Early Morning Flight: What I Wore

Early Morning Flight: What I Wore

Travel is always tiring but yesterday was more exhausting than usual. I’d raced around the day before so didn’t finish packing until midnight. I got to bed in time to get four hours sleep but my mind was buzzing and it took a long time to fall asleep. Then my eyes popped open before the alarm went off so I ended up getting three hours sleep. Then my morning went south and I dragged all day.

I never want to risk being told my bag is too big to carry on a flight so I took your advice in this post and switched the new one I’d bought for this smaller one. Lost luggage is a nightmare. Been there done that.

My new suitcase stands as tall as my old one but the size is different. The wheels on my old suitcase accounted for 1 1/2” of the bag height. The spinner wheels on my new suitcase account for 4” of the total height. That means I’ve lost a lot of suitcase capacity!

Jennifer Connolly of A Well Styled Life wearing straw hat, denim jacket and Eileen Fisher pants

staw hat –  tank top –  –denim jacketpantssneakerssuitcase

I got a rude shock just as our cab pulled up. I’d laid my clothes out the night before and planned to wear my favorite travel pants, suede ballet flats, a simple tank, and a blazer. But that’s not what I wore because I couldn’t close my suitcase. I kneeled on it then sat on it but there was no chance of it zipping. That’s when I realized I needed to wear my bulkiest shoes so my suitcase would zip.

I’ve never traveled wearing sneakers. I prefer to dress less casually when I travel because I think we get better treatment when we look better. All of a sudden my blazer looked wrong so I switched it for a denim jacket.

I was traveling wearing my new non-crushable straw hat… which meant I would have hat hair. This all felt too casual for my comfort level so I switched to a pearl necklace which added the polish I needed.Rare Objects book and straw hat on flight

I felt appropriately dressed but wondered, what happened to dressing nicely to travel? My denim jacket and sneakers ended up looking pretty dressy because there were more people wearing flip flops and shorts than I care to remember.

I need to re-evaluate my personal item carry on before we leave for our next trip. Having your luggage lost as you embark on a cruise can have nasty results.

What do you wear to travel?

Thanks for reading and have a great day.



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


  1. Lori
    March 11, 2019 / 2:53 pm

    I like going to see new places, but I really hate getting there. I try to never check a bag, just because I can’t stand waiting for the carousel and because I have a fear of my stuff getting lost. I can usually pack everything I need for a three week trip in my carry on and my under seat “personal item” bag. The challenge for me is my cosmetics. All of my necessary items seem to keep expanding lately! I am experimenting at home with whittling down all that stuff. Perhaps I should just buy it when I get to my destination instead, but I just hate to throw away travel sized things that still have a lot of product in them. As for the travel outfit, it is usually EF crepe pants, a tee, lightweight jacket and slip on shoes(with compression socks) The carry-on always has jewelry, toiletries, reading material snacks and sunglasses and a large scarf that can be used as a blanket. Getting enough sleep before a trip seems impossible, so I try to sleep on the plane.

    • March 11, 2019 / 11:27 pm

      I wish I could sleep on a plane but I’m too buzzed. Just like the night before we leave.

  2. Kay
    March 11, 2019 / 12:39 pm

    You look more pulled together and dressed than 80% of the women I see on any typical flight, so don’t stress. I travel a lot, and I almost have it down to a science (almost, LOL). With a new suitcase, I would pack it first before the trip just to see what it would hold. I have everything I take with me (aside from shoes and clothes) in small zip bags. I pack the ones I will need for the trip (toiletries, make-up, first-aid, etc.) I don’t always take every little “kit.” I have one for laundry, but I wouldn’t need it for some trips. I also have a small “dining” kit that would fall into the same category. Clothes go into packing cubes and shoes into plastic grocery bags. Jewelry, medications, phone charger, etc. go in my carry-on bag. I pack small, but I always check the bag. There is no way, due to physical limitation, that I could lift a bag into an overhead bin, and I’d probably bonk some poor soul on the head taking it down. I factor time for checking the bag and picking it up from the carousel into my time budget. I don’t wear jewelry on the plane to cut down on security hassles. I often travel alone, so I don’t have my husband or anyone else to help me wrangle my luggage. Travelling by plane is stressful enough that any added hassle is just not worth the trouble.

