What to Wear to the Airport/When Traveling

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Back in the day, traveling used to be a special occasion that people dressed up for. These days, anything goes! When you’re waiting at the airport, maybe at a TSA line, you’ll see a lot of people wear everything from maybe a regular business suit all the way to a hoodie with sweatpants.

Alex Pettyfer in gray sweatpants and shirt
Alex Pettyfer shows you what NOT to wear to the airport if you want to look classy

What Should You Wear To The Airport & Why Should You Do It?

Obviously, dirty sneakers, shirts with holes, and sweatpants are acceptable and if that’s what you want to wear, go for it, however, I like to say luck favors the prepared and if you’re dressed up at the airport, it can still have a number of advantages.

Sven Raphael's go-to suit when travelling
Sven Raphael’s go-to suit when travelling

Clothes Send Powerful Signals To Others

Let me start with a story. A few years back, I was on a plane, our business was much smaller and we wanted to extend our credit line. I was dressed well and the guy next to started a conversation and it turned out, he was a manager for my local bank. So when I told him what our plan was and had a hard time getting more credit, he was like “Well, wait a second” and he gave me his email address, I followed up with him and I got an increase for my credit line. My banker was so impressed that he called me for the first time ever and wanted to get together with me for a coffee and he was like “By the way, how did you get your credit line increased?”. So the only reason that whole thing started was because I was well-dressed and trustworthy. If I would have worn a t-shirt with ice cream stains, I probably would have not gotten that offer from the gentleman.

Now the easy thing is because everyone else is so dressed down, you can just get a rather casual ensemble that makes you immediately stand out from the crowd.

Sven Raphael's Samsonite polycarbonate luggages
Sven Raphael’s Samsonite polycarbonate luggages

Your Luggage May Get Lost

The other reason you want to dress up when you fly is that your luggage can get lost. That happened to me just last year on the way to my best friend’s wedding where I was the best man. If I had not worn a nice pair of pants that would actually fit me, I would not have been able to attend that wedding without looking like a complete douchebag.

Specific Pieces You Can Wear When Traveling

I would say find a compromise between comfort, functionality, and stylishness.

Sven Raphael's ideal travel jacket
Sven Raphael’s ideal travel jacket

A Comfy Jacket

I always wear a jacket when I travel because I can easily take it off, maybe use it as a blanket, or just have an additional layer to keep me warm because you never know how hot or cold it’s going to be on a plane. I like a very unstructured jacket that is extremely comfortable, no shoulder padding at all, and something that you can just throw into the corner that doesn’t wrinkle easily. Ideally, it has enough pockets because between your passport, your phone, your tickets, and other stuff that you need, you want to have enough storage space.

Green Safari Jacket
Green Safari Jacket

 

During the warmer months of the year, I often travel in my Safari jacket which has really big pockets, it’s a nice casual jacket and it just is perfect for traveling because of that. Ideally, you want a jacket that is dark so it doesn’t pick up stains or something with a pattern. Alternatively, I think a navy blazer in a soft material such as cashmere, a cashmere wool blend is ideal.

OCBD Oxford Cloth Button Down Shirt by Brooks Brothers
OCBD Oxford Cloth Button Down Shirt by Brooks Brothers

OCBD Shirt

I try to go with a dress shirt, in this case, I am wearing a button-down collar shirt because it doesn’t require a necktie and it is made out of a fabric that is very hard-wearing. You definitely always want long sleeves but avoid French cuffs because the metal may set off the metal detector, you may have to go through stuff again and it’s just annoying. Another really great option for air travel is a long sleeve polo shirt, specifically, a white one.

Travel-Friendly Accessories

Now if I go on a longer trip, I always either wear a tie because my luggage can get lost or I try to wear a bow tie or keep one in my pocket because that can be a lifesaver if I need to go to a more formal occasion later on. I always travel with a pocket square but I skipped the boutonniere because when I fold a jacket and put it somewhere, the flower would likely be squished, however, the pocket square instantly upgrades my outfit and makes me stand out from the rest on the plane. In an ideal world, you skip the belt as well as suspenders and just go with side adjusters, however, that doesn’t always work and so a belt that comes off easily is the best way to go.

If you’re on really long flights, I suggest you invest in a pair of over the calf compression socks because it compresses your veins and makes sure the blood keeps flowing and you don’t end up with a blood clot that might be lethal. That’s especially true if you’re an older gentleman; if you’re younger and you don’t worry about it, I still suggest wearing some nice over the calf socks.

If you’re a watch guy, of course, you want to get a wristwatch. Personally, I try to bring it along in my luggage because I don’t want to take it off, put it back on, it’s just one more step when going through security and I simply try to avoid it. Of course, to me, time is money so I invested in TSA Pre and so I waste as little time as possible waiting at the airport.

