Opt for a red crew-neck sweater and jeans if you wish to look cool and casual without too much effort. Let your styling savvy truly shine by rounding off this look with black canvas low top sneakers. Putting together a well-coordinated combo can be a bit of a challenge on its own. Add below-freezing temperatures into the equation, and the whole thing becomes all the more difficult. Luckily, this here is your winter inspo. So if you need fashion inspiration for dressing as you step into your 50s, this ensemble is perfect.