Dressing to Get Upgraded at the Airport: Style Sweet Spot

Dressing to Get Upgraded at the Airport: Style Sweet Spot

The way some women dress for airline travel surprises me. I’m not talking about the young mothers hauling car seats, a double stroller and two children under 4. I’m talking about midlife women who dress as though they’ve just come in from gardening all day. Or worse, just rolled out of bed. They want to feel comfy and I applaud that. Travel is tiring. I always want to dress comfortably. There are ways to dress for airline travel that will get you the service and respect you deserve, and not look overly casual.

Hit Your Style Sweet Spot

Style has the power to transform your confidence. Working from the outside in, women can boost their confidence by hitting their Style Sweet Spot. Pam Lutrell and I began this new series, Hit Your Style Sweet Spot, to help and inspire those women who are struggling with their appearance. Each week we choose a scenario from our daily lives to show why, what and how we dress to reach our style sweet spot. Your style sweet spot is when you feel confident about your appearance and know you are sending the message you want people to see.

Last week Pam and I showed how we dress in black and white, today we are sharing how we dress for airline travel.

Traveling in style doesn't mean being uncomfortable.

This week the scenario is true for me. I flew to Mexico this morning and here’s what worked for me.

I ‘ve gotten upgraded by airlines many times. I’m convinced part of the reason I’m chosen is because I dress nicely to travel. That doesn’t mean I dress up but it means I don’t wear sweats, pajama bottoms with a T-shirt, flip-flops or shorts. In fact, I don’t own shorts, but that’s a whole other topic.

Garments with lycra or spandex needn’t be overly casual. Everything I wear for travel has some stretch built into the fabric.

This shirt by Comfy, is loose but has an interesting shape that makes it fun.

Wearing your largest hat is the easiest way to get it to your destination.

These pants by Babette have lots of stretch but the interesting texture steps up it’s formality. Just a bit!

I’ve found wide leg pants are a hassle to keep off lavatory floors so I stick to narrow legged ones.

These Babette pants have the perfect amount of stretch, yet look updated.


I’m lucky to be traveling TSA Pre this week so I don’t have to remove my shoes at security. If I wasn’t, I’d wear shoes with socks. Being barefoot in the airport is just gross.

I wear my largest hat for traveling, because it’s the easiest way to get it where I’m going. Since I never check a bag, my carry on is a bit small for this hat.

My carry on always holds a wrap for when the airplane gets to refrigerator temperatures.

Having lycra or spandex in these fabrics allows me to arrive unwrinkled and looking polished.

Now let’s pop over to see how Pam hits her Style Sweet Spot!


Pam Lutrell, Susan Street and I have an upcoming Blab scheduled on Tuesday, March 29 at 10am, PST. HERE is the link to subscribe and join or watch later. We hope to see you then!

When Are Women Over 50 Dressed too Casually-

I am away on holiday this week so will be posting sporadically, if at all.

I need a rest. My body is telling me it’s time to decompress. I expect to be on Instagram because I love to capture photos. Join me there and have a great week!!

xo Jennifer




This post may contain affiliate links which won’t change your price but will share some commission.


  1. Darlene
    April 28, 2017 / 12:23 pm

    I would love if you could show what you took to Mexico as far as a wardrobe goes ( I believe you said it was going to be taupe and white). I am desperately trying not to take my whole closet with me ( carry on only) but have trouble eliminating things to take with me. Any help would be appreciated!!!

    • Jennifer
      April 28, 2017 / 5:41 pm

      This is an older post, and I have since gone again, with just carry on. Here’s what I packed this year, 3 cotton maxi skirts, two cotton cardi’s with sun protection, 3 nice tops, 3 t-shirts, 2 tank tops, 1 pair jeans, 3 pair sandals, 4 sunhats, and 1 bathing suit. I mix and match for different looks. I limited my colors to black, white and blues. This allowed me to mix and match. Do not take too much. Mexico is casual and you can re-wear dinner out looks several times.

  2. April 9, 2016 / 1:44 pm

    How have I been missing these posts? So glad to find this today. 🙂

    We have a good friend who was a flight attendant for 20+ years. She used to always talk about the way they would people who were well dressed for first class bumps. Why do people want to go places in their pajamas? Yuck!

  3. March 31, 2016 / 2:17 pm

    Well don’t you look totally fab for airplane travel. I’m headed to Hawaii soon and I think I’ll wear my big giant hat on the airplane – I’ll look chic like you and it won’t get crumpled!