    • March 11, 2019 / 11:29 pm

      I’m very curious about travel cubes. I may try them this summer for our trip overseas.

  3. Jude
    March 11, 2019 / 11:22 am

    Traveling is stressful….period.
    Your outfit looks nice but first the hat. Even with precheck, you have to take it off, jacket too and probably the necklace because of metal. I travel for months at a time and always check a bag. It is free with my credit card. I am thankful I have never lost it. I weigh it on my home scale the night before. I don’t overpack as I may shop.
    I carry some makeup, underwear, medications, change of clothes, toothbrush and sometimes a coat depending on the destination. I also take bleach wipes for trays, seatbelts and touchscreens.
    I cannot stand people having large carry ons or backpacks that bang into other people. ..my stuff fits in and under the seat for easy access unless I am in an exit row, which is often the case.. I never wear jewelry when traveling. Simple earrings…. Even the cheap jewelry can make you a target in some places. Hats are in the carry on. Shoes must be slip on and always socks. Even with precheck, you have to make it through smoothly…taking off all kinds of stuff is a hassle and slows everyone down.
    I love jeans but on trips, I wear pull on pants EF
    A t-shirt, and a cradigan…I take a blanket in case of chill. Don’t ever walk around an airport or plane with no shoes and socks.
    This is what will do as I head to NZ and Australia for a month very soon. Turning 60 in Sydney.
    Just my way….BTW you look adorable.

    • March 11, 2019 / 11:34 pm

      Thank you. I have a Nexus card which gets me TSA pre check so I can leave my shoes, jacket and hat on. It’s almosr civilized. My personal item fits under my seat so long as I’m not in an isle seat. Isle seays stink these days because everyone slaps you in the face with their bag as they pass you in the isle.

  4. Chris
    March 10, 2019 / 6:02 pm

    I haven’t traveled with heavy sneakers in years. They don’t look stylish compared with the many slip on styles that work equally well for long walks. I just returned from a weeklong trip to Florida wearing comfy cropped jeans, a white tee and a blue/white patterned Tommy Bahama short jacket. Slip on Eccos. Very comfortable and more stylish than 90 percent of the women on my flight. I also chose my other shoes based on weight — Croc sandals from Walmart for the beach and silver Bernie Mac wedge sandals that go with everything. Minimal lightweight costume jewelry. I got by with a 21 inch Delsey suitcase, which I checked through, and a wheeled under seat carryon. I also had an extra zippered tote in case I needed more space for purchases on way home. I didn’t. Best packing strategy ever. The bar is pretty low for topping the style of your fellow passengers, I’m sort to say.

    • mrsben
      July 27, 2019 / 7:43 am

      I travel very similar to Chris as most of my destinations target warm or tropical weather to escape the winter (as I live in Canada). That said; instead of a tote I use a stylish leather backpack that slips easily under the seat, stashed with essentials (a small cross body bag/medications etc.) and also use on sightseeing//shopping excursions which usually includes a pair of different footwear , so I can interchange if need be for anatomy relief (namely back, legs, feet). I also check one small piece of luggage which though old, I love because it is soft sided and is expandable ‘n lightweight plus has wheels and a handle making it easy to navigate. Last but not least, I feel you looked very chic and for what it is worth … ☺ ….. feel that your travel ensemble was very appropriate.

  5. Gayle
    March 10, 2019 / 4:57 pm

    Now how do I choose a bag with wheels that do not use up packing space? I hope my
    Sales person knows about storage space!

  6. Carol
    March 10, 2019 / 2:16 pm

    I think what you wear when you travel depends on the type of travel you are doing. In my case, hiking is almost always involved. I travel with hiking poles so I have to check my suitcase. To free up space I usually wear my hiking boots on the plane. Not the best fashion statement, but practical. I take clothing that can be hand washed and that will hang dry quickly. I take along a couple of scarves that dress up simple tops for dinners out. I might take along a necklace or two, but only ones that I don’t worry about not coming home with. Besides hiking pants (which I also often wear on the plane – lots of pockets) I take a pair of basic black light weight pants. If I am going to a cool climate I pack a pair of long underwear which I can also sleep in if necessary. I use my backpack for my carry on. I always take a rain jacket with a hood, and maybe a fleece depending on the climate. My most difficult thing to pack is cosmetics, but I do my best to keep them at a minimum.

