Following a recent trip to London I took with my four kids between Christmas and New Year’s, I’ve decided that I totally spend as much – if not more – time obsessing over what to wear on the plane than when I’m on the actual vacation.

Unlike most other outfits I’d need to pack for our vacation – clothes for touring the Tower of London or enjoying an elegant tea with my daughters – my travel ensemble needed to serve a number of functions.

First and foremost, it needed to be cozy enough for a seven-hour overnight flight in coach that would allow sleep. Critical. The outfit also had to take me through a day of sightseeing once we landed. And finally – and most importantly – I obviously also wanted to look cute and not like I was a crazy person walking around in my pajamas.

No problem.

The other critical piece to the travel puzzle – because it is a puzzle, n’est-ce pas? – was figuring out what accessories would help facilitate my goals. I needed a bag and shoes that would encourage comfort whilst preventing me from looking like the Ugly American (and I was already planning on walking around with my camera around my neck for most of the trip).

In the end, I think the weird amount of time I spent thinking about these things paid off. I slept a good amount of the flight (thank you, Valium), spent a day hopping on and off the Big Red Bus and a spin around the London Eye at dusk, and – because we were so exhausted by the end of that first day – stayed in my travel outfit for dinner at a gastropub around the corner from our hotel. At the end of our meal, the owner sent us over glasses of champagne to celebrate our first night in London and I can’t decide if it’s because he was delighted with how chic we all looked or felt sorry for our sad state of affairs.

Needless to say, I peeled that 24-hour outfit off that night and thanked it for its service. It had done its job.

ONE: Cardigan/Garnet Hill; TWO: Blanket Scarf/Mark & Graham; THREE: Travel Blanket/Sac; FOUR: Leggings/Athleta; FIVE: Passport Holder/Cuyana; SIX: Boots/Clarks; SEVEN: Sports Bra/Athleta

1. Cashmere Cardigan: As a 50-year-old lady who is prone to feeling like her hair is on fire at any given moment, I am an advocate of layering – with cashmere, where appropriate. Honestly, it’s like wearing a very cozy blanket. Throw over this cute tank and you’re ready for your nap.
2. Blanket Scarf: I bought these big, soft scarves for my daughters for Christmas that doubled as cozy throws for the flight. I am also now completely devoted to the site because I not only nabbed them at Black Friday prices but the free gift wrapping they arrived at my door in seemed almost more expensive than the scarves themselves. Well-played, Mark & Graham.
3. Travel Blanket/Pillow: I’ve had this cozy set for years and it’s come with me on all sorts of adventures like Greece and Hong Kong. Even though they hand out blankets in sanitized plastic wrap for longer flights, I’d still rather know where my pillow has been.
4. Leggings: Okay, I currently work at the store but even if I didn’t, I’d still rave about these tights. They have just the right bit of compression, cute zippers at the ankle and the waist is nice and high and doesn’t cut into your midsection while you’re cramped in your seat mid-flight. Plus, it kinda just smoothes out the whole middle situation, if you know what I mean (see 50-year-old lady bit above).
5. Passport Holder: I honestly didn’t know I needed a passport holder until my BF gave me this chic little number for Christmas. The soft leather has this wonderful pebbly grain and my initials embossed in gold on the bottom corner. It ended up being the perfect wallet for a trip abroad, where you’re really only carrying around your license, credit card and some currency. You can leave your Costco card at home.
6. Black Suede Boots: At one point in early December, it looked as if my bedroom was doubling as a Zappos warehouse. I just kept ordering boots that I thought might fit the bill of being comfortable to walk all over London and yet not make me look like too much of a granny. I mean, I do have a reputation to uphold. In the end, these babies from Clarks made love to my feet all day long. There’s really no other way to say it. And their looks kinda grew on me throughout the trip, even after my younger daughter observed during our Harry Potter Warner Bros. Studio Tour that they somewhat resembled the Sorting Hat. Maybe that just makes me a wizard.
7. Sports Bra: This should really have made it to the top of my list because I spent so much time thinking about finding the right undergarment for sleeping and sightseeing. I only wish I’d discovered this bra before my 16-hour flight to Hong Kong a couple of years ago because it’s so comfortable. In fact, now that I’m home, I still find myself throwing it on most days instead of a regular bra with wires and hooks. Imagine me like Oprah right now freaking out over bread: You MUST have this bra! GO GET this bra!
8. Cross-Body Bag (Not Pictured): Need a great bag for sightseeing that’s also super-stylish? Go buy this bag from Madewell right now. Yes, I’m still talking like Oprah.
9. Book a Trip!!: You say you have nowhere to go! It’s not too late to book a spring break getaway! You can still snag a fabulous rental someplace warm through Tripping.com, which is kinda like the Kayak  (my flight/hotel fave) of vacation rentals. It’s one-stop-shopping for rentals listed on all the top sites like TripAdvisor, VRBO and Homeaway. Don’t know where to go? We hear Florida is the hot destination du jour (in more ways than one). Get booking!

Stop being so greedy already! Share your own travel must-haves in the comments below. You’re the best. Sign up to get all of my latest posts sent right to your inbox by typing your email into the box below and new posts will arrive without you having to remember to look for them. Everything should be this easy. You can also follow me on Facebook, Twitter, Instagram and (what the hell) Pinterest. [wysija_form id=”1″]