The Perfect Airplane Outfits

It’s not easy to look good while traveling by plane, especially on those long overseas flights. I know some women who seem immune to the discomforts of flying, whose airplane outfits look just like what they normally wear. But like many others, I suffer from being too damned cold on the airplane and wanting to actually be comfortable.

With many long flights under my belt but no really successful airplane attire, I have recently been putting together an outfit to wear on my upcoming flight to Italy.  The way I see it, perfect airplane outfits need to have the following characteristics:

  • comfortable
  • warm but not bulky
  • with layers that can be easily added or discarded in case of a warm airport or cold flight
  • stylish because when you’re traveling, especially to other countries, you are making a statement
  • with more than one purpose; in other words, I must be able to use all the pieces during the whole trip, not just on the flight

The quest for the perfect airplane outfit begins with the right pants…

After many uncomfortable overseas flights that always included the wrong pants, I finally decided that I would find and buy “airplane pants.” That term may not exactly sound stylish, but a lot of thought went into what these airplane pants would comprise. I knew they should be comfortable but cute, a dark color, fitted, and able to worn not just on the plane but during the whole trip.

I finally found perfect leggings for travel from Everlanethe perfect pair of black pants, the Richmond pant from Boden, or the most comfortable pants, the Martie pant from J. Crew in black. A pair like this should fit perfectly and be stretchy enough to accommodate sitting on the airplane but not stretch out at all, even after wearing them all day. Plus, they’re machine washable and can be thrown in the dryer without losing their shape.

Perfect Airplane Outfit: Fitted Pants | This Is My Happiness

Pants like these are not just comfortable and stylish for the airplane–they can easily be paired with just about anything for day or night while traveling.

Now, what goes on top? One would think that this would not be so difficult, but there is more to it than meets the eye, especially if you get cold easily like I do. Followers on my Facebook page suggested the following: something dark in case of spills, something comfortable (duh), something warm (yes!), and something made of soft or natural fabrics. I especially recommend a warm cashmere sweater for travel, like the cashmere at Everlane–high quality and reasonable price.

cashmere sweater for travel

I agree with all of those suggestions, but I add the following touches: a necklace, a fun scarf for added warmth and color, and a tank top underneath.

What about shoes for the airplane?

This is not easy because I need something comfortable. See my suggestions for cute and comfortable shoes for travel, such as desert boots, these comfortable flats, and these stylish sneakers.

cute travel shoes

I’m also a huge fan of Birkenstocks for travel and like these closed toe Birkenstocks as a comfortable travel shoe for airplanes.

And the perfect travel bag?

Well, this one is still in the works. I’m still looking for the perfect airplane bag, but here are some good options:

Ona camera bags: the best camera bag because it looks good, it’s leather, and it really holds all your photography equipment

best camera bag

Eagle Creek: the best small rolling suitcase (duffel): Eagle Creek products are made for travelers and are made to last. Highly recommended.

Kenneth Cole travel bag: Best airplane travel bag? This bag seems to be the perfect option for airplane travel as it has a space for everything, including a laptop. My only complaint is that it’s not real leather, but hence the sale price of $49 (it was $180).

So there you have it! I think I have the ultimate warm, comfortable, but stylish airplane outfit. Now it’s your turn: what are your tips for great airplane attire?

More ideas: 8 Items I Never Travel Without


  • Cathy Carson says:


    Check out the Fat Hat Clothing company . They have wonderful clothing for travel. i have a wardrobe of their cotton down sweaters.

  • Cindy says:

    Thanks for the great post, Jenna! It was timely for me because I’m leaving Wednesday on a long flight to New York.

    Can’t wait to hear about your week in Florence!

  • Ayngelina says:

    I am constantly in search of the best outfit. I want to wear yoga pants but I feel compelled to look a bit more polished, I like what you’ve picked.
    Ayngelina recently posted..Faces of Crow FairMy Profile

    • Jenna says:

      Thanks. Let’s see how the pants hold up. They look nice on but I’m not sure if they will stay that way after some wear.

  • Charu says:

    I love how you’ve selected so many black pieces…you’re practically a New Yorker! Love the versatility of the sweater, I must say. I always carry a pashmina or throw with me too, because I get very cold on the flights.
    Charu recently posted..In SoHo, a Forgotten French Pastry Gets a Second LookMy Profile

  • Sonja says:

    This is a never-ending struggle with me. At least you don’t have to deal with a heavy-set figure on top of everything else, like me! The shoes are a nightmare – if you wear sneakers you are instantly pegged as an American and look unattractive as well. I’ve tried Converse (since they’re “hip” sneakers) but found them uncomfortable, too. Boots can be comfy and warm, but not wearable for summer traveling. Erg.
    Sonja recently posted..Magical MittenwaldMy Profile

  • Your airplane pants look a lot like my airplane pants:P For shoes, though, since I like to be able to slip off and on (and am usually expected to do so at security) I wear Blundstones (boots from Australia, the low-rise version). They are waterproofed leather, nice smooth profile, not overly warm but can be made warmer with thicker socks. Considering winter in Italy (and England, and…) usually means more water than snow, I find Blundstones ideal. It’s a very old company, still making a very good product.
    Lesley Peterson recently posted..Lagoon dreams: Venice, Burano & TorcelloMy Profile

  • I definitely can’t speak for outfits for a woman. Heck, you’ve seen my post about what I wear on planes and why I took my pants off 🙂 I am not one you ever want to get fashion advice from – even in a plane 🙂
    Jeremy Branham recently posted..The Army Navy football game: United we stand, divided we playMy Profile

  • Dalene says:

    3 years on the road now and I’ve finally landed on the perfect outfit for me – summery cotton dresses. Add long sleeves and tights for winter, and then can wear them on their own for summer (which is good because we switch climates a lot!) And it is SUPER comfortable for the plane! 🙂
    Dalene recently posted..Be Kind to TravelersMy Profile

    • Jenna says:

      GOod idea about putting a shirt under it. You could pair it with warm leggings for colder weather, too.

  • Rosa Summers says:

    I have a pair of soft khaki tannish cropped pants, that I love to wear on airplanes. With family in the UK I fly often. I wear my black toms; I have a stripped tank and a black button up to go on top and a black cardigan. Soft, comfortable, and classy. I always take in my carry on: extra undies and socks, eye liner, hairbrush, and my own concoction! I take a small spray bottle, get a moisturizer and dilute it with water. So all I have to do is spray my face and voila! I have a nice face cleanser and moisturizer! ALWAYS pee before your flight, just added advice…. lol

  • Well, I understand the importance of perfect outfits needs while traveling in plane. your idea’s over airplane outfits are very interesting and useable. shoes are also looking very comfortable for such conditions.
    Miranda Gahrman recently posted..Make a Winter Fashion Statement: Coats and Jackets for WomenMy Profile

  • Kellie says:

    That’s almost exactly how I like to dress for travel too. The only difference is I don’t wear shoes that tie. Such a hassle to take off and on for screening. Comfortable flats is the way for me.

    • Jenna says:

      I try to go for Mary Janes so that I can slip them off, too. I’ve been looking for the perfect pair of comfy flats.

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