellent.

Evening is... evening-ish. It's not fancy-schmancy but I want to look as if I've made an effort. I don't think anyone else will be wearing jeans, for example (unless quite glitzed up) but a traditional LBD and heels would be too 'much', for sure.

OP posts:
Original poster
JessiCake · 26/09/2017 13:41

Will try it with think opaques and bare legs - I'd probably be slightly more comfortable in opaques tbh but as it's an evening do and there will be fairly dim lighting (I think!) I could definitely try bare legs, I have perfected a Sally Hansen trick after advice on here that worked throughout the summer...

OP posts:
Mosaic123 · 26/09/2017 13:41

You could add a nice long gold pendant or big earrings. The gold will go with the tan of the boots.

Original poster
JessiCake · 26/09/2017 13:43

Mosaic, great minds, I do in fact have a long gold pendant and was thinking that might work... I love gold with black anyway and yes it would tie in the tan...

OP posts:
rightknockered · 26/09/2017 13:44

I'm 40+ and have a dress like that which I wear with trainers and ankle boots. (I even have the exact boots in that pic Grin) The only thing to do it put the boots on with the dress. You'll get used to it after a while. Try them on and wear them about the house so that it feels normal to you. I promise you'll look fab x

rightknockered · 26/09/2017 13:46

I would wear thin opaques and glitzy earrings

Original poster
JessiCake · 26/09/2017 13:48

Thank you rightknockered, I will have a swoossh about the house in it all this evening... Grin

I wore a similar dress (more casual, stripey) in the summer with trainers and felt fab in it. I think that cocooon style is at its absolute best with a casual shoe/boot on the bottom.

OP posts:
Original poster
JessiCake · 26/09/2017 13:49

Thin opqaues being... what, around 30 denier ish...? 40...? I tend to go for a very very thick matte denier when I wear shorter skirts/more formal outfits but that would be too heavy for this dress I think.

OP posts:
CoffeeCupCake · 26/09/2017 13:49

I think tan and black will look nice. Not sure about tights vs bare legs... I think opaques might be too much black, do you have any patterned tights (still black but with a design, hopefully you know the type I mean!?!)?
Enjoy the event Smile

CoffeeCupCake · 26/09/2017 13:51

Ah, cross post. Yep, I think 30 or 40 would work well, actually. Try it on (and let us know!).

Original poster
JessiCake · 26/09/2017 13:52

Coffee, thank you - I do have some much-loved micro-net fishnets that I wore a lot last winter when I was in a pencil-skirt-and-sweater phase. But I know fishnets can give the wrong impression (and this is a do with new-ish colleagues so I don't want to do that!!) I personally adore a fishnet but I don't want to send out the wrong signals iyswim...?

OP posts:
CoffeeCupCake · 26/09/2017 14:00

Micro fishnets would look good. If they're really small 'holes' I wouldn't think they were too racy, worth a try at least!
Otherwise, maybe something like these: Link

Original poster
JessiCake · 26/09/2017 14:02

Oh, wow, yes I love those linked ones, thank you so much!! Will pop to H and M tomorrow morning, don't have time to order them for tomorrow night unfortunately. Those would be great, I think.

OP posts:
Fightthebear · 26/09/2017 14:07

I've got that dress (lovely). I wear it with opaque tights and black ankle boots because it's too short on me for bare legs.

Fightthebear · 26/09/2017 14:08

Ps. Of course 40 is not too old for the dress/ankle boot look, it's a new classic.

CoffeeCupCake · 26/09/2017 14:16

You're welcome!

Peppermeant · 26/09/2017 14:18

Apart from ankle boots, I can't actually imagine what else you would wear with this dress! Heels wouldn't look right and trainers too casual. I don't think ballet flats would work either?