I certainly remember You, too-then and now a beautiful lady!:-) and I can relate (loosing myself from time to time due ilneess or weight fluctuation) but shall I say a style refresh/renewal will help to gain your confidence back. Try to see and emphasize your benefits (beautiful face, complexion and hair, feminine hourglass figure, etc.) rather than sticking with older dressing ruts which don't work for you anymore. Focus on one outfit at a time-take notes what you love or not wearing and start from there-one step at a time. It will quickly brig back your mojo, you know you are fab inside and out!
I see dresses love you- bet even a shorter shift/sheat will look fab on you+ layering can be fab on You! What about finding some skirts as well (tube with a BF blazer, pleated midis with fitted tees and denim jackets for more structure, denim skirts to knees with some hooded cardis, etc). I would all style them with on trend casual shoes, like sneakers& chunky loafers) and NOT HEELS-so dressing them all down a bit. Some girls here are trendy on bottoms and feet-, others can be more classic on top(&torso)-but trendy on feet. why not!