Please forgive the long post, as it isn't too much of a reply to your comment, but more of me rambling on about how much better my clothes fit now that I know what to look for! Smiley
BadChemist, please please please come shopping with me!
I know all these tricks exist. I KNOW that the right clothes can take pounds off of me and add inches to my height. I TRY to dress like a grownup but being short waisted, short legged, and not exactly svelte makes it hard.
I have always BEGGED my friends to put me on What Not to Wear because even though it's an unrealistic budget, I really need someone to take me in hand and show me the tricks. I'd look at it like a college course or something. I'd value the tips more than the budget. I loathe shopping for clothes because I'm so bad at it.
I've decided at 43 that my only hope is to make enough money to be able to afford to hire someone to dress me, as I'm clearly never going to learn to do it myself.
My best friend would be HORRIFIED to hear anyone ask me for shopping tips!

She's been a good teacher, though. Let's see... where do you want to start? I'll throw out some stuff out there, but I hope everyone here pitches in, as I'm still learning!
The most generic and important tip I can give you is that if you have ANY doubts about how something looks on you, DON'T BUY IT. I would have saved a lot of money if I had been better at that. You may think "Oh, it's so cute!!" but if it's not cute on you, it's never worth the money, no matter how cheap. Trust me, I've been there. Don't buy anything that's too long or too short, thinking it'll be ok regardless.
The second most important tip is to try something that you'll never think will look good on you. For me, pink shirts, red-orange tanktops, and a jacket that's tighter than I'd like worked out beautifully. Don't be afraid of fitted clothing. Baggy clothes just make the lumps look bigger because they'll drape over them. You just have to look for the snugness to be in the right places. I don't like t-shirts that have spandex in them, because they'll hug my belly. I do, however, like an empire-waist with a v-neck, which gives the illusion that I actually have boobs. Look, Ma! No surgery!
Watch for colors to flatter you. Work with your height. As for being short-legged, I have the same issue, but I hold out for the perfect length pants, even if they're a little pricier. I generally don't like spending a lot on clothes, but I will splurge on a great jacket or perfect-fitting jeans. I've been ordering a ton of jeans from the Gap, because their petite line is only online. I buy enough pairs to get free shipping, then return the ones I don't like or that don't fit.
Don't resort to cuffing too-long pants! That's the biggest sin against creating a clean line. I was doing it for years when my best friend pointed out that it actually made me look SHORTER and my legs stubbier. I was aghast to see that she's right. So, I either hold out until I find the right pair, tailor too-long pairs, or buy longer pants and wear them with the right shoes. My favorite jeans are from American Eagle, but their shortest length is still an inch too long. So, I wear them with flipflips or heels.
Jewelry really dresses up an outfit. I'm obsessed with good necklaces now. Good necklaces do not have to be expensive... the costume stuff will look just as good. A great necklace, however, can dress up a basic top with jeans. So, whenever I'm out and about, I keep an eye out for cool pieces.
Oh, and whatever you do, buy clothing that will go well with more than one other article in your closet! For my OP, that was one of the cons of the jacket my mother gave me... purple didn't work well with my wardrobe and I didn't have anything that matched the colors in the plaid pattern.