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should i buy pointy boots again having worn them in the noughties?

21 replies

theredlynx · 06/10/2026 22:58

i'm contemplating buying myself some pointed toe boots for work but i feel a bit funny about it because i've kind of already had a pointy boot phase back in the noughties. I was the same with doc martens i wore them in the nineties as a teenager and wasnt going to go there until my daughter got given a pair which were too small so i started wearing them and loved them. anyone else going through those boot trends for the second time?

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lavendarwillow · 06/10/2026 23:03

I think if you wear wide leg trousers and want to wear boots, pointy ones look way better than round toe.

theredlynx · 06/10/2026 23:09

lavendarwillow · 06/10/2026 23:03

I think if you wear wide leg trousers and want to wear boots, pointy ones look way better than round toe.

yes i think you are completely right, just not sure if i'm too old in my late forties for them. I'd wear them with dresses and long skirts too

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seahorsessky · 06/10/2026 23:10

Yes, if you like them, and have no foot issues (sometimes a trend doesn't work for people second time round if their body has changed, like you used to wear high heels, but have worn nothing but trainers for 15 years and heels hurt!)

Bonus points if you've still got your 00s stuff.

DramaAlpaca · 06/10/2026 23:12

Well they seem to be back in, so if you like them go for it.

For me, I've decided that I won't do pointy shoes this time around because I'm no longer keen on having my toes squished.

theredlynx · 06/10/2026 23:13

seahorsessky · 06/10/2026 23:10

Yes, if you like them, and have no foot issues (sometimes a trend doesn't work for people second time round if their body has changed, like you used to wear high heels, but have worn nothing but trainers for 15 years and heels hurt!)

Bonus points if you've still got your 00s stuff.

i do still have a dark brown pair which is handy! i've worn cowboy boots for a while so am used to the pointy toe but not a stiletto heel. but i dont think i can wear cowboy boots to work

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theredlynx · 06/10/2026 23:15

DramaAlpaca · 06/10/2026 23:12

Well they seem to be back in, so if you like them go for it.

For me, I've decided that I won't do pointy shoes this time around because I'm no longer keen on having my toes squished.

i'm probably lucky I dont have too much problem with my toes, i wear cowboy boots with a pointed toe. Heels not so good but im sat down most of the day at work. it just feels a bit weird wearing something that i wore when i was in my late twenties

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Melancholyflower · 06/10/2026 23:24

Well there aren't that many different toe shapes that boots can have, so I would think it would be inevitable that you would re-visit a shape you have worn in the past.

Gettingbysomehow · 07/10/2026 07:17

theredlynx · 06/10/2026 23:09

yes i think you are completely right, just not sure if i'm too old in my late forties for them. I'd wear them with dresses and long skirts too

I wear them with kick flare trousers and Im 64.

Gettingbysomehow · 07/10/2026 07:18

So long as they dont make you look like Cotton eye Jo they are fine 😅

NoWeaponsOnTheTable · 07/10/2026 07:20

Love a pointy toe!
I never stopped wearing them and I'm nearly 50.
I don't care if I'm fashionable or not, wear what you want and is comfortable!

mynameiscalypso · 07/10/2026 07:24

I wear pointy toe boots (albeit with a block heel) as I generally wear wide leg trousers to work and I agree with a PP that they look much better. I size up and wear thick socks generally so they’re more comfy than the ones I shoved my feet into 20 years ago.

LlamasDramas · 07/10/2026 07:24

No! They crush your toes or you have to buy a very long pair so they don't put pressure on your feet.

Wore them in the 80s - Lady Diana really was instrumental in making them so fashionable. Pointed shoes with bows were everywhere. Pointed boots came fashionable later if I remember rightly.

Anyway, wearing my much loved pointed shoes forever deformed my feet. It made my toes sort of more curved and you can almost trace a triangular line where they were crushed. Wear them at your peril!

ZenNudist · 07/10/2026 07:25

I feel the same about boot cut jeans and the 00s.

Floisme · 07/10/2026 07:38

I’m wearing some styles for the third time. Fashion is circular and very few looks are new but a lot of us are in our 40s or 50s before this hits home. You can either give up on fashion or get over it.

CortieTat · 07/10/2026 07:57

They have been back for quite some time so you can safely wear them :-)

I never wore them first time around when I was a teenager, never liked the look.

TheCabbageMerchant · 07/10/2026 09:44

NoWeaponsOnTheTable · 07/10/2026 07:20

Love a pointy toe!
I never stopped wearing them and I'm nearly 50.
I don't care if I'm fashionable or not, wear what you want and is comfortable!

Basically this!

theredlynx · 07/10/2026 10:00

NoWeaponsOnTheTable · 07/10/2026 07:20

Love a pointy toe!
I never stopped wearing them and I'm nearly 50.
I don't care if I'm fashionable or not, wear what you want and is comfortable!

good to hear. i will do it! i loved them first time round. i went through three pairs. i think of all the shoes and boots they are the one that have given me a bit of confidence

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theredlynx · 07/10/2026 10:01

Floisme · 07/10/2026 07:38

I’m wearing some styles for the third time. Fashion is circular and very few looks are new but a lot of us are in our 40s or 50s before this hits home. You can either give up on fashion or get over it.

good point, wish i had thrown a lot less out!

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lindyloo57 · 07/10/2026 18:44

I just wish my toes would let me wear them,

EmotionallyUnavailableGuacamole · 07/10/2026 22:54

I didn’t know I was supposed to have stopped wearing them!

theredlynx · 07/10/2026 23:03

EmotionallyUnavailableGuacamole · 07/10/2026 22:54

I didn’t know I was supposed to have stopped wearing them!

good point! you cant beat them in terms of a boot that looks equally chic at work and for a night out

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