  7. Yvonne
    March 10, 2019 / 2:15 pm

    I don’t travel light and if all I could take was a carry-on, I wouldn’t travel at all LOL! I always seem to have direct flights whenever I travel (the advantage of living in Canada’s largest city) so I’ve never had any luggage lost. I dress for style, comfort and in layers for most flights and especially when travelling in the winter to a warmer climate.

  8. Barbara
    March 10, 2019 / 1:59 pm

    You need the Away larger carryon bag!! They are great! And you can charge your phone and stuff!

  9. Donna A Curley-Izzo
    March 10, 2019 / 12:25 pm

    Thank you so much for being real, Jennifer. It is reassuring and validating to know that all of us get off schedule and are tired and harried from time to time despite our best intentions. BTW, you look great for having had three hours sleep and a wrestling match with a suitcase.

    • March 11, 2019 / 11:24 pm

      I’m happy to be real Donna. Sharing white washed versions of real life is depressing for everyone.

  10. Susan Gowan
    March 10, 2019 / 12:16 pm

    We went to Ireland last fall and over the years I have trued to pare down what I take. Our carrier allowed us to take one checked bag between my hubby and me. I took a backpack wheeled carry on and always take a generous-sized purse to carry essentials: some jewellery (always inexpensive), some reading material and a book of crosswords, toothbrush and paste, my meds.On board the flight I choose to be comfortable and warm above all: pair of jeans or leggings, a long tee shirt , comfy socks and sneakers with a three season jacket. The carry on contains essentials: two or three complete outfits and lingerie / pajamas in case my luggage is lost. Happened on my first ever flight to Amsterdam so I am always anxious.

    • March 11, 2019 / 11:22 pm

      I’ve had mine lost too so I’m always careful

  11. March 10, 2019 / 12:10 pm

    I wore my gel-bed Adidas sneakers when we traveled to Grand Cayman last month because they were the bulkiest pair of shoes. Lol. I wore skinny jeans and a sweatshirt/sweater – also my bulkiest items since we were going to a warm climate. I’m usually like you and tend to dress up a bit, butI have to say,I felt like I fit right in to the majority of travelers, and my feet were oh so comfy????.

    • March 11, 2019 / 11:20 pm

      I’m right with you Cyndi.

  12. Wendy Dunbar
    March 10, 2019 / 11:49 am

    I love your crossbody bag with the white piping! Where did you find it? I agree that the hat and the necklace made this outfit!

  13. March 10, 2019 / 11:17 am

    I think the necklace made the outfit. Well, that and the hat. But I’m with you. I have to find a new bag. My old one broke! So searching!

  14. Mary
    March 10, 2019 / 11:11 am

    Thanks to all of you who check bags so I don’t have to????. I use an old london fog wheeled bag that fits the onboard size requirements along with a large purse that zips and fits under the seat in front of me. Last October 1 week in Paris had room to spare in my luggage. On flight I wore comfy dark jeans, long sleeve solid color tee (black, navy or medium blue), ecco leather sporty shoes for running though ORD and CDG, big scarf and trench. This is my travel outfit for spring and fall. Adjust for winter and summer. Enjoy Mexico.

  15. Susan
    March 10, 2019 / 9:31 am

    Even though I travel with a European size carryon I usually check it. Never had a bag lost for more than a day, and as a carryon I always take a nice leather backpack. It always has a couple of shirts,undies, meds, contacts, phone, charger, in flight toiletries and makeup in small travel sizes. ( I pack foundation in a contact lens case, and hair gel and stuff too. It’s plenty for a week or 10 days.) I wear black ponte pants and a 3/4 sleeve t-shirt in a color that goes with the rest of my clothes. Then add a nice scarf and usually a quilted lightweight jacket from LL Bean. ( travel to Europe a lot in the fall.) Never take nice jewelry, only costume stuff. Always wear something that I can wash out and wear again. Occasionally I wear my sweater dress on the plane with tights and slip on sneakers, plus scarf and jacket. I only wear slip on sneakers on the plane-Ecco has nice ones. So much easier…

    • March 11, 2019 / 10:44 pm

      I love Ecco shoes. I completely agree that slipons are best.

