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?

I have some Evas too. So comfortable. I wear them with trainers mostly. I am 61 so second time around for me!

The Mint Velvet ones look great. Remind me of the Gap Long and Lean ones I clung on to.

I’m 54 and wearing bootleg and wide leg just like I did in the 90s! Although now they’re higher waisted!!
Ive changed my trainers to platforms though. I’m 5’3

Have they always been called bootleg? I thought they were called bootcut, bootleg makes them sound like they are illicit
Anyway like PP I have been wearing them since the 90s and will continue to do so.

I do still wear mine with heels but also wear them with trainers and most people I see in them are in trainers. When buying them to wear with trainers, remember they need to be shorter! I have the same bootleg jeans in different lengths for this reason.

I bought two pairs of bootcut jeans from M and S the other day after years in straight ones. I have a small waist, flat stomach and slimish hips but horrible fat legs. Boot cut used to flatter my shape so I am looking forward to wearing them and hope that they still suit me! I got a black and indigo as I like to think that this is more flatteing and "slimming"!

those the ones I bought too. Quality seems amazing for the price, well made and flattering, think I will be living in them

I'm 43 and always wore bootleg. Although have Judy swapped to boyfriend as I refuse to go up size.

I've just ordered the eva bootcut from M&S and had a discount code for 15% off jeans on my sparks card so got 2 pairs for £42.50, free delivery to store tomorrow

And they do petit as I am only 5'3"

I've never stopped wearing them....

Are there any colours of denim that look more current than others?

dark indigo @Rugbyrover .

Third time around for me: 1960s/70s, 1990s and 2025! I've bought 3 pairs from M&S and wear them with heeled shoes (a bit chunky like ankle boots but without the ankle). They've always been my favourite style of trousers and they make my regular length legs look long. I still like my skinnies and wear them with flats or boots but I probably won't buy any more of those. I wouldn't be seen dead in barrel jeans - I'd look like a bandy cowboy!

I love bootcut and never gave up on them but I just bought 2 pairs of wide leg and omg it’s love they make me feel so cute (45 chubby and not been actually cute for at least 25 years)

I love my bootleg or kick flares. Don't care if they aren't in fashion or not.

Bootleg jeans are the most flattering imo. I remember reading somewhere ages ago Anna Wintour owns a pair. Not sure what brand.

I'm 62 and this is my preferred jeans style! Wear them if you like them!

Ive been in wide leg, 90s straight, bootleg, straight over the last year and bought a pair of these from eBay this week, I love them! I think they are bellbottom, but narrow at thighs, so flattering. Been wearing with a stack heel boot but tomorrow will be with chunky trainers

I’m 60 now and seem to be in the 3rd wave of wearing things…but never did and will never do rara skirts 😁

I got these M&S flares a few weeks ago and I’ve barely taken them off! They are so flattering and I’ve had compliments from more than one of the teenagers in my life, so I take that as a win! I wear them either with trainers or a low heeled pointy boot for a bit of extra leg length.
https://www.marksandspencer.com/high-waisted-crease-front-slim-flare-jeans/p/clp60643386?color=LIGHTINDIGO&_gl=11o7yttl_upMQ.._gs*MQ..&gclid=EAIaIQobChMI9ZD0sfHViwMVW6NQBh1CAQ_LEAAYASAAEgKVevD_BwE&gclsrc=aw.ds&gbraid=0AAAAAD7g6bQcznQ1uV-WrnnF4le4ETdgp

Lol drafty ! This is soo my problem ! It's a struggle 😂

I only wore bootcut jeans with flats and trainers in the 90s.

The Mint Velvet ones say do not tumble dry on the label. I never tumble dry jeans anyway though, heated airer or outside in summer.

@Justtellmewhatshappening I put another post up with a screen shot of them and the item number.