Even with the increased availability of trendy styles for mature women, classic styles should remain a wardrobe staple, says FashionAfter50.com. Retro trends can actually make your wardrobe appear dated, the website warns, as if you saved the clothing until it came back in style. Shops such as Ann Taylor and Talbots cater to women seeking stylish career clothing with classic lines, as well as sport and resort wear, in petite and regular sizes.