It’s all fine if you are thin and flat from crotch to waist

I wear a knit top (turtleneck, tee or sweater) and a blazer with scarf when I wear my boot cut jeans. But I love the look of my button downs too but add a belt with it then. On my feet I usually wear boots (heeled or wedge) except when volunteering when I need to wear trainers/walkers. (I actually have the #2 shoe of Christina's post- just never had occasion to wear them with jeans-just dress pants- but I will now!)
So I am opposite- I have no problem with boot cut but I am just not happy with my skinny jeans- I think I need to do some hunting.

Hey Lisa, I bought a couple pairs of flares a couple of years ago for variety and I love them. However, they don't get worn very much because of weather (pant hems touching the ground is tricky in Toronto weather.) Haven't gotten into boot cuts because they still remind me of Britney Spears and the Gilmore girls... But my eye is adjusting agreed that they are likely better for me too.

I find that flares can make you look like a tall glass of water - as long as you get the proportions right. On me (petite and curvy, as far from tall and lean as you can get) I find a top that is a fluid or structured, not too drapey that hits mid hip is ideal. If it hits any longer than that I look dumpy. Also a blazer or vest on to is crucial as it makes the line long and lean.

A couple of options:
Have you thought of a long vest or gilet? Coupled with the right fluid top, I find that they pair with flares to make you look long and lean (also they hide the hips nicely.) See attached on me - you wouldn't have to tuck in the top.

Another look that works for me and that is modern is flares paired with a to that hits mid hip (fluid or structured) and a cocoon cardigan (not too much volume.)

Attached are a couple of photos. I have tucked in tops here but you could easily leave them out. I pair with pointy heels or platforms for a long leg line.

I have one pair - I thin mine are flares rather then bootcuts - but not true bell bottoms.

I think a jacket or kimono or gilet over a mire fitted top is a great flattering look. But there have been lots of fun looks posted.

I would be tempted to buy a pair from a place you know you can return- and play around. If you can get three looks you like then keep them.

I got mine in spring and have probably worn 8 times - mostly with tee type tops and always with mid heels. I liked mine with boots but not my sandal boots - and I liked them with sandals.

It is the mix up that I enjoy- a change. And I think they work for drinks with girlfriends, work and outings. I can't wear to dinner at friends because they don't work for houses with shoes off policies!!

https://shop.nordstrom.com/s/c.....tcut-jeans
Peplum to short as our pants but you get the idea. It's proportional.

https://youlookfab.com/2013/03.....vy-figures Again a smidge longer but it's a a very elegant slimming look

https://www.pinterest.com/pin/281967626643624379 I can't find this with bootcuts but can you do shirt with sweater over to create a layered look? Try curved him on shirt tail, also the combo shirt sweaters for less bulk. Again proportion will be key but look how uber flattering

https://www.lilacandlipgloss.c.....cd2b5842c/ Ok too boho and I think bootcuts need less scoop for proportion but length on top was good.

https://www.pinterest.com/bash.....s/?lp=true Pay dirt! I like the shirt with cropped sweater. Lots of no visible crotch point outfits. some great fluid tops and blazer combos. I thought this page had a lot of outfits that looked like "you." Hope this helps!!

Well, I grew up in the era (late 90s) when tapered pants were the un-coolest, and all pants had to flare at the bottom, so I'm a forever-fan of bootcuts, flares, bellbottoms and wide-legs. Really I love it all (also I have large calves relative to the rest of me, so pants that widen at the bottom are much easier for me to fit and wear). I only have one pair of bootcuts (vintage Red Engine, magically perfect mid-rise fit), which are dangerously close to threadbare on the seat, and I would love to find a replacement. I almost always wear mine with lace-up boots and a chunky sweater of some sort, or blazer-over-tee. Some volume on top, whether it's sweater or a big scarf or whatever, helps these work for my eye, but that may also be body type dependent.

Things I don't wear with bootcuts: western/cowboy boots, boho/platform sandals, plaid/flannel shirts, chambray shirts. All of these veer a little to literal for me -- I want some juxtaposition rather than a solid column of "western, or 70s- inspired" you know? What I see on others and like, but don't have the elements to do it myself: white sneakers and a bomber jacket; longer tunics (or dresses as tunics, like Diana shows) especially the sleek black sort in the blog gryffin links to, and long vests/gilets like Roxanna suggests. I mean -- if you're wearing cropped flares and like the look, I see no reason why you couldn't make a full-length flare work.