Gucci Horsebit Loafer 1953
Gucci Horsebit Loafer 1953

Slip-On Leather Shoes

In terms of shoes, of course, I go with leather that matches the belt but in the airport travel case, I usually opt for a loafer. It could either be a penny loafer it could be a Gucci loafer. Alternatively, you can also go with a monk strap shoe but opt for something that comes off easily and quickly so no lace derbys or oxfords.\

Classic Haggar Khaki Pants
Classic Haggar Khaki Pants

Lightweight Pair Of Pants

For pants, I like something that is easily washable so usually, I don’t opt for wool dress pants instead, I go with cotton chinos and khaki because they are very neutral, can be combined with a lot, and they can be easily washed if I stain them along the way. Alternatively, during the warmer months of the year, I really like seersucker because it’s very lightweight, it’s comfortable to travel in yet it doesn’t wrinkle very easily and always looks neat.

Sven Raphael Schneider wearing a seersucker suit
Sven Raphael Schneider wearing a seersucker suit

 

In terms of a carry-on, I usually bring a computer bag which also contains my camera and all the stuff I need and if I don’t check luggage, I bring a carry-on with really good wheels that is stable enough so I can put my bag on top of it and just maneuver the airport and the cities I am in very easily.

What do you usually wear to the airport? Share with us your travel tips & tricks in the comments below!

Reader Comments

  1. Most needed article! Too many wardrobes by Walmart on transportation these days. Look to the 30’s travel posters for the way it was and still should be. Let’s give the TSA morons some quality material to rub their unmanicured hands in.

  2. When travelling, I tend towards a sport jacket ( a blazer would work ), chinos, dress shirt, and tie. My belt, watch, reading glasses, or any other objects that would set off the metal detectors go in my carry-on. Shoes don’t have to be loafers, as long as the are easy to get on and off. If I am travelling during colder weather, either from my departure point or my destination, I also wear a light wool sweater. If one gets cold easily, especially when flying, a sweater is a good idea anyway. I leave my wallet and passport ( if I have my passport with me ) in my jacket, in a buttonable pocket. The jacket goes in the tray with my carry on and shoes. Also, keep an empty water bottle in your carry-on; you can fill it once you are past security and you’ll have water on the plane.

  3. Sven:
    Good job!
    I particularly like the white long sleeve polo shirt idea.
    Tommy F must have on the wrong side of the bed today!
    Regards

  4. I agree entirely with Raphael. In addition, I always carry in my hand luggage a spare set of underwear, socks, t-shirt, trousers, a shirt and a small toiletries set. My luggage has been lost many times, once when I was in New York, my bags arrived over a week later. So it is nice to have something clean to wear before having to run to the shops to buy whatever is needed until one’s luggage turns up!

  5. Great suggestions. When I was a kid in the 70s, people still dressed up for airline travel. When I was flying several times a year during college in the 80s, it was already starting to get more casual. I always wore a soft, comfortable suit and tie. I’d politely ask at the gate whether an upgrade to first class was available. I was probably upgraded for free one time in three, and was never carded when I got my complimentary drinks. That wouldn’t have happened if I was in jeans. Of course that sort of thing could never happen today–I have to pay for my first-class tickets now.

  6. For long trips (especially international), I always check one bag and carry on a small bag with enough essentials to get me through 2-3 days. My luggage was lost on a week long trip to Moscow a few years back and I didn’t receive it back until the day before I flew home. Though Moscow has some fantastic menswear stores, I was very glad to have my emergency carry-on wardrobe and enough to squeak by. I always wear a navy blazer and jeans when flying and pack 2 pairs of pants and several dress shirts plus underwear and socks plus a scaled down toiletry selection. The extra insurance gives me peace of mind and one less thing to stress about!

      1. English is my first language, Sven (Raphael), and your facility with English is just fine; in fact it bests that of most native speakers . . .

        By the way, I love the shadow stripe socks; I have seven or eight pairs now (and pocket squares, too). I’ve shown your site to my young nephew, who wants to present a good appearance as he enters adulthood. Thanks!

      2. Mr. Raphael,

        Although you say english is not your first language, you should probably avoid nasty slang, such as saying “douchebag” in your presentations. You’re not sending messages between friends but are speaking to an online audience of possibly thousands. You need the services of someone who can really write, instead of the little girl you have writing your presentations who doesn’t know anything, if that is who you’re using. It’s quite immature.
        Another annoyance is when people are relating an anecdote and say either “I was like” or “she was like.” You did this repeatedly. You appear to be smarter than such moron speak, so next time eliminate it if you please, because a gentleman should never try to imitate the current fake President of the USA, or most americans, for that matter.

