It's true that every body looks good in different things. Like runningfromfat (and you are considered hour glass as hips are usually a tad wider than bust for hourglass shapes), if you are chesty and have hips, having things be loose like that makes you look big all over. So, if you have a shape in teh middle, it's way more slenderizing to have form fitting.
Now people who have long middles (those who are tall with long torsos) can looks so great in long, flowing, baggy clothes. And so on. My guess is usually what you prefer for clothes is usually the best look for you.
I do like the Eileen Fisher stuff a lot. (I adore linen!)
A lot of the stuff I like is big but body skimming -- soft drapey fabrics that are not stiff and tent-like. I just found this and I really like it, though I'd make it without the sleeves, probably a size or two bigger than my measurements, lol, and wear it over a tight cami, not buttoned all the way up, in a different fabric: voguepatterns.mccall.com/v1177-products-11085.php?page_id=857 If I didn't sew I'd be in big trouble as it is hard to find stuff that really suits my style. But this top would not be maternity-ish or tent like and I think it could be very flattering on a slim body. I don't think I'd want to attempt it until I was pretty close to goal weight as I could see it looking a little frumpy with big butt and a belly.
I said I was a pear, which is how I think of myself, I guess. I always forget I've got these giant boobs. I am hoping that they go back down to a more normal feeling C or so. But Between 214 and 180, they haven't changed a bit. I'm still a DD, so I'm not sure how that's gonna go. Last time I was this weight I was a D and when I was near my goal 15 years ago I think I was like a barely C or so.
i LOVE wearing baggy clothes...my favorites are a pair of sweatpants and a sweatshirt that i've had for awhile now...interestingly enough, when i was younger, i preferred leggings and looser, longer shirts...then i liked to wear tight jeans for several years...when i became pregnant with my second baby, i began to dislike tight clothing and refused to wear it during pregnancy...i enjoyed loose-fitting yoga pants and loose shirts...but the feeling never went away after my baby was born...i still HATE to wear tight pants and tight shirts, jeans have such thick material and are restrictive to movement, in my way of thinking and i get nearly claustrophobic in tight leggings or tight shirts, especially if it has a tight neckline....heck i dont even like tight necklaces like chokers....im trying now to wear tighter shirts since i've lost a little weight, but i still dont like it...and i still wear yoga pants as much as i can...luckily i have a job where i dont have to be super-dressy
I end up with baggy things because it's better than too tight. Clothes simply aren't made the shape I am, so I buy them to fit the bigger parts, and they'll be loose on the smaller parts. My waist is comparatively small, but I transition too quickly. If something fit me in the waist, it would be too tight in the boobs and hips. And clothes that are shaped don't expect to hit my hips so soon. (I always end up personifying clothing.) So I don't think it's ideal, but baggy ends up as a way of life for me.
I've got a big bust and hips, so baggy clothes have NEVER looked good on me, even when I wasn't too heavy. Which is sad, because I really adore some of the flowy "hippie" type clothes and dresses. But I'll never get away with wearing them without looking like I'm wearing a two person tent. I don't like tight clothes tho, I prefer tailored and comfortable to form fitting, I refuse to stuff myself into leggings.