Gray Jeans + Ankle Booties // Comfy Airport Travel Outfit

casual travel airplane outfit jeans ankle boots

BP sweater (similar), Express jeans 00 short (updated version), Sole Society travel bag (also sold here) + hat (current version), Sole Society booties sz 5 c/o, Brics suitcase, Dylanlex necklace (similar for less)

I didn’t pack too much for this trip from CA to NY, so have been re-wearing pieces pretty often! This sweater tank in particular has been a comfy layer either over shorts (see un-tucked on me) or jeans, or tucked into skirts which I’ll show later.


I picked out these River ankle booties from Sole Society and they have been my strolling shoes on this trip. The combination of the sleek almond toe, versatile taupe color, and very walkable ~2″ stacked heels make these a winner for Fall (fit was true to size for me). If you usually have trouble with almond or pointed toe shoes fitting narrow on your feet, I’d recommend going up half a size.

travel outfit essentials weekender bag ankle booties

I got so many compliments on these gray distressed jeans, and most friends were surprised to learn they’re from Express! I have denim shorts from there which I looove so figured I’d give their regular jeans a try…

They make a “short” length in many styles, but note actual length will vary from style to style by a few inches. This was the shortest pair I tried on and the denim is stretchy with a wonderfully broken-in feel. It’s borderline too short for my taste, but part of me liked how the raised front ankle opening will be good for showing off higher ankle booties. If you’re any taller than me, I’d suggest trying the regular length unless you want super crops! These are their mid-rise cut legging jeans, which come in a host of colors, lengths, and non-distressed washes as well (see all options in this cut).

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As you can see I wore this exact outfit (at least) twice! I usually bring my Goyard St Louis tote when traveling because it’s so easy to fold down completely flat, and holds a ton when opened up for running errands.

comfortable casual airport travel fall outfit

We’re at the airport now waiting to go home after getting caught in a torrential downpour and missing our flight (NYC traffic during rush hour is no joke!). So excited to sleep in my own bed in Boston!


40 thoughts on “Gray Jeans + Ankle Booties // Comfy Airport Travel Outfit

  • Reply Pamela Gonzalez September 14, 2016 at 9:51 pm

    Need those jeans! You look amazing♥

  • Reply Jessica | Petite Style Script Blog September 14, 2016 at 10:58 pm

    Hi Jean, what a cute travel outfit. I love how you were able to get multiple wears out of it; love versatile pieces and light packing! My favorite part of this outfit is definitely the pop of color with your orange Hermes belt and the Sole Society booties. They look great as a fall staple. They also remind me of the Vince Camuto booties in the mushroom color from last year! I linked those VC booties in my blog post tonight on tweed jackets. By the way, your other Hermes horsebit belt dupe is back at Talbots this season in more classic color schemes, I reviewed the new colors here:

    Thanks for the outfit inspiration Jean!

    ~Jessica |

  • Reply Jane Northey September 15, 2016 at 2:10 am

    That cognac bag looks so great, I wanna get it!

  • Reply Dressed With Soul September 15, 2016 at 2:25 am

    You combined your grey denims in such a cool way!
    xx from Bavaria/Germany, Rena

  • Reply Sophie Spiegelberger September 15, 2016 at 3:56 am

    That suitcase is such a cute statement for travel 🙂
    I post every Monday and Thursday, I would love it if you checked out my blog!

  • Reply Neeltje | Thoughts in Style September 15, 2016 at 4:05 am
  • Reply Marie Ebelt September 15, 2016 at 4:41 am

    Such an beautiful travel look ! Thanks for sharing.

  • Reply Ev September 15, 2016 at 4:44 am
  • Reply Suzie Q September 15, 2016 at 5:09 am

    I didn't expect gray top on gray jeans to be such a chic look, but I love this travel outfit! I love that Express has short option with their pants, I've gotten many of my work pants there. I haven't checked them out in a while, so great to learn that they have good distressed jeans options!

    Suzie Q

  • Reply mybeautrip September 15, 2016 at 5:22 am

    You look great!

  • Reply Kristie Glenn September 15, 2016 at 8:32 am

    Love the grey and the belt is the perfect pop of color!

  • Reply Zoe September 15, 2016 at 9:25 am

    The taupe on the sole society website looks a lot more brown than your photos which look more grey / subtle ? Can you comment which they look like more in reality! Thanks!!

  • Reply Jean September 15, 2016 at 9:31 am

    Hi Zoe! My third photo (the closeup) on here looks most accurate. The lighting in my second photo makes them look too gray. They are a taupe in-person with a hint of gray. Hope that helps!

  • Reply Maggie Zemanek September 15, 2016 at 10:08 am

    Loving that tank!! It'll be great for fall!