  7. When I was an international Music Producer with homes in London, Los Angeles and Latvia…(my ex-wife’s birthplace and family origins)…with also investment properties, on beaches, in south-west England and Queensland (both near to international airports, making travel easier), I extensively flew internationally and internally, and often around the North American Continent for my, then, career and also vacations. With various climates, time zones and ‘career aspects’ involving (Southern California to Eastern Europe in March entailed leaving sunny warm sunshine to a two day layover in London, with ‘driving’ rain and freezing winds, to arriving in Latvia’s sub-zero temperatures, still heavily snowing and frozen lakes) important meetings, work commitments to even meetings with government officials in Latvia (regarding international businesses) meticulous planning, especially regarding packing were essential.
    Therefore, I have traveled internationally and internally…America, UK, Eastern Europe and Australia…countless times over many years. I used a variety of Airlines and yet one commonality (almost) always prevailed, especially on international flights. When checking-in, by wearing a ‘quality’ overcoat, sports jacket (minimum requirement!) with tie, shirt and always an upmarket shined pair of shoes, I was frequently ‘pulled-out’ from ‘check-in’ lines (also, a more personal touch with human interaction) and predominantly ‘Upgraded’ in some way, shape of form. Once, when flying ‘British Airways’ (although not always my preferred airline), I showed up ‘dressed-to-impress’ with the full works (Three Piece Suit, Tie, ‘Sharp’ shirt, full-length Bogart Trench with Cornish Tartan scarf, highly shined Brogues) and when taken aside, I was even upgraded from upper-Coach to Full ‘First Class’ and specifically told by the check-in staff, that they “Appreciated how well-dressed” I looked “Doctor”. I had excellent food and service and an even more ‘solid seven hours’ of uninterrupted sleep, arriving into London completely refreshed for a highly successful business meeting.
    This message is not to ‘brag’ or ‘show-off’, but, to inform those out there who disregard such information written (by Sven) regarding looking ‘sharp’ (especially where there may be a chance of a ‘generous upgrade’!!), where, rightly or wrongly, you are observed and ‘judged’ by the airline staff…and a “Gentleman can never be over-dressed when traveling, yet, he can always dress slightly down” if required. As usual…excellent article Sven. Bravo!

  8. My wife and I always wear hopsack navy blazers, non-wrinkle chinos, non-matching shirts and clean/polished loafers….
    We are always treated with respect and frequently complimented by boarding gate agents and crew. They too, deserve to be shown respect and consideration.
    When traveling with our adult children and grandchildren, it is gratifying to see that they always dress appropriately as well.

    1. James,

      A client of mine was one of the original Swinging 60’s stewardesses for Delta. Really cool gal. She kept her flight status active into her 70’s, primarily for the benefits and travel privileges. Back when she started, only the more affluent could afford air travel. Back before Southwest and other cut-rate carriers. She said “passengers then wore their Sunday best, and acted accordingly”. The pre air rage days.

      ( By the time she fully retired, she caught a guy trimming his toenails in the aisle… ) It’s that bad. Don’t get me started on the hoodie-wearing hipster squatters in your [assigned] window seat, then claiming “They were just thinking of YOU because you won’t be inconvenienced when you have to get up to use the bathroom”. Even though they hadn’t laid EYE on you prior to swiping your seat?

      Millenials call these “life hacks”. The rest of us call it unethical or just rude. Even if you pony up for bus. class, you still have to deal w/ riffraff at the terminal, concourse, parking garage etc.

  9. Thank you for an excellent piece on a subject with which I am quite familiar. Having been an airline pilot for the last 28 years, I’ve witnessed the steady decline in the sense of occasion that air travel once had. When flying became cheaper than driving, the clientele changed. The guy in flip-flops with moldy feet that would have been thrown out of an airport when I was a kid, may be sitting next to you for the next four hours in that metal tube tomorrow. The grooming, dress and hygiene habits we see among travelers leave something to be desired….to put it delicately. Someone who takes pride in there appearance will certainly be noticed by the crew.

    Eventually, things will change. Fuel prices will rise and gradually return things to the way they were, and I’m not sure I’ll regret it.
    Keep up the good work.

    1. Steven,

      Given the miles I’ve put in, we’ve probably crossed paths at some point. Thanks for getting us all there safely. Love your optimism for the future, but given I’ll soon be retired military, to be honest, don’t think I’ll be flying commercial again. It’ll be Space-A for the Mrs. & I from here on out.

      Some of the flights [back] from Palm Springs and Las Vegas have been nightmarish. With all the people that can’t seem to budget or manage their finances for a REAL ‘vacation’, 3-day/long weekend junkets are standard. As is using air time for “getting caught up on their sleep”.

      You’re not sharing a plane, you’re sharing a hotel room. No thanks…

  10. Two observations: If you are TSA pre checked, stick with lace ups or a loafer without hardware. I have a few slip ones where the metal buckle will set off a metal detector.

    This is the one time you want to purchase a microfiber dress shirt. Peter Millar has a few nice offerings. The microfiber slides against your jacket fabric with little friction, which is greatly appreciated during frequent position changes while on a long flight

  11. Sven, you touch upon an interesting subject. Unfortunately for us all, as we de-robe and decant belongings into plastic trays, the romance has dwindled. On my last (European) international flight I was the only one travelling wearing a suit and tie. However, departure areas and the planes are all treated as a public lounge. Such are the many indignations suffered I believe few now wish to be dressed well for the pat-down. This, combined with a general lowering of dress standards and formality, results in a resistance and perhaps intransigence to dressing well when traveling.

  12. Wear what makes you look good and demand that TSA do a personal search. I had TSA agent confirm to me that that would overload the system. Maybe they will do away with the whole thing then? TSA is overkill.

  13. Hi Sven,
    What is your advice on packing several suits, jackets, pants, shirts, ties, shoes, etc., for a long business trip? What type of garment bag? Put suits and jackets in individual suit bags and then place in garment bag? Any tips are greatly appreciated!
    ~Paul C.

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