Hiya
I hope you don't mind my input. I am more of a girly city girl than down to earth, I usually have to get dressed up like I am going out for my job (work evenings in a small restaurant), but still faced some challenges when I was more chubby than now. I found that I had to dress differently for my body type - the styles and cuts that I wore when skinny no longer suited me when chubby. And wearing the correct colours is essential to looking good, especially while aging. I spent ages looking for the perfect pair of pants and, once I found them, wore them to death (I have even altered them so I can continue wearing them even though I am about 35lbs lighter)...looser thighs, hang straight from the hips, in fine knit polyester...go with everything. Actually, I wound up with a lot of polyester knit clothes, as the fabric drapes well. A good foundation garment - a reinforced camisole with an underwire bra built in - really helped to make my shirts look good. Knickers that came down mid thigh for when I wore tight skirts helped smooth my bottom out. And yes, I am a huge fan of Trinny and Susannah's book - What You Wear Can Change Your Life - good foundation garments rule! I found a lot of tops that criss crossed or wrapped across my middle were good, created a waist and hid my belly. Straight, to the knee, fitted skirts are good as they show of shape and go well with a looser top. Tops fitted under the bust with a slight flare to them. Mid length sleeves, or short sleeves with some soft ruffles or gathers across the top so they don't hug right onto the upper arm and disguise a bit of the hello-good-bye-wobble. Nothing baggy, nothing too loose. Oh, and a larger cut belt more so than anything skinny. Skinny belts just looked as if I was trying to cut a sausage in half **grins**
One other thing I did was go have my make up assessed by a friend who does make up for a living. She only charged me $20, looked at all the make up that I owned, I showed her how I wear it, she made a few alternate suggestions, suggested a couple of new pieces to get, and I was on my way. The 20CAD was so well worth spending to get my stuff sorted out.
And one final thing I do is to peruse the Internet for fashion advice. There are loads of sites out there done up by folks who just enjoy clothes. Not the high fashion sites, but blogs...some folks just enjoy clothing, talking about it, playing with it, and take pics of their clothes and talk about their latest acquisitions. I find it is a fun way to see what other folks are doing.
That's about it! I hope you have fun on your clothing venture! Good luck, and enjoy the journey! I better get offline, and go stick some clothes on for working tonight...
One final thing... Unless I feel beautiful in something, I don't keep it. I used that adage when clearing out my closet a few years ago, and I still stick with it. Everything I wear...I have to feel beautiful. If I don't, then out it goes. I find that if I don't feel beautiful in it, then what is the point of wearing it when my goal is to feel and look as attractive as possible. Only wear the things you love. And if you love it heaps, buy two!
Lou