Let’s Up The Risk Factor

J.W.Anderson Cotton-piqué Shirt Dress
Super Sunglasses Basic Sunglasses
Proenza Schouler Small Lunch Bag Clutch Calf Hair/Leather
Alexander Wang Antonia Leather Sandals
Essie 'For The Twill Of It'

I’m a big fan of keeping it casual, keeping it comfortable, and wearing jean cutoffs for any and all occasions, but there comes a time when you have to class it up and dress like a lady. And when it comes to embracing my femininity, there's no better style icon than Tom Cruise in Risky Business, obviously. No, seriously, dude looked great dancing in his tighty-whities—recreating that iconic scene shouldn’t just be limited to Halloween and theme parties. (Leandra pulled off a pretty excellent ode this week.) So, taking a cue from some fashion-week style setters and the 1983 classic, I’ve filled my shopping cart wish list with the ingredients necessary to become my very own Joel Goodsen.

1. J.W. Anderson cotton-piqué shirt dress: The key piece to this look is the button-down shirt. Whereas an actual oversized shirt accompanied only by undies might be a bit too scandalous for outside-your-house wear, this crisp shirt dress has all of the qualities a white button-down without the potential bum-show—I don’t want to be that risky.

2. Super Basic Sunglasses: Let’s face it, there is no Joel without Ray-Ban Wayfarers. Super’s blue/purple reflective interpretation are both ideal for stealthy people-watching and for use as an always-available, discreet mirror.

3. Proenza Schouler Small Lunch Bag Clutch: While I can’t get behind Cruella De Vil's route to achieving the look, I can certainly get behind the villainess' pension for spotted canine fashion…and, apparently, so can Proenza Schouler. The design duo makes dalmatian accessories a reality with this clutch.

4. Alexander Wang Antonia Sandals: Every girl needs a good pair of black heeled sandals in her closet. These Wangs are high enough to give you a little lift where necessary, but—at four inches—a bit more comfortable and short-dress appropriate than the equally swoon-worthy Saint Laurent heels.

5. Essie For The Twill Of It: With your toes out for the world to see, they need to be primed, painted, and ready for display. Essie’s new fall collection has left me in nail-polish heaven. I'll be reaching for For The Twill Of It to take my toes to mermaid levels of amazingness.

—Elizabeth Brockway

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J.W.Anderson Cotton-piqué Shirt Dress
Super Sunglasses
Super Sunglasses Basic Sunglasses
Proenza Schouler
Proenza Schouler Small Lunch Bag Clutch
Alexander Wang
Alexander Wang Antonia Leather Sandals