top of page

I Woke Up (At 2:30 A.M. + Got Ready) Like This


Airplanes. Traveling. Airports. New Destinations. All such magical words. That is, until you look at your itinerary and see a flight departing at 4:45 a.m.

I am not a morning person. In fact, I’m so much the opposite that I’m nearly convinced I’m a nocturnal human being. Seriously. My prime time for getting stuff done is around 11 o’clock at night, meaning my bedtime tends to be dangerously close to the time my alarm goes off in the morning. At the beginning of this trip, the two were basically synonymous. Needing to be at the airport by 4 a.m. to go through security and get checked in, plus a half an hour of travel to get there and some time to look halfway decent, put my approximate time to hit snooze at about 2:30 a.m.

Luckily, I did myself one favor and picked out my travel outfit the night before we departed. Considering how long it can take me to decide what to wear, this was a huge time saver.

One of the biggest things to remember when choosing a look for the airport is comfort. You already know you’re going to be stuck in a seat with minimal leg room and no space to adjust how you're sitting. Even worse, you might have to get up seven times for the guy beside you. The only thing you can do to make life a little better is wear something comfy, like these cloth shorts. Since they’re made of light material, they are easy to move in and don’t get messed up by sitting for hours. Honestly, they feel like you’re wearing athletic shorts, but they look like you put in a lot of effort.

The second thing to remember about traveling is that planes are inevitably cold. I’d consider myself pretty cold-blooded, so I don’t complain about chilly temperatures too often, but airplanes always throw me for a loop. If I’m caught in shorts, sandals, and a tank, I will be covered in goosebumps within seconds. In an attempt to combat being frozen, I opted for this striped, long sleeve button up, rather than a typical summery top. Together, the pair screamed East Coast casual, which was the perfect look for arriving in Boston.

To avoid the hassle of airport security, and to add a little color to the blue and white palette, I slipped on these red sandals. When I initially purchased them, I didn’t know if the color would clash with too many things, but truthfully, I’m almost beginning to think that this coralish-red color is a neutral. It seems to work with everything in my wardrobe, in particular black, white, and blue (#Merica). As a bonus, they’re incredibly comfortable for walking, which made them a great choice for a day of sightseeing.

As for the wrist-ware, I tend to shy away from bracelets. They always slide up and down my arm, but for these two classics I make an exception. The bracelet, an Alex and Ani, ties in the gold from my necklaces, while the vintage (probably fake) Fossil watch just completes any outfit by making me grin. I had been on the hunt for a map watch for ages, when I stumbled upon this one at a flea market in Mesa, Arizona. Now, I throw it on whenever I want to put a smile on my face, something I desperately needed at 2:30 a.m. To finish off the accessories, this brown bag worked as a functional carry on, as well as the perfect neutral for matching several outfits on the trip. When packing, it’s crucial to capitalize on multiple uses.

So, there you have it. My perfect plane ensemble for early morning flights, keeping me both comfortable and warm. Not to mention, it was cute enough to be a tourist in too, since we hopped off the plane at 10 a.m. Boston time and had a whole day of wandering through the city streets. Next time you see 4:45 a.m. on your travel itinerary, you're one step ahead of the game. You have an outfit idea already in place!

Be sure to be on the lookout for OOTD’s from my entire vacation over the next few weeks. You won't want to miss out!

sending you all my love

xoxo madison

SHOP THE LOOK

Shirt (similar):

Shorts (sold out of denim):

Shoes:

Compass Necklace:

Purse:

Fossil

'M' Necklace (similar):

Bracelet:

Watch:

Flea Market

bottom of page