  16. Joanna
    March 10, 2019 / 9:26 am

    I always check a bag. My pet peeve is all those trying to squeeze their luggage in the overhead bins. On my last flight home, the flight attendant took our winter coats down to accommodate others suitcases. I told him we had none and we did not want to sit on a five hour flight holding bulky jackets. He then found s spot to Stuff them in.
    I’ve only once had my luggage not arrive with me. It was delivered the next morning to my hotel. It caused me no hardship as I travel with a soft, carame coloured backpack with necessities.
    It seems to be a trend to pack what you need in a tiny little suitcase to avoid paying a small fee or the slight possibility of it going astray. To me, it’s not worth the hassle of trudging through airports dragging a suitcase. To pack so few clothes as to have to wash things in your sink at night (friend) and not have variety.
    But, that’s me,

  17. Amy
    March 10, 2019 / 8:23 am

    HI Jennifer, I travel a lot for work and as often as I can personally. I don’t know your suitcase brand, but i won’t consider any brand other than TravelPro. These suitcases are amazing and if you look at many flight crews, you’ll see they carry them. They are so lightweight, and my hubby and I own both the carry on size and the larger size. I OFTEN check a bag. I find it so annoying that people can’t be separated from their stuff, in my many many flights, my bag was only delayed by one day one single time. Anyway, to each his own, i just don’t like hoofing around the airport with so much stuff. Traveling internationally is even harder with any kind of large bulky bag regardless of how your travel when you arrive. What I wear: cooler times/climate: ankle boots, long sleeve breathable t or white shirt and another layer (cardigan, vest, nice sweatshirt i have two from SOMA and J Jill that are so nice i can switch them as a jacket later). Warm weather flight: sneakers, short sleeve breathable shirt, denim jacket or duster. These pieces are all so mix and matchable. I’m done with over packing anymore, it’s just too exhausting. I bring about 3 scarves, and a number of not too expensive jewelry pieces (as mentioned above they can be lost or stolen). I hope you’re caught up on sleep and enjoying vacay by now! My hubby and I leave next Saturday for personal travel…..yeah!!!

    • March 11, 2019 / 10:40 pm

      Checking into TravelPro because this new bag isn’t cutting it. Have a great trip

  18. Cathy
    March 10, 2019 / 8:20 am

    I never sleep well before a trip. And with all my years of corporate travel I have yet to be a good packer. I’ve watch millions of video, I plan, I have cubes, but I always have a overloaded suitcase.

  19. Susan
    March 10, 2019 / 8:19 am

    My travel uniform is black ponte pants (dressier than leggings), a medium gray heathered v-neck tee, a dark gray heathered lightweight swing cardigan, and my black Geox sneakers. I always add a nice infinity scarf. The outfit looks polished, yet it’s as comfortable as pajamas! I can’t imagine wearing jeans on a overnight flight. My secret: I wear the buttonless cardigan backwards when I sleep! It keeps me warm, doesn’t fall down like a blanket, and when I’m seated, it looks just like a high-necked long sleeve top. I’m reluctant to switch to a hard-sided suitcase. I can always cram one more thing into my soft-sided TravelPro.

    • Lizette
      March 11, 2019 / 7:30 am

      Great tip about wearing your sweater like a blanket!

    • March 11, 2019 / 10:38 pm

      Love this idea!
      Looking Inyo a TravelPro now.

