Wearing bootleg jeans second time around (now middle-aged)?

[hippospot]

I tried on some very dark indigo bootleg jeans (Mint Velvet). They fit beautifully and are so flattering.
But I have this nagging feeling about them because this is all I wore in the 90s, usually with heeled boots. I now live in flats/trainers. Would they work? I'm 50 now and can't figure out what looks good anymore... but I know I look wrong in skinnies not only because I've gained 3kg in the last 10 years.

Thoughts?

All that matters is if YOU like them. If you look good you will feel good!

All my jeans are bootleg and I’m over 50. I just need to lose a stone to get back into them.

I got a pair from next yesterday, indigo, bootleg, soft stretchy denim, after the last few years trying to feel good in skinnies or straight jeans these were like heaven, I'm having no regrets, I will mostly wear them with converse or flat adidas trainers.

I have always preferred the fit of bootleg on me. I'm 43!

I'm rejoicing, they've always looked best on me! I like a skinny thigh with a really wide flare. I'm 43 and have no concerns about them - mostly wear them with trainers.

Love a bootleg!
I'm over 50 and anything abit retro is my vibe so something like bootleg jeans, converse and a simple ringer t-shirt looks very cool IMO.😀

If they suit you, embrace and enjoy them.

57 here and just bought some... the joy :) They are just so much more flattering on me than skinnies! (worn with trainers usually)

https://mintvelvet.com/products/dark-indigo-flare
I bought these at the weekend and will be wearing them with trainers. They are really flattering

Have a look at @ phodgie on Instagram - I think they look great with trainers.

I'm in my 40s and loving bootleg and flares again. I love them with converse and trainers. I'm very glad they are now high-waisted, I definitely couldn't get away with low waisted anything these days.

Have you a link to those please?

I'm not going back. It feels too weird.

I'm in love with barrel leg now. More flattering to my shape now and more comfy and they just feel fresh and on trend.ill always feel dated in things I wore decades ago even if they come back round I either wear classic 1950s styling or I wear new shapes.

I bought 2 new pairs of bootleg jeans recently. I wear them with trainers or chunky lace ups (also 90s style!) The first time I wore them (around Christmas) they felt a bit drafty because ive only worn skinnies for the last 10 years!

I’ve always thought that bootleg jeans are the most flattering shape there is.

Are they tumble-driable please?

I’ve got the indigo Mint Velvet bootlegs and they are incredibly flattering. They look more current with trainers rather than boots I think. Waiting for a dry day to wear them!

I'm 65 and never stopped wearing bootlegs. They suit me better than any other style and I prefer the look of them. I usually wear them with chelsea boots, but that's because I live in NZ and never wear jeans in summer - if I did I would wear them with trainers. I never liked skinnies and have never owned a pair.

Did we stop wearing bootcut jeans? I never accepted the skinny jeans, skinny always looked odd to me. Just skinny legs with feet awkwardly sticking out at the bottom. I can never make it look good it's just too angular. Much prefer the way bootcut softens that leg to foot angle.
Anyway yes OP wear your bootcuts and flares and be comfy. They are the best and always have been

I still have some from the first time round and wear them with flat boots or trainers. They look better with a heel but I am 25 years older and can't be arsed.

I hang on to the pairs I love if they still look ok on me and fit. Skinny jeans are the best with knee-length boots.

I’m trying to lose weight so bought the Eva bootcut from Marks. Only £25 and so comfy and flattering. I’d stopped wearing jeans but have now bought three pairs.

@HÆLTHEPAIN they were in the sale/clearance section but I only got them this week, I've tried to add a picture although they are darker than the picture, next sale online is not always accurate

I think you get to an age where you have worn all the styles at least twice.
DON'T PANIC
Wear the bootlegs, team them up with you appropriate other stuff and relax.

They are gorgeous!

I'm mid 50s and have now embraced the bootleg. I always thought skinny jeans looked odd with chunky trainers.

I always thought skinny jeans looked odd with chunky trainers.
They look strange if you have long feet.