Yep, sounds like you're getting the idea. Specifically, with flares, I try to style them in a way that takes advantage of the potential casual rocker vibe (a leather moto, a dramatic sweater, etc.). For a grungier/preppier treatment, perhaps that would mean a tipped tailored blazer or a plaid shirt dressed up with pearls -- just examples, but you get the idea. Whatever makes YOU feel fab.

Krish, I've been following this thread since yesterday, so sorry I am just now commenting.
I think I know what you're saying...I tend to like most of the flattering silhouettes on myself, at least the ones that don't include heels, because they are not exactly heaven on my feet. It was interesting to read Suz' take on this. I'd like to sit in on your fashion discussion as a fellow long body/short legs type! Seeing the pictures that other people took of me over the weekend, the only thing I can think is, "MY, what a long body I have!" It is sending me back to the drawing board, and I thought I was doing a lot of things right.

bj1111, thank you, those pics are so inspiring! I really like the one from Classy Ever After, I even own a very similar Dansko pair of clogs, and the funky necklace brings it all together.

Sam, you have a good point there. Hadn't thought about it. Better feel and look comfortable in a less flattering outfit that wearing something safe in which you are and look painfully bored/uneasy/unhappy.

Janet, again, excellent ideas! I love the plaid shirt-boot leg combo!

Claire, you have such a GREAT silhouette! I don't find it to be particularly "long", but certainly svelte and elegant. But I understand how our own eye always catches something nobody else seems to notice.

I totally understand. The other day I picked out a neon graphic button down and white linen pants buttoned to the top. But I had lost some weight, and the pants looked large to me (boyfriend style), so I didn't wear them. At the last minute I changed into very flattering (but not right for the top) jeans and the whole outfit fell flat. I got 2 compliments on the top, but that was it. Dressing for safety is a mixed risk. I was more concerned about saggy bum than the styling of the outfit. With my limited wardrobe capsule, those are the risks I take.

Bostonsmama, what a great story, and incidents like this are precisely what I mean. Sometimes, all it takes is one thing to be off for the whole plan to fall. In your case it's the weight change. And you are right: sometimes last minute changes like this one offers a new combination that is a fresh take on something we love; yet sometimes it just.... doesn't work. Yet one would have thought that the very good jean fit would have arranged it all... and it didn't.

BTW laugh at me all you want, me too am struggling with butt-weight loss, which is an unwanted loss because it greatly affects the fit of a lot of my jeans and pants, and even some skirts. Mind you I am not what you would call stick thin, and I do work out. So... I have started using (I know, I know) a bootie booster girdle. I had bought it about two years ago in a moment of brain absence while shopping for tights, and the SA praised it as the latest genius invention: a panty with two inside pockets containing pads, just like those of a push up bra (only a push up panty, so larger). I had tried it a couple of times at home but misplaced the pads too high and thought it looked ridiculous - which it indeed, with this placement, did. I felt really bad for the $ spent on it and hid it far away at the bottom of my drawer. Lately, I decided to give it a second try, because why not, and played around with the pads. I tried placing them where a butt would protrude, and put on some skinny jeans... to my dismay, instead of making me look fat or slapping an awkward sudden kardashian simulacrum under my face like I had thought, it gave me a sexy, tight-looking behind, slimming my legs and tummy in comparison. So I rediscovered this tool. I don't use it all the time, but it is useful for tighter fitting clothes and I thought I'd share it with you.

This thread is so interesting. I'm trying to learn and glean ideas here! I was just thinking today that I really like the return of boxy tops. I used to love them, and I thought they were a good shape for me, because I didn't think I had a waist. But then in the years of high figure flattery, I discovered I did have a waist--just not a super-defined one. So for several years I was trying so hard to avoid boxy tops (successfully, I guess, because I now don't seem to be able to re-create the looks I admire involving looser, shorter tops). I was trying to follow the guideline of showing my waist--belting long cardigans and straight dresses, wearing my cardigans buttoned in the middle over body-conscious layering tops. I think most days I pretty much live in the land of Just Flattering Enough. I like my flat shoes for a lot of days, I like the feel of boyfriend jeans even though I think they do next to nothing for my rear end, flattery-wise, and I rarely try to show my actual waist. I'm not sure I even know what is most conventionally flattering on me, frankly, besides revealing a waistline.

Firecracker, remember that each time something comes back in style, the cut is never quite the same. Therefore it might be hard to recreate a feel or a look we once wore. I also struggle with this time's boxy tops, and I suspect it is merely a question of hem: in the eighties, the hem was higher (because the jeans' waist was higher). Today's boxy often means a square from shoulders to hips, which is difficult to pull if you have the least bit of hips or top heavy tendencies. Just an hypothesis.
An option for you instead of the all-around boxy top might be high low boxy, where the front is cut higher?

Wow, what a good insight on the difference! I do love to wear the high-low tops. And I'm all over the semi-tuck, which has a similar look--as I said on a recent discussion about it, I really don't know how I used to dress without it! So maybe those are my "boxy" top looks now. I can handle that.