The blouse-y tops cover the "crotch the waist" area! It's a good idea, and a pretty "boho-lite" look.

Lisa p, I like my bell bottom hems looooooonnnnng. Floor skimming. So you don't see the heel of the shoes. Any type of heel will work. I like pointy toes though. They peek out well from under a wide hem.

Angie - I agree with the length. The pair I'll be experimenting with is not quite floor skimming, as they aren't a true bell bottom, but we'll see how it goes. Thank you for chiming back in.

LaP - I agree with needing juxtaposition - and I would NEVER wear anything western in look. I am quite positive about that one My version is not having the look read too boho anymore - I'd like this to be a work look. Or - as you suggest, a chunky sweater and boots - great for weekends.

gryffin - thank you again ! It all looks so easy, doesn't it ? No shirt under sweaters for me (not my style, plus doesn't suit my body type) though. I'm going to try your first suggestions of a blazer and loose fit top of some kind. I'll post something on Monday, hopefully!

Sally - aha - lightbulb moment - a kimono is a great idea, and I've always wanted one . Thank you!

Roxanna - good ideas, both. And yes, laughing at the Gilmore Girls reference. Flares are the way to go, not bootcuts, I agree. I think I am using the term bootcut to refer to anything not-straight. But there is a big difference between flared and bootcut, isn't there? And I agree with how leg-lengthening and height accentuating they can be, and that's exactly why I am interested in trying them again. I hate the way I look in long vests ( I have 3 and never wear them - I think it's the short hair issue = too pin-head ish) but yes to a fluid top and jacket.

I'm in the loose top, structured long blazer camp. Blazer should have sharp shoulders. And -- the flare needs a higher heel.

I have a pair of super wide bell bottoms from a few years ago when flares made another blip on the fashion screen. I wore them with a longer loose top and shorter blazer of the same color as the top. I think this is a trickier look to pull off, that's why in my current shape I would go for the long blazer.

These bells currently do not fit... And I'm only wearing a 1.25" heel which is barely high enough (the jeans are a petite inseam so no option to wear higher).

Here's another attempt with the flares. I wore these exactly these two times. Good thing I don't track CPW. I think the looser top is more flattering than the first attempt above.

I wear bootcut jean pretty much exclusively (one pair of jeggings/boyfriend jeans otherwise) and I find that I buy two different lengths - one for heels and ones for flats. I prefer bootcuts to skinnys, because I have hips and large breasts, and I feel that bootcuts balance my silhouette better - skinnys make me feel like a diamond shape, balancing on a point!

I do find that some bootcut styles have too much fabric at the bottom (but not enough to be flares), you should look for styles where the hem is about the same width as the waist or no more than a inch wider than the waistband when you're looking at them as one leg (like, fold the jeans in half so that you can only see one leg all the way down, then fold them so the hem touches the waistband). Also, the angle should not be too sharp, i.e. the extra fabric shouldn't be immediately obvious other than 'these aren't skinny/mum jeans/boyfriend' styles.

As a 5ft tall hourglass with a tummy shape, I wear them with tees/jumpers that skim over the waist (but only a couple of inches. Any longer than that, I tuck and 'blouse'), and I only tuck in the top fully if I'm wearing another layer that will skim over the waistline (like a jumper or hoodie).
I do tuck in camis, usually because I'm wearing them under a tee/top which hits on or just above the waist (but I don't like draughts, and prefer to be covered so that I don't get cold air blowing straight onto my skin), but vests/sleeveless tops in summer are worn loose.
Generally for tops, I tend to go with slimmer/tighter styles rather than floaty/wider at the hem styles, simply because they tend to fit as a block from under my breasts down to my hips and somewhat disguise the tummy bulge.

Re footwear, I subscribe to the rules that trousers should sit about an inch (or thereabouts) from the ground in heels. Flats are more difficult for me, since no matter the style of jeans the hems tend to drag on the ground a little, but thus the different lengths and I just trim them if they start to fray!
I also tend to go with black/dark footwear for dark wash jeans, and lighter or brown for light wash (I do the same with other trousers), simply because I feel that the other way round can draw too much attention to the foot area and therefore the extra fabric!
Hope this helps!

