Why Dresses Are My Go-to Flight Outfit, Even in Winter

  • My go-to flight attire is dresses, even in the wintertime.
  • It helps me to feel comfortable, confident, and stylish when traveling.
  • It’s also practical for short-haul flights or flights where you will land in the morning.

When packing clothes for a trip, the first thing I consider is what to wear on the flight. 

I’m not a fan of sweatpants or leggings, and jeans are often too restrictive to wear for extended periods. My priority is comfort and style — which is why dresses are the perfect choice, even in the wintertime. 

Dresses help me feel confident and comfortable

In my opinion, dresses are a particularly sensible choice for short-haul flights or flights that land in the morning.

Many hotels don’t allow guests to check in until the afternoon, which means that oftentimes I’ll have to wait to freshen up until later. I’ll often find myself leaving my luggage with the hotel’s concierge before heading back out to explore, grab a bite, or kill time until my room is available. 

mikhaila sicily dress

The author is pictured in her hotel room after landing in Sicily, Italy.

Mikhaila Friel/Insider

When this happens, I like to look as put-together as possible — especially if I’m planning to take photos at visitor attractions.

Of course, it’s different for everyone, but dresses help me to feel my most confident. 

Choosing the right dress is essential

My top tip is to find something that helps you to feel at ease and comfortable during the flight, and also something that works for the season you’re traveling in.

Each to their own, but you’ll never find me in something form-fitting, short, or restrictive when flying. Find what works for you and your comfort level. 

When traveling in the summer, I’ll most likely opt for loose-fitting and flowy dresses. During a flight from London to Sicily earlier this year, I wore a floral-print midi dress with short sleeves. 

When traveling during the winter, my favorite thing to wear is sweater dresses, which are incredibly cozy and warm. You get the practicality of wearing knitwear, and in my opinion, this garment completely levels up a winter wardrobe. 

If sweater dresses aren’t your thing, I’d advise you to pack extra layers. When traveling from Glasgow to the Island of Barra in Scotland in September, I opted for a button-down, polka-dot dress with tights, pink boots, and a tartan shawl. The shawl especially came in handy, as I was able to wear it with other outfits throughout the trip. 

Clothing is subjective, especially when it comes to flight attire. If dresses work for you, that’s great. 

But if not, I’d encourage all travelers to write down what is important to them while flying, and look for clothes to match the list.

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