Last year, I was on upwards of 20 separate flights. And with all that traveling, I had to learn how to pack properly.

When I first started traveling on my own in my early 20s, I’d make terrible packing decisions. I threw everything but the kitchen sink into my big red suitcase, trying to make sure I was prepared for any situation. But inevitably, I’d get to the end of my trip and realize I hadn’t worn even half of what I’d packed. My biggest sin of all became increasingly obvious with the shoes I’d drag along. Boots, wedges and heels easily took up half of my suitcase.

While I made the effort to set my ridiculous variety of shoes out and did occasionally slip them on for a few hours during a shoot or party, the rest of the time they just sat in hotel rooms, sad and unworn. I was making packing decisions that put form over function and I wasn’t doing myself (or the taxi drivers hoisting my suitcase out of their trunks) any favors.

This year, I finally got my shoe game sorted. Throughout the first few months of 2014, I packed a pair of black boots and a pair of black sneaker wedges through the winter and spring. That was easy enough but I’ve still been stumped about what to do for the summer months as a three week trip to Europe quickly approaches.

Enter Trask. As some of you may know, in a past life I worked at comfort shoe stores. And occasionally, this brand would pop up in conversations. I wasn’t super familiar with it since Trask had been shuttered years before but my customers consistently raved about the quality. So when Trask recently popped back up in the shoe landscape with a brand new women’s line and reached out, I was game.

I want to be stylish yet comfortable as I travel through London, Berlin and Amsterdam soon and not worry about tripping over cobblestones! The answer? Piper ballet flats. They’re lightweight, comfortable and sturdy which is my holy grail when it comes to picking out new shoes.

Along with the Pipers, I’ve rounded up some of my other travel must-haves:

1. Unique Basics. I usually stick to a palette of mostly black and white clothing so everything mixes and matches. To keep it fresh, I add in a few fun prints like this Carrie Hammer newsprint skirt. 2. Comfy shoes. Sightseeing sucks when your feet hurt! I plan on sticking to comfortable, basic ballet flats like the Piper. 3. Pencil or pen. Gotta be prepared for that next brain wave! 4. Magazines. I always have an unread stack in my office and the plane is the perfect time to get caught up. 5. Fun Jewelry. Because I pack mostly black and white clothing, I add in a few fun necklaces to liven up my looks. 6. Passport. Enough said! 7. Book. I fly through the 2 or 3 magazines I pack at warp speed but carrying more than that isn’t an option. A good paperback book lasts longer and doesn’t add much weight. 8. iPad. It’s perfect for movies on the plane and music playlists in my Air bnb pads. 9. Colorful Lipstick. I only pack the basics when it comes to makeup since cosmetics get heavy really fast. To keep things fun, I pack a few coral and orange-toned lipsticks. 10. Favorite Perfume. I finally found a signature scent! I roll it up in a sweater inside my luggage to keep it from shattering. 11. Hand Lotion. The soap in all those airport and restaurant bathrooms sucks out all the moisture. I love Grown Organics Vanilla & Orange Peel lotion. 12. Notebook. I like to make handwritten notes and lists on the go. 13. Light layers. Because the weather can change so dramatically, it’s important to layer up. I usually wear a black tank and then layer something fun like this sequin polkadot top, add a cardigan over that and then finish it off with a lightweight leather jacket.

***THIS GIVEAWAY IS NOW CLOSED.***

Enter To Win

Now that I’ve got my packing sorted, I want you to have the chance to try out the Trask Piper ballet flats for yourself! One winner will receive the Piper in black lamb / calfskin in their size.

To enter the giveaway, answer this question in the comments:

What would be your dream vacation to wear these flats on?

Make sure to include your name and email so I can contact you!

The contest is open to U.S. residents only. One winner will receive a pair of Pipers in the size of their choice. The contest is open to everyone over the age of 18. You have until 11.59 pm on Thursday, June 26th, to enter. Winner will be contacted after that date via email and will have one week to email me their address to claim their prize. The prize may not be exchanged or transferred and no cash alternative will be offered. Liability cannot be accepted for entries which are lost in transit or not received due to technical difficulties. No purchase necessary.