Ty Webb
Bushwood Country Club Shirt and Golf Cap from Caddyshack

"A flute without holes, is not a flute. A donut without a hole, is a Danish..."
Ty's look is preppy but casual and easily recreated with some simple clothing staples that can be easily sourced from a friend's closet or local thrift store.
Start with a white golf cap. We got ours at a vintage shop.
Pair with an beige button up and white slacks.
Round out the look with a white golf glove for the left hand (about $5-$10) and cleated shoes. We fished ours out of the bins at our local Goodwill and they were cheap, about $5.
Don't forget a purplish eye wrap for effect. Chicks dig trick shots.
Then the final touch: a golf bag and clubs to bring the ensemble together. The local thrift shop is a great source of cheap golf clubs and bags; this collection cost set us back about $20.
For a group twist, recruit a friend to costume as Danny Noonan or Tony D'Annunzio. You'll have more fun and they'll save you the trouble of lugging clubs from party to party!
