We’ve all been there: you want to look like you’re heading straight to a luxury resort, even if you’re actually just heading to Gate B12. The goal is to find that perfect balance of TSA-friendly “quiet luxury,” outfits that are sophisticated enough for touring your destination but comfortable enough for a long-haul flight. Whether you’re navigating security or hitting your first few tourist stops before hotel check-in, your look should be effortless, not fussy. After countless miles, I’ve mastered the art of the expensive-looking airport outfit. Here is exactly what I wore to stay stylish and cozy through both early spring and winter weather.
Early Spring Weather: The “Monochrome Set”
The fastest way to look expensive is to remove visual “noise.” When you wear a matching top and bottom in the same shade, it creates a seamless, tailored look. I don’t care what your GenZ kid tells you, it’s still ok to wear leggings in a monochrome set, especially when you are in for a long haul flight and then this maneuver on a moving water taxi in Venice, Italy upon arrival.
Here I am wearing this OGL Thermal Mockneck top and these Kuhl leggings.
I am also wearing a simple black vest like this one.
These Clark zip up sneakers are the ultimate in TSA friendly minimalist style and oh so comfortable. I have worn these all over Europe and can say they pass the 20,000 step test.
Fun fact. I do not use a traditional carry-on, rather, I use a duffle style bag I can keep under the seat in front of me. I try to keep it as empty as possible on the flight over and tuck my purse into it, using only one personal item. Then I have room for purchases I know I will make during the trip. This Wedama Weekender Bag is the type of bag I would carry with this outfit.
Winter Airport Outfit: Warm But Not Bulky
I traveled to Iceland in March and knew I was going to be touring before we checked into our hotel. That meant I needed to be ready for the weather and looking stylish on the way over while not feeling like a sardine in a can in my airplane seat. Here’s the outfit.
Those look like trendy wide leg jeans don’t they? They are sweatpants with an elastic waist. I found these DLOODA Women’s Wide Leg Jeans that are very similar and affordable. Chef’s kiss.
If you read my blog you know I LOVE OGL tops, especially their pro warm turtlenecks. I paired these jeans with one of my favorite versions of their turtleneck for the flight.
This puffer jacket is very warm and lightweight. I was able to roll it up and store it in my duffle carry on, then put it on when I arrived in Iceland.
I opted for TSA friendly Clark boots for the flight over, knowing I would be in the city the first day. My serious boots were packed in my suitcase.
I carried a MHCNLL Crossbody weatherproof bag as my personal item and tucked it into the same duffle above. It has lots of pockets and room for a water bottle for that famous Icelandic water too.
Travel Packing Strategies
My overall airport packing strategies tend to be minimalist, keeping colors to neutrals, wearing clothes with slim profiles and wearing layers. If you’d like to see complete packing ideas for trips like Italy, Iceland, Greece, Scotland and more, visit my travel packing tips here. I’ll see you on the next trip!