If the setting permits laid-back styling, consider teaming a white and red crew-neck t-shirt with jeans. You could perhaps get a little creative on the shoe front and dress up your look with black leather brogue boots. A good illustration of functional fashion, this ensemble must be in your closet when winter weather settles in. So if you need outfit ideas on how to dress as you head into your 50s, this ensemble is definitely worth saving for later.