1. Button-Down Skirt

This high-waisted red skirt ($34.50, alloy.com) isn't as sleek as Kerry's, but we think it's equally cute! We love the white-trimmed pockets on the front.

2. Red-Trimmed Tank

If you're gonna do the shirt tuck, you gotta get a cute tank like this one ($26.50, alloy.com). The adorable red trim will match your skirt, and the silver buttons add some sass.

3. Cinch Belt

If you're going to cinch your waist, then wear a belt that's easy to wrap-around. Kerry's skinny belt is nice, but it's a little too plain and formal for our taste. That's why we suggest buckling this one ($14.50, alloy.com) up.

4. Plaid Wristlet

With kiss-lock closure and a handy, removable wristlet, this purse is clutch! Black-and-white patterns are hot as heck, so you'd be wise to get this versatile-and-cute accessory.

5. Canvas Slingbacks

What better way to show off your legs than with a short skirt and high heels?! These pretty platforms ($32.50, alloy.com) will add height and class to your already cute ensemble. Fun!