    • Jennifer
      March 31, 2016 / 11:09 pm

      That’s the best way to get it to Hawaii!

  4. March 31, 2016 / 10:17 am

    Good advise. I add a pair of socks for the plane too for the “refrigerator temperatures” 🙂

  5. March 31, 2016 / 10:05 am

    Great advice and inspiration! Thanks for sharing this post at the Thursday Favorite Things Blog Hop . . . we all need some advice and guidance once in a while and I love your style! Nina @ Vintage Mama’s Cottage

  6. March 31, 2016 / 4:46 am

    Well, don’t you look sharp! These are great tips, and I’m with you…traveling next to someone in their pj’s with stains or their undies sticking out the top is all too common. I wish more folks would consider others before boarding an airplane! Lol!

    • Jennifer
      March 31, 2016 / 7:28 am

      Great point about considering others before you dress for airline travel! Deodorant is a must!!:)

  7. Rattlebridge Farm
    March 30, 2016 / 7:38 pm

    I loved this post! I once wore a stretchy dress to Paris, and before we left Atlanta, I’d had a wardrobe malfunction (late for the plane; dress rode up, Big mama panty hose beneath. TI still relive that night. I’m going to look for a classic white blouse and slacks.

    • Jennifer
      March 31, 2016 / 7:29 am

      Oh oh. Funny now, not then I’m sure. Panty hose are so uncomfortable most of the time!

  8. March 30, 2016 / 6:29 pm

    I LOVE the pop of red! It always looks so fresh, and classic. 🙂

    • Jennifer
      March 31, 2016 / 7:31 am

      I love red too. It doesn’t look good on me so this is how I get to enjoy it.

  9. Gayle
    March 27, 2016 / 12:41 pm

    We upgrade with points, the list is soooo long these days that there don’t seem to be any upgrades because of any other reason. Love the outfit and dress similarly

  10. March 25, 2016 / 8:28 am

    Very good tips. I also disike when people dress too comfy on the plane. For me, it’s very disrespectful. I love the whole look of yours and the hat stole my heart!
    Happy Easter!

  11. Regina L. L. Wells
    March 24, 2016 / 8:36 am

    I avoid air travel at almost any cost and haven’t been on a plane or in an airport in 10 years this fall, but I had to read this post, Sue. Good advice here. (Although I will admit to travelling in everything from shorts and a tank to a full suit, hosiery, and heels (depending on where I had to be when I disembarked.)

  12. March 24, 2016 / 12:20 am

    Good luck with the upgrades! The only upgrade I’ve ever had is to the emergency exit aisle, but maybe I need to take off my DVT socks and put on a gorgeous hat!
    Happy holidays
    Wren x

  13. March 23, 2016 / 7:30 pm

    You look smashing! Happy travels, and come back refreshed. Hope to see you at BAM! xoxox, Brenda

  14. March 23, 2016 / 9:45 am

    This looks like the perfect travel outfit, Jen! You are SO right about wide leg pants and bathroom floors–ugh! I’m packing today and heading off to a little island in the Caribbean. Perfect timing to read this post!
    I hope you are having a most relaxing getaway. Time to decompress and take some time for yourself.
    Let’s toast each other from on Thursday night from our tropical getaways!

  15. Deborah Montgomery
    March 22, 2016 / 3:06 pm

    I remember an old episode of Andy Griffith where they were flying to California and Opie and Andy wore suits and ties, and Aunt Bee had on a hat and gloves, and of course a dress. I always think of that when I travel!
    Have a great trip.

  16. March 21, 2016 / 10:59 am

    I hate the bare feet in the airport thing too. So uncivilized. You look very smart when you travel!

  17. March 21, 2016 / 6:11 am

    I totally agree with you! I am on planes a lot right now, and am shocked at how people dress to fly. I remember when you had to dress up to fly!!! I can’t get over the pajama thing. I like to be comfortable too, and your suggestions are just right!!!

  18. March 20, 2016 / 9:06 pm

    Love that hat! You look chic and comfy. I cannot wait to hear about this trip. I agree people are way too casual.. Don’t even get me started on the pj thing. xo Kim

  19. March 20, 2016 / 5:59 pm

    I agree. It is important to look nice, not sloppy when traveling. I am a white shirt addict so my go-to travel uniform tends to be nice jeans and a white shirt. That way the jeans don’t take up space. We travel in the fall quite a lot-usually cold here and warm at the destination. Last fall I found a snuggly sweater jacket which worked perfectly as my coat on departure and return and as a blanket on the plane!