  20. March 10, 2019 / 8:04 am

    I always travel in some type of black pull-on pants (usually EF) for comfort and a classier look, and then layer on top based on my destination. When I arrive, I hang up my travel outfit till it’s time to fly back. If I am traveling from cold to warmer I make sure I am able to remove the top layer, usually a jacket or cardigan, when I land and have my sunglasses at the ready. I have never lost a bag, so I always check my larger bag. I don’t like competing for space in the overhea or lugging my bag to my seat, and I can be more relaxed with what I pack. American Express likes my approach since I find the annual fee pays for itself with free checked bags a few times each year. Some other things I do to reduce last-minute stress: make sure my bag closes the night before I leave, have my travel outfit set out and book flights that leave mid- to late-morning. I hope you bounce back nicely with a good night’s sleep and have a wonderful time!

    • March 11, 2019 / 10:37 pm

      Thanks Deanne. Lesson to self, pay attention when hubby is booking the flight.

  21. Sandy
    March 10, 2019 / 7:50 am

    All these suggestions of travel outfits are excellent! My comment would be concerning jewelry. I lost a valuable diamond bracelet when traveling several years ago so I wear only minimal inexpensive pieces when I’m traveling. Footwear? I wear shoes that slip on to make walking through security a breeze. I have on socks and then slip them off once I’m through security and stash them in a suitcase pocket to be washed and bleached later…or cheap socks to throw away.

    • March 11, 2019 / 10:35 pm

      I leave all my real jewelry in a safe deposit box at home. Costume jewelry only to travel. I don’t want to worry about it.

  22. Laurel
    March 10, 2019 / 7:33 am

    You appear to have the same pre-travel sleep patterns I do! Try as I might, I just don’t sleep well before flying – nervous about missing the plane, the drive to the airport, what did I forget, etc. I tend to fly in EF separates (pants, tee or tank, a great longer knit jacket I’ve had for years) and add a scarf for color and warmth. I need to wear compression socks, so I usually wear dark metallic sneakers or comfy oxfords. But comfort and warmth are my first priorities.

    This year we’re going hiking, and I don’t want to wear hiking boots on a plane…not to mention how clunky they are for walking indoors. And we have trekking poles which can’t be in carry-on luggage. 🙁 So I guess we’re checking our bags, which I haven’t done in years.

    • March 11, 2019 / 10:33 pm

      Good luck. Hiking sounds fun!

  23. March 10, 2019 / 7:32 am

    While I’ve always packed light… one checked bag for my husband and I together, we’re now preparing for our first carry-on only trip… three and a half weeks in Europe! I always wear sneakers when I’m travelling because I find them comfortable and they’re the bulkiest shoes I take with me. My style at home and away is dressy casual.

  24. Linda
    March 10, 2019 / 7:29 am

    I hope you have a wonderful trip! I myself am in the middle of a trip.

    I wear mostly soft, lightweight cottons head to foot for my travel with either a lightweight shirt, neutral colored trench and my athletic shoes. Having not flown in years, I have not needed to upgrade my suitcase but should I fly in the future, I will pay close attention to what I pack my stuff in.

    • March 11, 2019 / 10:32 pm

      They’re getting increasingly tough about the size of carryons.

  25. Sherrye
    March 10, 2019 / 7:23 am

    I have not officially checked a bag for years while traveling. I carry on a bag that is probably right on the edge in size. I have had to check it at the door as boarding if there is limited luggage space, but that means it’s among the last bags loaded & first unloaded. My travel outfit is comfy but casual stylish. I usually do a long sleeved layer because I get chilled in flight.

    • March 11, 2019 / 10:31 pm

      I may need to get a slightly larger bag and plan for them to gate check it. I do feel safer doing that.

  26. March 10, 2019 / 6:41 am

    What a nerve wracking morning that was!! That carry on suitcase looks SO small. Hopefully your tote will make up the difference and you will be looking your usual lovely stylish self for the remainder of your trip enjoying the warmth and fun you signed up for. Bon Voyage!

  27. Bonnie Hall
    March 10, 2019 / 6:34 am

    Ohhh, I feel your pain about lack of sleep before a big trip! I simply must check a bag and (fingers crossed) so far have never lost a bag. I do carry a change of underwear and fresh top along with basic toiletries and whatever outerwear might be required in an “under the seat” carry-on just in case. The nice thing about most of our travels being in a motorcoach is the motorcoach is like a huge suitcase. Have a relaxing cruise!!!

