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Fashion advice for dating again at 49!

8 replies

Didion · 04/08/2026 19:57

I would be very grateful for any advice and guidance, please.

I'm 49 and have totally lost my way fashion-wise. I'm about to start dating after many years in an unhappy relationship and then as a single person, but with so many caring responsibilities that I didn't even think about men!

So, I live in frumpy supermarket clothes and desperately need a fashion glow-up!

I'm 5ft 5" and am 11 stones, but hoping to lose at least one more stone (currently on Mounjaro).

I'm a C cup, so low-cut things don't tend to work on me. Sadly tree trunk thighs!

What do you advise I wear for everyday and going out, that makes me look better than the sack of spuds that I currently look like? My budget is relatively modest, I think.

Thank you everyone.

OP posts:
SaraHoliday · 04/08/2026 23:57

Have a look at Melissa Morrell on YouTube. She styles a lot of body shapes and gives good advice.

- YouTube

Enjoy the videos and music that you love, upload original content and share it all with friends, family and the world on YouTube.

https://youtu.be/KlGlVvIrS7Y?si=S6pFt7CXDVRZfSDy

NorWouldTilly · 05/08/2026 12:36

So … what sort of styles have you found yourself admiring in the past?

And do you want your new wardrobe to be purely functional, or to project something of your personality? D’you think you’re more:

Cos
Toast
Zara

for instance?

Lavagirl · 22/09/2026 09:01

A short message in solidarity - also 49 and dating! I take tips from my teenage daughters who are super savvy about makeup, skincare, fashion etc and they assure me that what we used to think of as problematic 'tree trunk thighs' are now highly valued 'thicc' legs, which men love. I'm currently dating a man 10 times younger than me, gorgeous, loves the bum and legs that I've spent a lifetime resenting. What an absolute revelation! Buy everything on Vinted and never be afraid of making bold choices. Enjoy xx

MakemineaGandT · 22/09/2026 09:51

As a starting point, what do you already have that makes you feel good? Like a great version of yourself? You’ll be more relaxed on your date if you feel like the best version of yourself, not ‘dressing up’ - it’s not the time to try new styles. If you give us some clues as to your preferences we might be able to make better suggestions

madaboutpurple · 22/09/2026 09:53

I agree with Lavagirl as you will be able to get good quality clothes on Vinted and they won't break the bank.

baloonsrising · 22/09/2026 10:50

Lavagirl · 22/09/2026 09:01

A short message in solidarity - also 49 and dating! I take tips from my teenage daughters who are super savvy about makeup, skincare, fashion etc and they assure me that what we used to think of as problematic 'tree trunk thighs' are now highly valued 'thicc' legs, which men love. I'm currently dating a man 10 times younger than me, gorgeous, loves the bum and legs that I've spent a lifetime resenting. What an absolute revelation! Buy everything on Vinted and never be afraid of making bold choices. Enjoy xx

Hopefully he's not 10X younger than you :)

NorWouldTilly · 22/09/2026 10:56

Oh … @Didion never came back?

I never learn … 🙄

Lavagirl · 22/09/2026 13:15

oops! I meant 10 years, not 10 times younger!!! That'd be weird...

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