I love hats with ear flaps for boys--they are so outdoorsy and sweet--and my favorite for fall/winter is the wool Issac ($30, 12 months - 6 years) from Short Hats. Based in Colorado, Short Hats designs some of the cutest headwear for children, including heirloom-quality hand-knit beanies , the trendy Riley cap, and classic hats that will never go out of style like the Gatsbyesque Buster. I also love that Short Hats uses recycled plastic visors in their brimmed hats, their knit hats are handmade in Argentina by companies that treat their workers fairly, and the rest of the hats in the collection are made in the U.S.
Just for Unboring Boys readers: Short Hats is offering a 10 percent discount on items in their online shop through 1/1/2010! Enter coupon code "Unboring" at checkout. Factor in free shipping (on all U.S. orders) and that's a sweet deal! Visit http:www.shorthats.com/kids-hats-summer-and-winter.php to check out all the fabulous styles.