    • March 11, 2019 / 10:29 pm

      Thank you. I can’t wait.

  28. Kathy
    March 10, 2019 / 6:30 am

    I also like to look nice when I travel. However, I like to travel with only a carry-on so sometimes that means wearing sneakers on the plane! I like to wear my Vince leather slip-ons, jeans and a sweater or t shirt depending on the season. I’ll add a denim jacket or utility jacket.

    • March 11, 2019 / 10:28 pm

      We think very much alike.

  29. Eileen
    March 10, 2019 / 6:28 am

    To cool climates I wear ankle boots, jeans, shirt, sweater, trench with liner, scarf. To warm climates I wear sneakers, jeans, shirt, and a version of a safari cotton jacket, cotton scarf. I always take and usually wear in the plane, a light pack able down jacket. I grew up near foggy San Francisco, so I always have a down jacket close by.

  30. kate trim
    March 10, 2019 / 5:56 am

    I always like to look put together. I agree that occasionally you get better service. Unless it’s a very short cruise I couldn’t imagine just taking carry on! I usually pack small hand luggage with medicines, valuables and a change of underwear and a clean top and a couple of scarves in case my luggage is delayed. Even cruising your luggage usually catches up with you if it gets lost.

    • March 11, 2019 / 10:27 pm

      I’m rethinking my entire cruise wardrobe. I hate to look boring but I don’t want to check a bag.

  31. Shirley Riley
    March 10, 2019 / 5:19 am

    I looked at the link for your straw hat, but I did not see that it was non-crushable . Please explain.

    • March 10, 2019 / 10:11 am

      It’s an inexpensive, real straw hat, not synthetic. If it got crushed or folded the straw would crack. I did pack several synthetic straw hats in my back and they popped back to normal after being crushed in my bag all day.

  32. Shari
    March 10, 2019 / 5:09 am

    I’ve traveked sooo much and always it is a packing challenge! Oh, i love the new bag! I’m shopping for new luggage now…not an easy task!
    Spend a lot? Does that equal quality? Hmmm???
    I travel in the same stretchy tan pants aand a leopard tunic with a black jeans jacket….it is seasonless and each part can recombine with other items later. When I wear it other times we ask…”where is she going” lol!
    Last year we were away 3 months! I sure got tired of the clothes and even bought a couple of tops… ut sticking to basics gets you through almost any occasion . Old Navy has some great basic travel tunic and dresses!
    Wish MY. Rather lived in Mexico! Have fun!

    • Shari
      March 10, 2019 / 5:10 am


      • March 11, 2019 / 10:26 pm

        Lol!! Spellcheck is a nightmare. It’s all good! Xx

  33. Holly
    March 10, 2019 / 4:46 am

    Happy Sunday….. I love to fly and I too like to look my best! I try to dress up a little when I fly (especially when flying in first class) but still want to look nice otherwise. I try not to wear heels as my feet start hurting me walking all over the airports. Yes your necklace to make that added touch of class you needed.


  34. March 10, 2019 / 4:44 am

    Like you ain’t believe in being comfy, yet smart looking. Ballet flats with leggings or similar, tee shirt,dark blazer or white jean jacket etc. Depend on where Im headed.
    Have a wonderful time!

    • March 10, 2019 / 5:05 am

      This should read I not “ain’t”….I hate this tablet for changing much of what I type!!
      Ain’t? Not me…..

    • March 11, 2019 / 10:24 pm

      Lol! I can’t believe how my comments get spell checked. I often go back and cringe at what got printed.

  35. Barbara
    March 10, 2019 / 3:51 am

    I have just travelled to Egypt (very long flight) and chose to wear black pull on pants from Chicos, a long sleeve powder blue dressy knit tee shirt with a no button cardigan longer length from Athleta ( Christmas gift) and black driving moccasins ( very comfy)
    I was comfortable and felt I looked casual but not too dressy.
    Oh with silver simple jewelry.

    • March 11, 2019 / 10:08 pm

      That sounds perfect! I’ve always wanted to visit Egypt. Lucky you.

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