First up: Socks!
No, stick with me here. Having really nice socks is a big deal for your target audience.
But each will prioritise different sorts of socks. You need to Know Your Middle Aged Man
Comfort: Bridgedale wool socks with padded soles.
Quirky: This can be big for men for whom novelty ties are a step too far. Try Art Socks https://shop.nationalgallery.ie/collections/art-socks
Luxury: Bright colours, very if you know you know, sock makers to the pope. https://meschaussettesrouges.com/en/collections/chaussettes-gammarelli