Flying Casual Could Be A Costly Mistake: How Sweatpants Are Sabotaging Your Chance At Life-Changing Opportunities

Commercial real estate broker Kyle Matthews is blowing up online for his advice to always dress in a suit when flying, saying that it will open the door to business opportunities. Is he right?

Business tip; Whenever you are flying commercial, especially in business/first class, always wear your best business suit & tie combo (business formal).

When someone walks on the plane in a great suit, white dress shirt & clean tie, I always think to myself, “I wonder what that guy/gal does for a living.” …It is an easy way to network and meet new people, you just have to give a little more effort to dress up and eschew your “I don’t give a sh*t” sweat pants and F-U hoodie.

…Combine the professional clothes with a clean shave, combed hair, and I hate to admit, yes a nice watch helps…

In the U.S., suits are largely only necessary in Washington, D.C. – and even less so now than when I lived there. D.C. is a unique culture that runs on proximity to power, not money, and people aren’t striving to show that they don’t need to dress or are too important to dress. D.C. signals differently.

And watches don’t have the meaning they once did, either. They’re jewelry. You have a smartphone to tell time. I stopped wearing one at the beginning of the pandemic and never picked it up again.

But the basic intuition in this post is right,

  • Dressing well on a plane stands out because most people don’t do it (this is true everywhere)
  • Dressing better than others stands out, you should do this any non-rural place you go except Northern California

I don’t think business attire is how you strike up a conversation. Most people aren’t going to ask you about what you do because you’re dressed well. Smile, say something friendly and welcoming, and see if the other person is interested in chatting if you see value in networking on a plane. There is value in networking on a plane, at least there can be.

  • Airline passengers skew better off than the median American
  • People who fly at what are still business travel times have an elevated likelihood of being business travelers themselves
  • During the Great Recession, British Airways actually ran a promotion to help small business owners fly – and one of the pitches was the people they’d meet on the plane.

The first thing to do is evaluate whether someone is open to chatting. You should be sure your headphones or earbuds are off, and note if theirs are on? The universal sign for leave me alone is headphones in, or worse still putting them in when there’s a lull in the conversation. Leave them be.

But if you’re friendly and open, you might get a chat. The best chats are serendipitous, not cravenly motivated. Just be open and sometimes things just fall into your lap.

Crucially, though, you really do not need to be wearing your “best business suit & tie combo (business formal)” Obviously, look professional and put together but that’s not the same thing as dressing formally.

The real reason to dress in business attire on the plane? You’re heading straight to a meeting, the chance of getting closet space (if your plane still has a closet) is low, and your jacket is going to get creased in the overhead bin. Plus you don’t want to bring an extra bag if you don’t have to. And as an added bonus, your clothing won’t get you kicked off the flight.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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Comments

  1. Of course he is correct . Decent people are neatly dressed and clean and respectful .

    Lately other passengers have been slovenly and/or unclean and disrespectful .

  2. Don’t forget to shitty photoshop and post it on social media. Why is the overhead storage warped behind his head lol.

  3. Hey kyle, I’m flying to Hawaii next month. I’m not going to wear a stupid monkey suit. Keep your advice to yourself.

  4. I’ve solved this issue by wearing a Jets t-shirt on planes. Always a conversation starter no matter where I am in the world (which surprised me) and I can control how far I want to take the discussion with my answers.

  5. Not sure if this is a real thing but I will say this…most people on the plane today look like they’re dressed to mow the lawn.

  6. I have tried that before, wearing a suit, having only a briefcase and no checked bags, and flying between LaGuardia and National.

  7. Not flying to impress anyone. I usually dress casually because I travel to enjoy many vacations throughout the year. I own sweatpants that appear to be slacks only more comfortable. And my shirt is usually quite nice. Since I’m traveling with others I’m not worried about striking up a conversation with others. But if someone does want to have a conversation, I’m open, as long as its not about politics or religion. Happy to talk about why I’m traveling and what new adventure I’m on.

  8. I worked in manufacturing for years. 150-200 flights a year. When I started in the mid 80s I wore suits in the plant. By the 90s I wore casual clothes because it was easier to strike up conversations with shop floor personnel. Those conversations were key to my business success. Id bring a blue blazer to travel. And I was always platinum and in first class. Had great conversations with some big wigs. Some of it brought business to my employer. Employer was surprised the HR guy knew the business as well as the business folks. Ha

    These days everyone goes straight to their phone, tablet or computer. They’re hooked up to the internet. Most have AirPods or similar. That’s the world we live in. Having better attire isn’t going to do anything for you.

