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.

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