Frye Carmen Harness Short, $298 at thefryecompany.com: Here are the booties. They also come in a taupey-grey.
Okay, so the way I see it you can go three ways: one, the casual-cute way with boots and a top, two, the Taylor Swift sundress way, and three, the boho way.
Alice + Olivia Dress with Organza Skirt, $298 at shopbop.com, Of Two Minds Stevie Dress, $345 at shopbop.com: So here's the TSwift route. It's very predictable, but it is also really fun and easy to wear. The boots anchor the floaty white dress nicely, and it's a complete outfit in literally two pieces. Think about how easy that is in the morning when you've put your alarm on snooze five times and don't even have time to wash your face before running off to class. The boho option is also a very simple outfit. The hippie dippie trippy dress and cowboy boots combo is very '70s, and very on-trend at the moment. It's very much an It Girl outfit, something easy that you just throw on, but somehow you end up looking like a million bucks and crazy cool.
J. Bran Straight Leg Medium Rise Jeans, $159 at shopbop.com, Helianthus Top, $88 at anthropologie.com: I really want to keep the focus on the boots here, so I'd go for a dark wash, straight leg pair of jeans. I know I've posted these J. Brand jeans like 10 times, but I really love them. They fit me perfectly, they fit my mom perfectly, and they fit my roommate perfectly, and we all have TOTALLY different body types (as in athletic, waifish, and hourglass). I think that with such rugged boots and basic jeans, it's nice to add in a little girliness with a soft, feminine top like this. It's very sweet and subtle, so it doesn't take away from the boots, but the texture gives it just enough detail to keep the overall outfit interesting. Plus, that blush/off-white hue is universally flattering, as are the v-neck and fitted waist.
Images from thefryecompany.com, shopbop.com, shopbop.com, shopbop.com, anthropologie.com.