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.
This is the classic silhouette for a reasonable price.
$90 at Topshop.
Wanna add a little tough-girl edge to your boots? No better way than with a metal heel.
$99.90 at Zara.
Like the classic look but want a little height? Try these on for size.
$92.82 at ASOS.
We're digging the sporty bent to these—a surprisingly on-trend pick for all-weather wear.
$99.99 at Zappos.
Another edgy pick, these have the attitude focused on the toe, reinforced with a bit of metal.
$80.36 at Nordstrom.
Who says all Chelsea boots need to be uber sleek? We love the strap detailing on this pair.
$79.95 at Nordstrom.
The Hippie Pick
Alright, these are a bit costume-y, but we like them nonetheless. Great if you want to think a bit outside the box.
$84 at Topshop.
We like how these kind of resemble hiking boots, what with the treads. (Though we wouldn't want to even attempt hiking with those killer heels.)
$98 at Nasty Gal.
Chelsea boots are mod in and of themselves, but take it one step further with this cool colorblocked pair.
$75.94 at ASOS.
Most Chelsea boots are either flat or have a very visible heel, so these hidden wedges are a bit unexpected.
$36.80 at Forever21.