A white and black vertical striped dress shirt and grey chinos? Make no mistake, this look will turn every head in the room. You know how to breathe an extra dose of style into this look: dark brown leather loafers. You're sure to always look good even despite the summer heat if you keep this outfit as a last-minute grab. When it comes to dressing ideas for gents in their 50s, this combination looks good on almost any man.