Irish Tweed Cap. Every guy needs an Irish cap or driving hat in his wardrobe. Forget the Kangol crap, and get a handmade wool cap in brown or grey. If you're a little saucy, go for tweed herringbone with a thin line of red running through it. While we're on the subject, wearing a ball cap turned backwards is never, ever okay unless you're in a baseball uniform and playing catcher.