WHAT TO WEAR: Vacation

Two days. I have to just two days to pack for college. Be proactive, they said. Start early, they said. Well, they lied. You see, packing for college is easy; you box up your life. Everything you could ever need (yes, that Britney Spears karaoke tape, too) gets thrown into a series of bags to be dealt with at a later date. It’s simple: just bring everything. Oh, and always ignore your dad when he tirades about your clothes not fitting in your two by four. You’ll make it work: #priorities.

Four weeks. I need, without a doubt, at least four weeks to pack for a four-day vacation. My logic? Hello, the word “condense” does not belong in a Fashionista’s vocabulary! A girl has to have options! And what I would do to have a little talking to with the man who deemed that bags over 50 pounds cost more…

Regardless, it’s painstakingly apparent that shoving a vacation appropriate wardrobe into one little bag is not easy feat—it’s a hard one, a very hard one. So, for the fashion community to manage, we must act as smart as we look. We must, dare I say it—condense.

This Fashionista models a few pieces that superbly demonstrate how an obstacle such as the packing dilemma is surmountable. The key is to toss in only transitional pieces that can be used for multiple occasions. Her bohemian style crop top looks care free and breezy with her grungy jean shorts—perfect for a stroll by the marina or around town. Because of the off-the-shoulder nature of the shirt and its horizontal neckline, a simple but short necklace was much needed. This Fashionista’s off-white Van Cleef stunner did just the trick. Jewelry can be difficult with a voluminous shirt such as this, so follow this Fashionista’s lead and try to stay as elegant and dainty as possible with your accessories. Her ring, bracelet and cuff were slight additions that polished off the look without tipping her into gaudy waters.

One Simple Change: The outfit’s simplicity makes it applicable for many vacation settings. The shorts can be tossed on over a bikini for a picturesque walk on the beach or coupled with a plain tank top and fedora for an un-pushed look at the hotel’s brunch destination. But pair that top with printed flare pants and a funky wedge—voilà, you’re beyond ready to go out with the gals and party with the locals.