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The following are clothes that almost never go out of style. If you're out and about shopping, whether it be at a name brand store or mall, yard sales, thrift stores, or at a relative's house and they're getting rid of some of their clothes look for these.
plain pull over sweaters. t shirt material long or short sleeve shirt even a henly with a collar. i think anything in a solid color would be safer to use than a print.
Shirts and shirt dresses. Simple sheaths. Sun dresses. Good jackets. Denim - skirts, jeans, shirts, jackets..Ballet flats ,loafers, Roman sandals, plain sneakers, boat shoes. Fitted t-shirts with long and short sleeves. Shells, knitted and fabric. Well- fitted trousers. Leggings. Caftans. and all sorts of ethnic clothing.
Things go in and out of style. The clue is to find out what suits you - (I have always loved shirt dresses) and then tweak your outfit to nod to fashion. Scarves and accessories like jewelry and belts and shoes and bags help.
Look at Donna Karan new collection - really chic plain costs mucho. So you are going to have to put your little touches on things to keep from looking too dowdy...
My choice is denim. It's been in style just about all my life and that's a long time. It's also comfortable and has no Static Cling. Ballet style shoes have also been a staple with me. Stylish and comfortable. Can't beat that.
A tan or black trench coat with belt, basic jeans, white tennis shoes, basic white blouse or shirt, black suit, jacket, pants, A line skirt. Princess style dresses, dark winter long coats, shawls, the basic litttle black dress, basic colored shoes, white, black, tan or cream, tan or navy skirts or pants, vintage beaded sweaters, any type broach, pin, watches, shawls and pearls!