  9. With seats in coach designed to keep me as uncomfortable as possible, I wear functional clothing that is at least a bit comfortable. That usually includes full length jeans and a polo style short sleeve shirt or a short sleeve tee shirt that is not white in color. I do not wear suits, and being retired, I am not looking for business contacts. I usually find men easier to strike up conversations with. From my
    experience it seems that some women seem to think that you are hitting on them if you try to start a conversation with them.

  10. I always feel sad for those who fly in a suit, didn’t know they were looking for “business opportunities”. That’s even sadder.
    I ll waive to you from in front of the curtain as I enjoy another vacation.

  11. I do this in Japan, not in the USA , a Country of drugged slobs.
    Futile advice to impress yanks which are Satan’s gift to this world.
    Yes, I’m French …

  12. This might work for mid-career strivers, but I don’t think a suit and tie is going to impress a decision-maker, who probably is dressed in well-made, comfortable attire. In my experience, the folks who go the extra mile to dress up for a plane tend to either hope for an upgrade, not understand the wear and tear on a nice suit seated on a plane (up front is a bit different, as you might get your suit jacket into the closet), and don’t want to waste the time in the air without a bit of work-related hustle.I’ll dissent on dismissing the watch suggestion. Some of us notice.

  13. Unless I’m at work, a job interview, or a religious service I’m wearing shorts/sweats and a t-shirt. If anyone judges me because of that, they can get bent, they’re probably not worth my time.

  14. Yeah, he’s a broker. Over the years, I’ve closed billions of dollars in commercial real estate transactions across the United States. My go-to “uniform” is a black polo shirt and khaki pants. If the occasion absolutely demands it, I’ll throw on a sport coat. And if a client insisted on a tie? I charge double my hourly rate, and it’s the last time we work together.

    After 31 years in the business, no one cares about what I wear—they care about what I can do. In fact, more clients hire me now than when I used to show up in a tailored suit and Brioni tie every day. And trust me, no one’s giving me stink-eye for my “uniform” if we start talking real estate in business class on a flight.

  15. I fly up front all of the time. I loathe when someone tries to start a conversation with me. I wear my noise cancelation headphones when boarding even if I am not listening to anything. Good to know dressing casually is a secondary protection.

  16. When I got out of the Navy in 1970, my new uniform became a three-piece suit. Later it became two-piece custom-made suit. Later a sports jacket, slacks and a tie. Later it became sports jacket and slacks. No tie. Before I retired, my last job had me mostly wearing khaki slack and blue button-down shirt (no tie).

    I started as a sales-trainee and ended up a President. Along the way, I learned to fit in with my customers. Don’t overdress or underdress. Another valuable tip is to understand the culture where you work.

    I know I might sound prejudicial, but blogger offering his advice is a jerk.

  17. @Bob…it’s folks like you that gives flying a bad name. I hope I never run across you in my travels.

  18. This sounds like the same joker who said you should whisper “Revenue Management” to award booking agents at the airlines because that will magically make the award space appear. What a yutz.

    As to what people dress like – I pretty much don’t care.

  19. I remember years ago, picking my dad up at FRA, and he came off the plane in a tux. Yeah, he was at an event, and had to go straight to the airport afterwards.
    Y’all can be comfortable and well dressed. Sweatpants are overrated. Heck, the people I know who have their outfits tailored will wear it across the Atlantic, hit three days straight of conferences, and go back the other way with it still on. And they’ll look good doing it.
    Turns out the 1920s had some good ideas.

  20. I recently sat adjacent to one of the grossest passengers I came across in all my flights. The bespectacled older guy in a well-ironed pin-stripe suit was picking his nose most of the flight with his bare finger and flicking buggers onto the floor or eating them. At other times he was scratching himself like crazy. When he got up to deplane in a rush and nicely asked to be let into the aisle, it was like dandruff central on his seat and still looked that way on his suit. At least he was friendly and didn’t stink of sweat, but I’ve also come across too many stinky guys in suits. So whether you dress up in a suit or dress up like Senator Fetterman is your style guru, I don’t see why I should care as long as you are clean, aren’t a stink-bomb or otherwise engaged in gross behavior, and are kind and courteous to the passnegers around you.

