For whatever reason, most equestrians around here are female. If we lived in the south where cowboys are an actual thing, or in England where scores of men fox hunt and play polo, then things would be different. But we live in Wisconsin. Male riders aren't super common in these parts, but there's usually that One Guy Who Rides at every barn, and he deserves a Christmas gift just for putting up with all us crazy horse ladies.
1. Heritage leather trail riding gloves. Equal parts work glove and riding glove, long-wearing and practical.
2. Bluetooth speaker for his saddle, because he has broken two cell-phone already by dropping them while riding.
3. Helmet/headlamp for doing chores in the dark or night-time trail rides.
4. Custom leather saddle bags, to pack a trail lunch in.