It looks like lace clothing is going to be popular this fall and winter along with plaids. Look for lace that is soft to the touch, not stiff and scratchy against the skin. Make sure that the plaid patterns are matched at every seam of a garment. Lace and plaid look very good together as long as the lace is white, cream or black.
Plus size clothing is not always stylish. The large patterns and thin fabrics are not becoming to women with curves. My advice is to find a brand or "label" that has coordinating pieces in black or navy blue. Buy a shell type top, the jacket that goes with it and a pair of slacks (not capris) and/or skirt. When you have these items in your closet you can add accessories to dress them up or down. Add animal prints for casual events and add things that sparkle and shine for more formal events. If you buy black or navy shoes to go with your three pieces that's even better. Be sure to have the shoes with you if you have to have the slacks or skirt hemmed.
When you clean out your closet use white or clear garbage bags, not black ones, to hold things you plan to give away or donate. You can see through the clear and white bags and you're not as likely to throw the bags in the trash. You can also buy bags that have red ties and only use them for things you plan to donate. Use old gift wrap ribbon tied to the garbage bag for long term storage. When you see the ribbon you will remember to go through the contents of the bag before throwing it in the trash.
I've noticed recently that women of all ages are responding to conversations regarding "pretty," as in dressing up to look pretty. Maybe women are just programmed to respond when we hear the word but I've seen women stop talking to someone and turn their attention to the person who is talking about being pretty. I think women are tired of the same old "look" of blue jeans and sloppy tops. I think that look as been done every way possible and we are ready to move on to something more feminine. It's difficult to go from jeans to formal wear because they are at opposite ends of the style spectrum. If you are not used to wearing anything but jeans and shorts then you may not be comfortable wearing formal dresses at events. A woman's posture has to be different when dressing up. A woman needs to walk differently, sit differently, get in and out of vehicles differently. She needs to know about good foundation garments like well fitting bras and Spanx or other control panties. I can always spot the women in a bridal party who are not used to dressing up. Their stride is too long from always wearing pants, they teeter on their heels because they are used to wearing flip flops and flats. Their bra straps reveal their very old, ill fitting bras. They usually have a mid-section issue because they don't own a foundation garment that slims the waist. Their posture is slumped over because they are always texting. The old fashioned "walking with a book on the head" from the days of charm schools still works to straighten the back and shorten the step. This will help you feel more feminine when you dress up!