  21. Several years ago, my son was flying back to Honolulu from Portland OR. I had a college friend who worked for Hawaiian in PDX and she was able to give me an employee pass for my son. At the airport he was able make the flight. Before he boarded, thre station mgr advised my son that he was going to put him in f/c however since he was wearing a tee shirt he said he couldn’t. I tried to teach him about dressing nicely for flying. But we all know teens, they know everything! He learned a real lesson that day.

  22. Wut? People still wear watches?

    What a pathetic way to flaunt wealth-and become a robbery target LOL

  23. @JorgeGeorge – Yes, people still wear watches. Particularly people who aren’t always staring at their phone. Interesting that you’d equate a hundred dollar – brand new – watch with wealth. In Caracas or Port-Au-Prince you’d be right but in the USA chances are your phone is worth more than your watch.

  24. Watches seemed to have sort of made a bit of a comeback. At least smartwatches. But also as a fashion statement.

    As an old school type of person who is like the dog who doesn’t trust new tricks, I still like ink on paper and not having an active and perpetual electronic dog leash on and with me at all times. And for times like that, I love my old cheap digital Casio watch bought probably before Señor Leff could even tell time.

  25. Some of those expensive beaten-up looking sneakers — Golden Goose, thinking of you — are more expensive than the typical dress shoes being worn by most men in suits.

  26. For me, dressing for success (in the sky or on the ground) is in how your clothes fit. If your casual or formal clothes are not tailored to highlight your body, an Armani brand won’t help you. Improper sleeve length on a quality suit is a dead giveaway of someone who does not pay attention to small details, hence is not likely to impress me. Wear clothes with the correct fit..

  27. Pretentious nonsense. It’s actually the opposite: most people will think that you are an airline employee dressed like that because of pass-rider rules – and look down on you.

  28. On many airlines the best dressed passengers are the non-rev’s . . . if they can get a standby seat.

  29. I’m not on a plane to get harrassed by some a hole looking for business opportunities. I’m dressed for comfort on my way to vacation. Keep on moving toward the back and leave me to a movie and a beverage or 3 in peace.

  30. Irritating drivel. Has it not occurred to the author that those of us who regularly fly international F make it a point to enjoy the sleepwear afforded to us by the airlines? There are loads of excellent places to network for business. A shitty domestic F cabin in the USA is seldom one of them.

  31. While the author’s specific suggestion of a suit may be extreme, clean respectful clothing and grooming will always matter. Sure times have evolved and while dressing up for a flight is not necessary, the idea that “anything goes” in a small confined space that is shared for several hours is equally ridiculous. And, to all those who’s response is “leave me alone”, try engaging with your seatmate for just a minute or two. At worst, it’s a polite acknowledgement of their existence and at best, you may enjoy a interesting connection with another human being.

  32. Why isn’t this “dress nicely in a suit and tie or skirt and sweater set” story put next to the “bribery solicitation from airport staff” story. Yes, I wear a coat and tie. Yes, every porter grabs my bag and demands a tip from the rich guy, and almost every gate agent suggests an upgrade that is not complimentary, but for a cash fee from the rich guy. No, my fellow passengers wearing athleisure/pajamas and strung out on ambien and alchohol with eyes glued to screens ears under headphones are not conversational.

  33. Watches are NOT just jewelry. Smartphones run out of juice or you can’t get service, but my mechanical automatic watch just keeps going and going and going…

    I agree, dressing nicely on a plane is a plus in most cases. I’ve found that a nice pair of polished shoes, clean pants (even clean and pressed jeans without holes), and a clean shirt usually winds up getting me slightly better service. And yes, I wear a watch!

    Now, if I’m flying someplace casual like Cabo or Maui that will be warm when I deplane, then yes, I’m flying casual! It all depends on the circumstances.

  34. The only time I would ever wear a suit to travel would be if I were a passenger on the Golgafrinchan Ark Fleet Ship B, which is where I suspect the subject of this article came from. IYKYK.

    I do love a nice analog watch, however.

  35. Interesting, I see someone wearing a suit on a plane and I assume they’re new to business travel and how to value their time or confort or are bad at finding firms to work for that value results and autonomy, vs appearances and conformity and perhaps overworking their employees such that they can’t check in at their hotel to refresh before going to the business mtg b/c “policy”.

    Similaroy, if you’re wearing an expensive watch or designer sneakers, I assume you are clueless on what productive asset classes are, efficient frontier asset allocation portfolio strategy looks like and have friends you secret hate that mutually hate you and each other.

    100% agree wear whatever you want and just be damn friendly and a decent conversationalist. (And polite/not-needy to the crew!)

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