What to wear with bootleg jeans?

[ThisIsBanana5]

I recently dug my bootlegs out of the back of the wardrobe which I haven't worn for about 5 years.
Wore a pair today with chelsea boots and a jumper but felt a bit frumpy. I'm not sure they would look right with trainers? They're not long enough to wear with heels and I do too much walking for uncomfortable shoes... I used to absolutely love that look though.
It might be that I'm just so used to myself in skinnies I need to get used to the change. Any ideas, tips etc for styling bootleg jeans with flat shoes would be gratefully received!
Thanks!

Bump

Is "boots" too obvious?

I wear mine with trainers but I'm not much of a fashion guide. Loafers should work also.

Just to add, I really like wearing bootcut jeans with a blazer, it seems to balance out the silhouette nicely.

I wore mine last night with trainers and a big slouchy jumper... but I don't think I got it right tbh.

Last year it was all tucked in tops or shirts with big belts and heeled boots. But that somehow feels dated already to me? But maybe I'm being too picky.

I think, for me, the problem might be that I remember them from the late nineties and early noughties, so it's difficult to style them without feeling as if I'm reverting to a very old style!

How about a low platform trainer?

Thanks all. @CamilleCamisole yes, I think that is my problem too.

Blazer is a good shout, will also try my loafers and not rule out trainers. Bootcut is definitely a flattering shape on me as I'm a pear so I will keep trying and hopefully find a winning combination.

I'm wearing mine today with a striped jumper and leather Converse, plus a leather jacket.

Yesterday I wore them with Converse, a fluffy grey jumper and a long checked grey coat.

I wear mine with carvela trainers. But more dressy than casual trainers. Fitted jumper on top.

Cowboy boots here!

What do you think of today's lower half? Sorry, too paranoid to show any more but hopefully this gives an idea.

I think your jeans may be a wee bit too big for you? Or maybe you need bigger heels with them.

Again though, I might be being too picky about the wole bootcut Jean thing!

I agree that they're a bit too long for those boots.

*whole bootcut jean thing

Yeah sorry, they are a touch too long for those boots

Interesting. Those boots are completely flat. Will try some low heels.

Cuban heel cowboy boots, they always look right with bootcut. The hint is in the name...

I hate that they are back. I’m such a fashion victim that I will no doubt be wearing them again soon.

This is why I don’t think bootlegs will take off in any big way, too much faff on which boot or shoe works with them. I think you need to get some current boot leg jeans rather than ones you had back in the day, yours do look frumpy to me, they look neither one thing or the other, when a fashion comes round again there is always a subtle difference that makes them look current and I think yours do miss the mark.

Just remembered that mine are slim flares, rather than boot cuts.

What sort of cowboy boots do people have? I've got some Ash things that I call my gunslinger boots, but they are not very comfortable.

@AmberLynn1536

This is why I don’t think bootlegs will take off in any big way, too much faff on which boot or shoe works with them. I think you need to get some current boot leg jeans rather than ones you had back in the day, yours do look frumpy to me, they look neither one thing or the other, when a fashion comes round again there is always a subtle difference that makes them look current and I think yours do miss the mark.

To be honest I don't think I ever particularly liked these ones, a couple of other pairs I have were much nicer but everything spread out after having a baby and they don't do up any more. Looking at the photo these are oddly baggy round the knees.

Personally I think the more contemporary bootcut jean would be a bit shorter in the leg and finish neatly with no excess material around the ankle. Having the bottoms dragging on the floor is a bit 90's - sorry.
A bit shorter with platform trainers or like someone else said maybe cowboy boots or similar.
Wide leg jeans would be a more modern look than bootcut imo.

Em, they’re dead old fashioned, sorry. I see one school mum wearing these and I always think, Jeez, haven’t you bought yourself any new clothes in the last 20 years? But she also has a feathered mullet and frosted tips, so maybe she’s just really devoted to her personal style.

They look very dated to me, sorry. What do I know though.

RSoles have provided me with my stash of wonderful cowboy boots (some are from ebay and some from the R Soles website). I have 10 pairs, amassed over 20 years!

I bought some black bootcut Jean's recently but they are more skinny flares and I love them.