To look like a proper dandy, pair a charcoal blazer with white dress pants. When in doubt about what to wear in the footwear department, stick to a pair of loafers. During the winter season, when practicality is top priority, it can be easy to settle for a less-than-stylish outfit in the name of practicality. This outfit, however, is a clear example that you can actually stay cozy and remain stylish in the winter season. This pairing proves that even after sixty you still have a vast array of dressing options.