    • Jennifer
      March 20, 2016 / 7:35 pm

      So true Laura! The jeans take up a lot a space. Your sweater jacket sounds perfect.

  20. March 20, 2016 / 5:34 pm

    I hope you have a WONDERFUL trip!

  21. March 20, 2016 / 4:51 pm

    You look great. I always like to look nice and chic because it makes me feel good and I never know who I may see or who may see me.

    • Jennifer
      March 20, 2016 / 7:33 pm

      Thank you! That’s what counts for me too! It helps me feel good.

  22. March 20, 2016 / 2:29 pm

    My travel demeanor was established by my frequent business travel during my 20’s, 30’s and 40’s. To me any travel is special, therefore I dress comfortably chic. Sadly over the years the service and standard of dress in the cabin has diminished to the level of riding a bus. Have a wonderful holiday, Jenn! Enjoy your moments “unplugged”!

    • Jennifer
      March 20, 2016 / 3:00 pm

      Great analogy Lynne. Bus travel attire is more like what I’ve seen lately at the airports. Xx

  23. Debbie Z.
    March 20, 2016 / 2:27 pm

    Jennifer, I have just just discovered your blog and am enjoying it so much. Thank you for all the tips. Could you tell me where that white shirt is available? I am not seeing where I could click on a link or anything like that. Thanks.

    • Jennifer
      March 20, 2016 / 2:59 pm

      Hi Debbie, welcome! There is no link because I’ve owned this blouse for several years. The brand is called Comfy USA. It’s sold on Amazon and several other shops online as well as boutiques. They seem to reissue this blouse in different colors every so often. If I find it, I will email you a link.

  24. March 20, 2016 / 2:16 pm

    The hat is great! I’m glad you mentioned where it’s from because I’m on the lookout for another hat to take to Europe this summer.
    We traveled a lot as a family when the children were small as we worked overseas. I always made certain everyone was well-dressed.
    I find skirts easier to travel in than pants (fuller, midi length or longer). I’m with you on the socks and shoes – I once had to take off my sandals and walk through the scanner barefoot. Yuk!

    Enjoy Mexico!

    • Jennifer
      March 20, 2016 / 3:02 pm

      Thanks Lorrie. I agree skirts are more comfortable and easier.

  25. March 20, 2016 / 11:43 am

    Nice outfit. I agree with you, NEVER through the airport with bare feet. I’ve worn socks thru security and then took them off.

    • Jennifer
      March 20, 2016 / 3:03 pm

      I’ve done that too! Then washed them in my hotel sink before rewearing going home!

    • Jennifer
      March 20, 2016 / 3:03 pm

      My wrap went over my legs this trip! It’s nice to use as a makeshift pillow too:)

  26. March 20, 2016 / 10:56 am

    You always hit that style sweet spot Jennifer! Enjoy your holiday…I have a friend whose husband is an architect and he was involved in designing a residential area of Loreto Bay. I hear it is gorgeous…they live there for many months each year.

    • Jennifer
      March 20, 2016 / 3:05 pm

      Thanks Leslie! So do you my friend. It’s so pretty here. The little homes are fabulous. Great weather. Sunny and hot!

  27. March 20, 2016 / 10:12 am

    Where do you put the hat when you get on the plane?

    • Jennifer
      March 20, 2016 / 10:41 am

      I put it upside down under the seat in front of me. It’s very flexible synthetic straw. The brim rolls under slightly while there, and strengthens easily. You couldn’t do that with traditional, stiff straw. It would crack.

  28. Ann Hall
    March 20, 2016 / 10:08 am

    My Daughter and I were upgraded on a flight to Australia. I am from the generation where you got dressed up to travel on an aeroplane and my daughter is very glamorous It was wonderful, the food and the luxurious seating were amazing. So much so we wondered whether we could get our return flight upgraded too. We went to the Emirates office in Sydney to enquire. Needless to say we flew back economy.

    • Jennifer
      March 20, 2016 / 10:44 am

      I’m from that era too Ann. We didn’t have much money growing up, so travel was a very special event. The upgraded food and wine is pretty special:)

  29. March 20, 2016 / 10:07 am

    Never been fortunate enough to get a flight upgrade – good tips to follow and will give it a go. Wish us luck.

  30. March 20, 2016 / 8:41 am

    Great travel outfit! Comfortable can be stylish! And I like your hat tip!

