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).

dark brown black asian hair balayage highlights

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!

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  1. Jean wrote:

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

    Posted 9.22.16 Reply
  2. Nisha wrote:

    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!!

    Posted 9.22.16 Reply
  3. Anonymous wrote:

    Thanks for your reply!


    Posted 9.19.16 Reply
  4. Jean wrote:

    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.

    Posted 9.19.16 Reply
  5. Jean wrote:

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

    Posted 9.19.16 Reply
  6. Jean wrote:

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

    Posted 9.19.16 Reply
  7. Anonymous wrote:

    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,

    Posted 9.19.16 Reply
  8. Menty Yu wrote:

    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 😀

    Posted 9.18.16 Reply
  9. Erica wrote:

    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.

    Posted 9.17.16 Reply
  10. Karen wrote:

    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!

    Posted 9.16.16 Reply
  11. Jean wrote:

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

    Posted 9.16.16 Reply
  12. Jean wrote:

    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.

    Posted 9.16.16 Reply
  13. Jean wrote:

    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.

    Posted 9.16.16 Reply
  14. I love the gray, faded hues in this look. Gorgeous!

    Lifestyle by Joules

    Posted 9.16.16 Reply
  15. Hello, you always look so put together. Love how your outfits look.

    Posted 9.16.16 Reply
  16. Lovely bags for traveling!! 🙂
    ❤️ xoxo,
    Lily |
    PSLily Boutique

    Posted 9.15.16 Reply
  17. 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.

    Posted 9.15.16 Reply
  18. Giselle D wrote:

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

    Posted 9.15.16 Reply
  19. LY NGUYEN wrote:

    Jean ! what mm size is your Hermes belt ?

    Posted 9.15.16 Reply
  20. Emily wrote:

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

    Posted 9.15.16 Reply
  21. Huong wrote:

    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

    Posted 9.15.16 Reply
  22. 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

    Posted 9.15.16 Reply
  23. Love this look and how it's so versatile!!


    Posted 9.15.16 Reply
  24. Deasy Noel wrote:

    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?

    Posted 9.15.16 Reply
  25. Loving that tank!! It'll be great for fall!

    Posted 9.15.16 Reply
  26. Jean wrote:

    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!

    Posted 9.15.16 Reply
  27. Zoe wrote:

    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!!

    Posted 9.15.16 Reply
  28. Love the grey and the belt is the perfect pop of color!

    Posted 9.15.16 Reply
  29. mybeautrip wrote:

    You look great!

    Posted 9.15.16 Reply
  30. Suzie Q wrote:

    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

    Posted 9.15.16 Reply
  31. Ev wrote:
    Posted 9.15.16 Reply
  32. Such an beautiful travel look ! Thanks for sharing.

    Posted 9.15.16 Reply
  33. 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!

    Posted 9.15.16 Reply
  34. You combined your grey denims in such a cool way!
    xx from Bavaria/Germany, Rena

    Posted 9.15.16 Reply
  35. That cognac bag looks so great, I wanna get it!

    Posted 9.15.16 Reply
  36. 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 |

    Posted 9.14.16 Reply
  37. Need those jeans! You look amazing♥

    Posted 9.14.16 Reply

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