  • Reply Deasy Noel September 15, 2016 at 10:31 am

    An almost all gray look suits you very well! And this outfit looks great for traveling, especially in the airport. Do you find jeans to be comfortable in long flights?

  • Reply Sharan Kaur September 15, 2016 at 10:46 am

    Love this look and how it's so versatile!!


  • Reply Tess Felber_Sequins are the New Black September 15, 2016 at 11:21 am

    OH EM GEE I am so obsessed with this outfit!! I just bought that necklace and can't wait to style it! Love your luggage as well 🙂
    xx Tess | Sequins are the New Black

  • Reply Huong September 15, 2016 at 12:05 pm

    I would've never thought of an all-grey look, Jean! This look is so nice and a different change for the upcoming fall season. I really like your pop of color with the Hermes belt too. Thank you for the inspiration! Hope you can get to your bed soon and get some rest! xo

  • Reply Emily September 15, 2016 at 1:31 pm

    Love the gray on gray look…the jeans are great!!

  • Reply LY NGUYEN September 15, 2016 at 6:57 pm

    Jean ! what mm size is your Hermes belt ?

  • Reply Giselle D September 15, 2016 at 9:01 pm

    I was wondering the exact same thing. Thanks for letting us know!

  • Reply denise! [魏穎妍] September 15, 2016 at 9:34 pm

    Hey Jean! I have the same purse. When traveling on airplanes, where do you place your purse? How do you make sure your luxury purses do not get damaged while in-flight? I'm so cautious that I don't trust placing them under the seat in front of me, as convention stands.

  • Reply PSLily Boutique September 15, 2016 at 10:39 pm

    Lovely bags for traveling!! 🙂
    ❤️ xoxo,
    Lily |
    PSLily Boutique

  • Reply syney kitty September 16, 2016 at 1:04 am

    Hello, you always look so put together. Love how your outfits look.

  • Reply Julie Hiller September 16, 2016 at 10:46 am

    I love the gray, faded hues in this look. Gorgeous!

    Lifestyle by Joules

  • Reply Jean September 16, 2016 at 4:50 pm

    Thanks! Hmm, I've only worn them for short flights, but I think they would be comfy as they're very stretchy and not skin tight on me.

  • Reply Jean September 16, 2016 at 4:53 pm

    Hi! I buy pretty durable bags in general (ie. saffiano leather vs delicate lambskin) and take the most durable ones along with me. I think all items will eventually get wear and tear with use so although I am careful, I try not to be too worried over it to the point that I don't use and enjoy them often! One thing you can do though is bring a less expensive, super lightweight foldable large tote like a Longchamp nylon le planetes, and place your designer bags inside. You can then just fold it up into a tiny square after use and put it away somewhere.

  • Reply Jean September 16, 2016 at 4:57 pm

    It's about 23-24 mm wide…not sure what the standard size is!

  • Reply Karen September 16, 2016 at 11:54 pm

    Inspiration hit and I got the jeans today for me and my daughter. I got the short and she fits into the regular! beyond comfortable!

  • Reply Erica September 17, 2016 at 1:44 am

    I actually have been so obsessed with the clothes from Express, ever since I rediscovered them about six months ago. I think they've really stepped up their game, and their XXS and 00S clothes are great for petites! (I'm 5 ft, 105 lbs.) I was very shocked at how well their pants fit, with only hemming needed for the length.

  • Reply Menty Yu September 18, 2016 at 10:38 am

    Love this outfit, and low-heel booties are for sure a smart choice! Maybe you also have a light jacket to fight with in-flight cold air 😀

  • Reply Anonymous September 19, 2016 at 7:57 am

    Hello Jean!

    Great outfit!
    Could you comment on the size of the express jeans? I am a J brand size 23. Do you think the size 00 would work?

    I live in UK, charges shipping and import fees that are not refundable. so i want to make sure before i place the order.

    Best wishes,

  • Reply Jean September 19, 2016 at 9:34 am

    Love that it worked out for both of you! : )

  • Reply Jean September 19, 2016 at 9:34 am

    Same! I'm definitely going to have to check there more often now.

  • Reply Jean September 19, 2016 at 9:35 am

    Hi! Unfortunately I think these will be too big for you. I regularly wear J Brand size 24 and these are not snug on me.

  • Reply Anonymous September 19, 2016 at 4:31 pm

    Thanks for your reply!


  • Reply Nisha September 22, 2016 at 3:03 pm

    Hi Jean,
    I bought these jeans today after seeing them on you in this post. They are SOOOOOO comfortable and I love them So much!! I'm wearing them to a concert tonight actually. So glad I bought these!!

  • Reply Jean September 22, 2016 at 3:44 pm

    Yay! I'm so glad to hear that : ) They are definitely a gem from Express…

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