    I also always bring a wrap or big scarf on the airplane, and it has saved me many times…

    It’s funny, I ALWAYS think about the possibility of being upgraded when I dress for a trip! But I have never been upgraded. So many trips in the last 25 years have been with a small child, and I blame them! 🙂 But I have also traveled by myself quite a bit…

    I hope you are having a fantastic time in Mexico!

    • Jennifer
      March 20, 2016 / 9:11 am

      Thanks Andrea. I did my fair share of traveling when my kids were little. Not surprisingly I was never upgraded with them in tow!

  31. Jim
    March 20, 2016 / 8:39 am

    And for the man ? In your travels??

    • Jennifer
      March 20, 2016 / 9:15 am

      The same things apply for men. Sweats and sloppy clothes won’t get him treated as well as a man wearing chinos or clean jeans and a collared polo shirt.

  32. March 20, 2016 / 7:46 am

    I always dress nicely in something comfortable and smart when I’m flying…. and I’ve never, ever been upgraded. I must be on all the wrong flights. Enjoy your holiday, Jennifer.

    • Jennifer
      March 20, 2016 / 8:18 am

      Thanks Sue. Upgrading is the luck of the draw. I know you always look fab so it’s just a matter of timing:)

  33. Catia
    March 20, 2016 / 7:36 am

    Very stylish outfit and though comfortable. I like your hat. Looking forward to your next blab.

    • Jennifer
      March 20, 2016 / 8:16 am

      Thanks Catia! It’s always fun to chat with Susan and Pam. Glad you’ll be able to join or listen after.

  34. Gail Russ
    March 20, 2016 / 7:09 am

    Fourteen years ago (and where did the time go?) I decided to celebrate my 50th birthday by spending a week in London. Queen Elizabeth’s Golden Jubilee would be in full swing during my stay; in fact, her coronation was on my first birthday, although she become the monarch a year earlier in 1952. When I checked in at the British Air counter, I remarked to the agent while she looked at my passport, that she could see that Her Majesty and I both would be celebrating our Golden Jubilee on June 2. She stepped away for a moment to confer with someone, and came back to tell me I had been upgraded to Business Class for that very long trip. Heaven! The completely reclining seats were fairly new then, and I had the most comfortable transatlantic trip ever. I am sure, however, if I had not been dressed well, I would not have been upgraded. It is entirely possible to be comfortable and presentable at the same time. Thanks for reminding us!

    • Jennifer
      March 20, 2016 / 8:11 am

      Lucky you Gail! I’ve never been upgraded for a transatlantic flight. That’s fantastic!

  35. Yvonne
    March 20, 2016 / 5:34 am

    Great travel outfit and I love the big white shirt!
    So true – you never know who you’ll see in an airport. So many times we’ve run into old neighbours, friends and business associates. Last time on the plane, I sat beside a Canadian TV personality.

    • Jennifer
      March 20, 2016 / 8:25 am

      You’re so right Yvonne! I want to look my most comfortable best if I’m flying.

  36. Laney standel
    March 20, 2016 / 4:43 am

    As a retired airline employee I can tell you I was always amazed, saddened and left shaking my head and rolling my eyes as to how people dressed…..not merely for airline travel, but to leave their house in broad daylight ?

    • Jennifer
      March 20, 2016 / 8:39 am

      It is sad. I’m sure you’ve seen it all Laney! For me, it’s self respect. Thanks for reading.

  37. March 20, 2016 / 3:16 am

    I had not thought about the thin legged pant issue, but you are right and I will wear socks to the airport from now on! You look lovely as always…have a wonderful time on your vacation.

    • Jennifer
      March 20, 2016 / 8:38 am

      Thanks Pam! I was always reminded about the pants in the lavatory! Now it’s entrenched in my brain 🙂

  38. nancy
    March 20, 2016 / 12:57 am

    Have a Fantastic Holiday!

  39. Ann Kelley
    March 19, 2016 / 11:03 pm

    I am sorry, but this looks like a gardening outfit to me.

    • Jennifer
      March 20, 2016 / 8:35 am

      That’s funny Ann. I sort of agree about the hat because of its size. But it’s the only way I could get it to Mexico with me. You must be a neater gardener than I am. I end up crawling in the dirt on hands and knees if I garden. So open sandals, white blouse and my newest pants wouldn’t be what I wore. Thanks for reading.

  40. Elizabeth Tierney
    March 19, 2016 / 9:30 pm

    I LOVE that hat!!

    • Jennifer
      March 20, 2016 / 8:37 am

      Thanks. It’s from Coolibar Elizabeth. Very reasonably priced!

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