The Chelsea boot silhouette is one of our favorite fall shoe silhouettes—the classic look is always cool, adding some hipness to pretty much any look. They're versatile, too. Finish off a casual look (oversized button-down plaid shirt, jeans) or something a bit fancier (cool long-sleeved dress and tights) with the same aplomb. Chelsea boots add something a bit retro to any outfit—channel The Beatles any time you put them on—but it's a style that's endured. You can expect to really shell out for nice boots, but we managed to round up a good selection of Chelseas for just under $100. Click through and nab your favorite pair.