Would I look like an unfashionable, 00s throwback knobhead in these bootlegs?

[MaryCondom]

I found a pair of bootleg jeans today hiding in my drawer today and I'm contemplating wearing them out in public 😱because bootlegs are back.

But the flares are quite big, and the waist is quite low-slung because these jeans are "vintage" [read: been lurking in my drawer for 20 years because I can't bear to part with them].

Does this mean I'll look like a 00s throwback loser? When people say bootlegs are back, are they these kind of bootlegs?
Or will it be obvious that I've just had these jeans for centuries and making a slightly off-kilter attempts at being fashionable?

Please be kind!

They look great. Also, they're oddly similar to the boot cuts that I'm wearing today, bought a few months back. I'm wearing a black and white plaid shirt though so what do I know.

They look great!

Love them! Plus I’m very impressed you can still wear clothes from 20 years ago! I wouldn’t fit one leg in mine these days 😂😂

I wore "vintage" bootcut jeans the other day and DD (17) complemented me on them.

I think the only way is to wear them and see how you feel. If you feel wrong wearing them out and about then put them back in the drawer.

They’re great. I’ve got some similar. They’re definitely flares, rather than bootlegs. I like to think 1970s cool hippie throwback.

Oh wow, thank you so much!

Okay, I'm going to give it a try and see how I feel out and about. They're so incredibly comfortable and I link they suit my figure which is why I've kept them for years and years. And they transport me back to my youth 😂

Now, my next question: What does someone wear on top with these kinds of jeans when that someone is a woman in her late-30s? Back in the day it'd have been a cropped vest or a velour Juicy Couture hoodie. Not sure the world is quite ready for that hot vintage mess.

I love em.

You look great and you lucky thing being able to still get into them!

I think you have a great figure and wear them well op but honestly I don’t like them. I completely accept it’s down to what I’m used to seeing though. I wore lots of low waist stuff in the 00’s and thought it looked fine but now after years of high waisted things, I think low waisted make everyone look short legged. I’m sure if low waist things come back with a vengeance my eye will change and I’ll get used to that shape again!

@Topictwenty unless you're wearing a cropped top, you can't really see where the waistline is though - if your top is coming to your hips rather than your waist (or above). To me it would be more about the feeling of a waistband that low again. And also being more careful of what underwear you wear !

Yes you’re right or course but you can see the waistband on the op’s photo and the top is pulled quite low. But that’s exactly what I mean really, wearing a top low enough to touch the top of low waisted jeans, lengthens the body and shortens the legs. The way of wearing high waisted trousers has been more about tucking tops in or wearing shorter tops which lengthens the legs loads

I've got quite long legs so I don't mind them looking a bit shorter 😂

I deliberately pulled the top up a little bit in the OP so you could see that they were low-waisted. I absolutely won't be wearing anything like crop tops with them.

And I hear the point about pants. Back in the day I used to wear thongs that'd be deliberately very visible when I moved an inch in these jeans. I shall not be doing that any time soon. Ouch.

I'm not a fan of low waist jeans as they don't sit anywhere near your actual waist. They cut you off at a much wider point. I don't like the flare it doesn't hang nicely. Your legs and figure look good but those jeans don't flatter it imo. Which is probably why you haven't worn them in twenty years and you're still unsure, if you truly loved them you'd have worn them by now.

@MaryCondom yes! The visible thongs! Wouldn't look the same with the huge 'hold it all in' pants I wear now 🤣

@Zipps I should've mentioned in my OP that they're creased to absolute shit from being in the drawer so long, so the flare doesn't sit right ATM.

I stopped wearing them when skinny jeans appeared on the scene and flares went out of fashion. I've always liked the way they look and they're super comfortable. That's why I've kept them for 20-years even though I got rid of all my other clothes from the 00s. Kept them in the hope they'd come back into fashion 😅

@ShinyAppleDreamingOfTheSea I live in women's boxer shorts these days! I now need to avoid looking like them boys from the 00s who had their Calvin Klein boxers waistband just poking out from the top of their jeans!

They’re a very similar leg shape to the two pairs I bought from ASOS last November, they were Topshop I think. I wore them with sneaker type shoes instead of heeled boots like we did back in the day so they felt more current.

They look great! I feel weird about jeans atm. Still wearing skinny jeans a lot because I have fear of the next step. Can remember going through the same process when skinny jeans came on the scene.

I am also only just getting my head into the tucking in of the tops too

Agree that they look great.

I know nothing but I can confidently state they are flares, not bootcut.

I love the colour and the fade, perfect for summer. Wear them with joy but not if there's the slightest hint of rain, and get ready to reacquaint yourself with the hipster jump, as you continually yank them up your hips!

@MorrisZapp Oh crikey, yes, I remember that hipster jump. I spent most of my teenage-hood yanking up my trousers. What a time to be alive.

@HauntedPencil I'm kind of the same about jeans. I'm not all that keen on jeans anymore. I wear black skinnies which I really like but not much else. I don't know what comes after jeans though. I tend to just live in gym gear to save making the decision.

They look fab, I would echo PP about them being flares not bootcut. In terms of what to wear them with- I'm a similar age to you, and wear mine (bought recently! And a very similar style) With graphic tshirts, striped tshirts, wide strapped vest tops, or on cooler days a jumper. They go well with converse type trainers or something like Skechers Bobs.

I think the flared leg looks very groovy and they are a good length. Need to be styled for today, maybe with some cool trainers.....so worn slightly too short with a black heeled "mum boot" peeping out may be less of a good look!

My only problem would be the low waist. Whereas I loved it at the time, it just feels so wrong not having a high waist nowadays. I'd be hitching all day. 😆

Yes I wear identical ones to those all the time!

Wear with: vest top (croppped or notbut racer cut) and oversized shirt or shacket, or chunky Cardi, or blazer.