WHAT TO WEAR: Vacation

I am a notorious over packer. In fact, whenever I used to travel by plane, my dad always made sure I had brought some extra money to pay for the overweight luggage fee. It’s really one of my biggest fears to be in an unknown city or country and not have everything I need. I hate feeling unprepared, therefore I over pack.

Lately, however, I have gotten much better about packing lightly (or as lightly as I possibly can). When I pack, I make sure to spend some time really thinking about what I need rather than aimlessly throwing anything and everything into a bag half my size. When I’m packing for vacation, I ask myself two questions about each item I pack: will it look stylish and will it be comfortable? Whether I will be lounging around the pool under the blazing sun or walking along the streets of a big city all day, I want to look good and feel good.

When I saw this Fashionista, I immediately thought her outfit was the perfect vacation outfit. I imagined her out in the Hamptons, going from poolside to eating out.

A floral dress is the quintessential summer piece. With its square neckline and open back, it becomes more sophisticated than a typical sleeveless dress. It’s lightweight and breathable, and the open back makes it great for super hot weather. A hat is chic and also offers some protection from the sun’s harsh rays. I love how her chunky brown sandals have a tall platform, so that the heel height doesn’t feel quite so high. Light makeup is easy and effortless and won’t melt off in 85 degree weather.

One Simple Change: This outfit can be easily changed to be perfect for traveling. This Fashionista could switch out the wedges for some stylish sneakers while traveling on the train. She could also bring along a denim jacket for the ride in the chilly train car.