LOL at kkards — yes, I have done that too, and said to myself WHY did I cut the darn tags?? Ugh.

Thank you all for the styling suggestions, and of course, you are all bang-on. I had earlier success with wide legs (cropped though) , and all of it involved semi tucking and a more refined shoe. But sometimes you just want to throw your clothes on and go without having to overthink everything - you know? Clearly, that strategy doesn't work for me , lol.

kkards - YES, I have done that so many times, which is the one big reason I gave myself permission to test these in the wild. It's not like I went to the gym in them or ate lunch in them, did anything different than would have happened inside my own house.

Roxanne - you get it, thanks. I am still leery /leary (no spellcheck here, ha) of wearing cropped and tucked tops/jackets. I think unless I drop 20 more lbs, I will always be self-conscious of slim fitting things on top. I have a bad habit of buying my sweaters and t-shirts too big because of it, and this sweater is a perfect example. All of this fussing to make a look work takes the fun out of it, and unless it just happens organically, I'm out. I don't WANT to wear dressier, heeled boots with wide jeans to go shopping - you know?

Lisa - I totally hear you. For the record, I was not suggesting that you wear your wide legs with higher heeled booties and a fitted top. It works for me because I have a more traditional style and a more conventional eye for proportions on myself, not to mention a dressier work environment.

Your style is more current and fashion forward than mine, so I actually think that sneakers and a fluid top look great on you with flares - and fit your lifestyle better. It's a matter of finding the right one, and whether it's worth it to you to add a new silhouette in your wardrobe. But I do agree - I think crops are easier to style because that tiny bit of ankle makes all the difference.

That's a great idea, texstyle. I'm loving my straight legs and they feel fresh to me. Some are hemmed to the ankle and some are raw edge. They look great over a bootie but equally good with a sneaker.

For me I have a rule, I can only bear one (maximum maximorum 2!) items with casual features at one time in an outfit- or I would feel overly sloppy even for my casuals. I deliberatley didn't say 1 or 2 "casual item" at a time, because categorization of dressy vs. casual clothing item doesn't seem to work anymore. You have 4 here (sneaks, denim and the kind of bag& sweater I think...). Perhaps this may be a good place to start with and pobserve your own limits.

Vice versa is even more strict for me, I can only wear only 1 casual featured item in a dressy outfit and still feeling dressy enough (for ex a denim jacket- or a cardi-over a party dress-for on the way).

lyn67 - that is SO smart, and you are dead right here. See, I never think of these things when getting dressed - I just put it all on and hope for the best.

and Marilyn, texstyle - great idea re straight leg jeans for this kind of look.

You don't look like the side of a barn, in this outfit or any other! But I understand about not feeling fab in the combo. I also think having a structured/edgy element, maybe a blazer or sleeker (could be flat) shoes would help. Or bootcut instead of all over wide leg jeans.

On the road so haven't read all comments but it sounds as if you felt the way I did wearing my Cons and the BF jeans -- just too sloppy. I get it. A bootie might have helped but if you don't like the jeans, let them go and experiment with the cropped version some more.

I know exactly what you mean Lisa. I see a lot of wide legs on other people and they look great . When I wear them I feel sloppy and in my eyes resemble a fire hydrant. I've tried so many iterations and cannot come up with what I like. I have two pairs of wide leg crops that I struggle with, I put them on to wear and end up getting changed EVERY TIME
I've also tried a straight leg and don't like that either. Guess I'll stay with skinnies for now as they make me happy but not particularly fashion forward.

Suz, Gail, thank you for this. Glad I'm not the only one.

"All of this fussing to make a look work takes the fun out of it, and unless it just happens organically, I'm out."

This is so wise. Adding this to my style mantras!!

I think your outfit looks good, but I have these jeans and am finding them difficult to wear also.