I love boot cut jeans and pants. I wish I could attach a picture to show you what I am wearing today. I have very retro boot cut black/white striped pants on with a sleeveless mock turtleneck sweater. I rarely wear anything tucked in. Depending on how long the pants are (I am 5ft2) I either wear a heel or a slip on bootie that cuts at the ankle. I would not wear a long shirt with a boot cut pant. Something that just cuts past the waist works for me. I also love a jacket with a boot cut. I have a few leather ones I wear and I bought a peach velvet blazer from White house black market that works very well with my boot cut jeans. It hits just below the waist.

These are the pants I am wearing..
https://www.macys.com/shop/pro.....ys?ID=5373

I like what Gryffin said about a substantial shoe. Wedges would be great, and those would also be comfortable. You could pair that with Boho, flowy tops. I wear my bootcuts with flats, too, I just fold them up.

Lisa, I was inspired by this thread to pull out my bootcuts (actually I think Angie would call these flares but whatever) tonight. Lighting is terrible but they are dark denim, very long with my burgundy pikolino booties (2” heel, almond toe), a faux wrap tunic thingy, and little black jacket.

I have to say that the 2nd photo CocoLion posted is for me the perfect current way of styling a pair of bootcuts. Slightly longer/looser top is key, in my view. Sure, they look great with fitted tops too but when I try this look now, I feel like I’m back in time, 15 years ago. It might be totally subjective but I don’t want to go there:).
Also, I’d like to add that I just love boot cut jeans. The trick for me is to style them in a way that doesn’t say “that’s what I’ve been wearing for the last 20 years”.

Diana - this is great ! Excellent proportions and you look fantastic .

Hi Lisa --

Since you say you want to maximize leg-lengthening and elongation I think you'll find bootcuts vs flares *are* they way to go.

I wear both and notice a difference. To give hard numbers vs subjective descriptions: my now-"vintage" bootcuts are 18" around and the relatively newer flares 21."

I have always been a fan of the bootcut ,to my eye they are the most elegant of jeans and make everyone s legs look longer.Just looking at all the photos people have posted on this thread proves that .I don’t think that there is a dud outfit amongst them so I really hope that you find a way to wear them that feels comfortable to you as I m sure that they will be very flattering .
Suz-I did a double take looking at your photos ,you could be Angie’s sister .

Ha! Thanks Cardiff Girl, that is a compliment. A shorter, less slim, and much older sister. Different face shape, eye colour, and (now) hair colour, too.

But we do share a general body type, quite a few body type modifiers, and a general style sensibility -- kind of like Angie and Sam.

I love my Paige bootcuts. I feel like they make me look taller. Not into bell bottoms or wide flares, as I'm too short to pull off that much fabric and width. I wear mine with boots, mainly, and with sandals in the summer.

I posted the first outfit the other day. The white pair have gone to eBay heaven as they were a little big - they were also Paige. My sister's cropped straights are a nice contrast, for example! I am looking to replace them this summer.

Your Paige bootcuts look great , Laurie . Thanks for posting this here .

This is a really useful and interesting post. My favorite outfit of all is Diana's most recent - that is absolutely on point. I think I need the entire thing - especially that faux wrap tunic piece.

Vivian - I agree. Diana - start shopping for us

Here's a bit of reverse engineering, for what it's worth: today I found a jacket in a thrift shop (Escada b&w striped tropical wool with dotted silk lining, beautifully made) that is longer and sleeker than the short jackets I tend to wear--almost mid-thigh. It occurred to me that it could function as a lightweight Spring coat with the right pants. The jacket has slightly extended, very defined shoulders, and when I tried it on, I thought: long boot-legged jeans, preferably white or very dark (neither of which I own at the moment). So, if any of your gorgeous, sharp-shouldered Smythe jackets are longer than most, you might start with them...

I liked the way Angie was wearing bootcuts in the 12 year blog post today - I know it is an old picture but it does not look dated to me. I imagine you have similar components in your wardrobe.

I agree with Sally. That photo of Angie does not look dated at all! And I think that would work well with your jackets.

The other look for boot cuts or flares that I like is what I call the Rachel Zoe look. Long tunic with shorter jacket. I had some fun emulating it in this post.

https://youlookfab.com/welookf.....rachel-zoe