When Traveling Do You Dress For Where You Are Or Where You Are Going?

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When Traveling Do You Dress For Where You Are Or Where You Are Going?

We have all seen it, the guy standing in the middle of the airport wearing a Hawaiian shirt, cargo shorts and flip flops. This in itself isn’t abnormal, until you peek over at the windows which reveals a savage blizzard blaring outside. This guy is someone who dresses for where they are going when they travel. Another woman on that same Hawaii flight is dripping sweat in the back of the Uber because she layered up on the way to the airport. She can’t wait to check in and strip off the layers of clothes at the resort. This woman dresses according to where she is when she travels.

Sometimes people just throw their coat wherever when they travel too.

I Have A Hybrid Method

I have a mixture of the two, as I am sure many of us do, but I do tend to lean towards dressing for where I am going. On my flight to Vegas a few months ago I wore a sweater into the airport and took it off as soon as I was inside and packed it away. I knew Vegas was in the high 70’s, and I usually run a little warm on planes, so I decided to take off what I could while I could.

When I travel during the frigidly cold winter I will often forgo wearing a coat to the airport if going somewhere warmer. Coats can take up a lot of space so I will suck it up during the walk from the parking lot to the terminal to save on packing. That is where my Loungaroo comes in mighty handy.

I don’t go full blown shorts in the middle of winter, or tightly bundled up when leaving a warm weather location and heading home. I think leaving warm and heading to cold is easier to deal with since you can layer up when you land from your luggage.

Final Thoughts

I thought this would be a fun topic to discuss in the comments so it was more for that than anything else. Do you dress for where you are going or for where you are leaving? Or do you do a hybrid set up? And if so which way do you lean?

Let me know in comments!

Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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  1. I have never been warm enough in a plane. So, summer or winter, I first dress for the plane.

    I have a sleeveless travel dress for summer, and I bring leggings with me to put on at the airport. Add comfortable shoes and either no show or short socks and a sweater that’s in my carry on, and I’m good.

    In winter, I switch out the dress for one with long sleeves. My destination clothes are on the top of my packed suitcase, if the climate is different. We most often go to ZIH in winter, leaving MSP in late Jan. So there’s a pair of sandals in the carry on, and I’ve lost the leggings just before landing.

    Once through customs, I go change into a sundress.

    I have a lightweight down jacket that’s for the ride to and from the airport at home. If it’s 5 F, it won’t necessarily keep me warm, but it’ll prevent hypothermia while waiting for a Lyft. It’s squishable enough that I can shove it into a packed suitcase with no problem.

  2. I do the hybrid method but always leggings, pair of flat comfortable shoes, tshirt and ladies cover up or wrap around. I am warm enough to get from the car to the terminal, then can fold up wrap into carry on and I even can pack a pair of soft flip flops in carry on and switch shoes before deplaning. It has worked well but being a woman I think there are plenty of options.

  3. I dress more or less the same no matter where I’m going. t-shirt, comfortable pants for flying (probably sweatpants, though if its a short trip that I’m not packing fight clothes for, jeans are common).

    I’ll usually have a light jacket in carry on (in case the cabin is cold or I want a blanket) regardless of where I’m going (yes even in SE Asia in summer). If I’m arriving into a blizzard, the winter coat will be in checked and pulled out post-baggage claim (but pre-leaving airport). If I’m leaving a blizzard, I’ll probably carry the coat on board the plane with me (doesn’t usually count against carry-on space anyway)

    I guess if it’s delayed, light coat will help me survive the transfer (might opt for a car if it otherwise involves walking, but most cities I do public transit which usually links directly into the airport without too much outside anyway–might grab a cab for the last mile to hotel if it’s not near a station, though I usually rely on transit and pick a well-connected place).

  4. Hybrid method of dress, but I often make my to go outfit of clothes that I no longer like or that are older. I then leave it behind in my destination location.

    • Like Allen Iverson leaving a suit in every city Greg :). It does keep the packing lighter though and I think that is a pretty good idea right there.

  5. I’m with you on foregoing the winter coat if heading somewhere warm from my cold winter home. But I will still wear my baby alpaca wool hat from Peru as I hate having my head cold/ I generally will dress for the airplane, my favorite being a t-shirt, lightweight Under Armour pants, my favorite lightweight jacket in case I get chilly, hat or baseball cap, and athletic shoes. That tends to be a flexible enough set of options. Sometimes depends on what exactly I’m doing upon arrival – rental car, public transport, etc.

    But one time I chose poorly. We were flying home from the Yucatan in February – where it was bitter cold back home. My wife and daughter maintained their shorts and t-shirts. I hadn’t gotten into my above groove at the time and I put on jeans. I figured that although I might be a tad warm for a bit before departure at CUN, it wouldn’t be that bad. Well, guess what? The air handling system inside the terminal was completely broken. No chilled air, no air movement, nothing. (I should have And of course our flight was delayed. People were salty, to put it mildly. I took off my shoes and socks, rolled up my pant legs. I was literally about 10 minutes away from taking my shirt off – not a pretty sight – when they finally began boarding. No, I wasn’t smart enough to just buy a pair of shorts in the terminal either. Overall, I was pretty pissed at myself at the time but it’s funny now looking back!

    • It is amazing how much a hat can make a difference in keeping you warm. And it takes up almost no space which is perfect.

  6. Where I’m going, especially it’s a foreign city after a long flight. I want to be as comfortable as possible in an unfamiliar environment with jetlag.

  7. I’m the guy wearing shorts and a hawaiian shirt in the winter on my way to hawaii. I don’t do flip flops though. I usually bring a long sleeve shirt to throw in my laptop bag in case the airplane is really cold.

  8. I live in a cold climate in the winter and when I go somewhere warm, I wear a longsleeve t-shirt or rugby shirt and a rainjacket to the airport. Though it may be 35 degrees outside, the windproof rainjacket keeps me warm enough. It’s also very light and doesn’t take too much space in my carry on bag (if the plane is cold I just wear it.)


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