One of the best and worst parts of traveling is that you can't take all of your things with you. It's tough to know exactly what you'll want to wear, what the weather will dictate (I must have packed eight summer dresses that I've ignored in favor of my rain slicker), and the items that will be the most adaptable. It's a challenge that I secretly love - and one that reinforces the idea that you only need a few key pieces each season to completely punch up your wardrobe. Here are the three items that are currently at the top of my list. 1. Silk striped dress. A classic pattern in a versatile silhouette that's as well suited for a graduation as it is for a date night. During the day, I'd wear it with a straw hat, loose waves, an armful of bracelets, and neutral sandals. At night, I'd pull back my hair in a low knot, wear a tuxedo jacket, strappy heels, and a sequined clutch. 2. Crisscross sandals. These are plain enough so that you can throw them on with nearly anything, but with enough detailing (I love the toffee-colored leather paired with the pop of pink) to make them special. During the day I'd wear them with jean shorts, a plain t-shirt, and a blazer. At night, they'd be the ideal complement to a '60s-inspired shift dress with a sleek blowout and a nude lip. 3. Horseshoe necklace. In warmer months, I gravitate towards simple, delicate jewelry that looks good on its own, or layered with other pieces. During the day, I'd wear this with a few longer gold chains, a bright tunic, skinny jeans, and wooden wedges. At night, I'd wear it with a strapless nude-colored dress, a high messy bun, and simple platforms.