I've been dieting and exercising, and I've lost at least 20 lbs so far. I still have a long way to go. I don't want to invest in new clothes every time I drop a size. How do I stretch out the wear of the clothes even when they're obviously baggy?

I know they aren't as trendy as they once were, but I find simple jersey skirts work great during weight changes. Paired with a more elegant top like a sweater-pullover, they aren't going to look baggy or frumpy. You can get them affordably at American Apparel, but I don't really know if I want to endorse the company given what I've heard about sexism within the company (see article link below)…

http://www.infoshop.org/inews/article.php?...050804154742932

I think that matte jersey, maybe not skirts, but wrap tops and dresses would be a great way to look slender, kimono dresses would also work. kimono tops. anything babydoll-ish and in some sort of knit stretchy fabric. old navy has some really fab jersey dresses and I dunno about tops… I know it sounds weird, but maybe check out some maternity style dresses, because they are meant to stretch with the wearer. this adorable dress is affordable and looks sort of high end

http://www.oldnavy.com/browse/product.do?c...;scid=417880002

this top seems sort of dressy and will work for a svelter you and a current you

http://www.oldnavy.com/browse/product.do?c...;scid=505644002

trapeze tops and dresses are versatile, and I think you can wear the same tops and just have an adjustable belt. woven belts with no holes will work for your current size. while this belt seems a little expensive, because its braided, it can keep on cinching for losing even a couple inches.

http://www.oldnavy.com/browse/product.do?c...;scid=505499022

http://www.oldnavy.com/browse/product.do?c...;scid=540921002

and knit empire waist dresses in smaller sizes can work for your currently larger belly, and look oh so chic in a drapy way a couple sizes smaller

http://www.oldnavy.com/browse/product.do?c...;scid=492965032

http://www.oldnavy.com/browse/product.do?c...;scid=480177132

http://www.oldnavy.com/browse/product.do?c...;scid=508662052

try wearing bright colored hose with neutral dresses in fall to cover your legs for extra warmth.

knee socks can be worn with a pair of grown up (no pastel colors unless you are like 15) warm colored pumps and a dress for a trendy look.

http://www.oldnavy.com/browse/product.do?c...;scid=505465012

wearing a pair of black cotton tights in a skinny jean style (not a sock knit, but not a hose knit) kind of like the tights you find in the girls section in walmart, underneath a dress or kimono top can look like skinnies, and pair of knee socks and pumps can be very cool and trendy looking. those cotton skinny sweatpants are inexpensive and usually below 10, so you can get a couple to replace the wearing of trousers or jeans, if you like. the waistbands are extensible, so they can go in.

all of the things I provided links for are all told, 88.98… just in case you wanted to know

I suppose I should have mentioned that I tend toward the preppy/androgynous look.

And I'm still plus-sized, so Old Navy can go suck eggs.

If you have a polo dress, maybe try to cinch it with a skinny belt for a more figure flattering look… also, should the kimono/babydoll styles have enough space for larger tummy and chest??? especially the kimono dress in a larger size should be pretty roomy for a larger chest and tummy. try them on first, before passing judgement on the trapeze/babydoll dresses. in any case, good luck on losing weight!

maybe you should try a quick inside stitch on the inside of your clothes… thats what I do when people buy me oversized clothes.

A wrap dress can be worn tighter or looser. Target has some good ones for about $25 on their website.

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Pants would probably be the hardest thing to hide the fit on. You can wear a belt but at a certain point even that's not going to help much. The baggy areas in the legs and butt become obvious, too, and can make you look like you're bigger than you are.

I have the opposite problem in that I've gained 20 pounds and am trying not to buy new clothes (for money reasons and to try and make myself lose the weight). I'm a big fan of Targets cotton skirts, empire waisted tops, and the peasant style blouses.

Maybe if you sew in elastic into the pants it might help. personally never tried it. If its baggy in the thigh and butt, you can always cut it at the knee and it can look more like gauchos/walking shorts. wearing tunics can camoflauge a baggy butt of a jean…