50s: You don't have patience for things that don't work, and that also extends to your basics. Durable, extra-cozy, and super-versatile, the pieces you're looking for aren't that different than what you've been wearing for most of your life, but they do treat you with a little extra TLC. Some extra stretch in your denim and volume in your sweater will make you look modern, not juvenile.

T-shirt — The Row is like the Rolls Royce of shirts. Sure, you may need to wear a slip underneath, but the super-fine cotton will feel like a dream next to your skin. You deserve it!
The Row Sabeene Top, $135.95, available at Browns.

Jeans — A.P.C.'s raw denim may take a bit to break in, but, like you already know, everything worth enjoying takes a little work.
A.P.C. Shorter New Cure Denim, $280, available at A.P.C..  

Cashmere Sweater — The so, so soft sensation of your favorite sweater material is just as dreamy, especially now that you opt for Vince's looser-cut shape that effortlessly flows and pairs great with any item from your stand-out accessories collection.
Vince Wool Sweater, $364.37, available at My Wardrobe.