Understated, yet chic, over-the-knee boots have endured the test of time, but most significantly, look and feel best when paired with a very classic look. (Your style reference should be someone like Jackie Onassis, jaunting through the Hamptons, rather than Julia Roberts in Pretty Woman, strolling down Hollywood Boulevard.) Boots Stick to neutral colors, like black, camel, and brown, to achieve that authentic equestrian vibe and look for practical heel heights. Trust us, you'll appreciate a flat or lower heel when running around the city all day. Jeans The focus should be on the boots themselves, so the key is to avoid any of-the-moment trends. Timeless blue jeans in a clean dark or medium wash will keep your look feeling polished and professional. Top It Off It's still chilly out, so when it comes to the top half of your look, go for a rich camel sweater in cashmere or wool, and throw on a boyish blazer for that all-American feel. Subtle prints and contrast stitching add intrigue to the overall ensemble. Whether you're headed to the office or a casual weekend outing, we can assure you this outfit combination will work every time. Now giddy-up!