I always said that my kids flew like they’d been on a 3 day bender
I like to wear my dressy sweatpants
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You better believe if I’m spending hours in a tiny seat and have to use those airplane bathrooms, I’m wearing elastic waistband, loose and/or stretchy pants!
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I wear nice Athleta leggings, a long top/blouse, cotton blazer and my comfy Taos white sneakers to travel. My outfit looks put together and is comfortable to wear on a plane. I will be honest and say I absolutely hate when people travel in pj bottoms and flip flops. This is a plane full of strangers, not your home. But that’s just me!
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I’m not judgmental of fashion choices. I can always close my eyes.
What I don’t like is when people are on the plane coughing and sneezing while not wearing masks. I definitely become very internally judgy about that. I hate getting sick after traveling.
Or people who are noisy or smell bad (not counting babies and toddlers who can’t help it).
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Flip flops is the worst possible choice of footwear on a plane! Beats even high heels. 
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My vote for worst footwear is when people take their shoes off on the plane and have stinky feet!
Delete because I was getting way off topic
Frontier is giving one free checked bag this summer. Not sure when it starts or ends, but clearly trying to attract SW passengers.
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Their 2* rating on TripAdvisor is a turnoff… (That said I had a lot of trepidation about flying Silver to key west from, I think, FLL as it had similar reviews, but it was absolutely fine the one time we did it)
Oh I don’t fly Frontier and even the free bag check wouldn’t get me to do it.
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Your comment about gate agent reminded me of our recent SW flights (from Hawaii to mainland). We did early bird, and my husband was A60 and I was B1. I called SW and they said just board with my husband and I would be fine. I asked when we checked in, and the woman said the same. Get to the gate and I try to board with my husband, and gate agent says I can’t board with husband, and it’s her call. It was OK - I still got aisle seat beside my husband’s aisle seat, but I was rather frustrated.
Yes, many things seem to be ultimately determined by the gate agent. (Not just on Southwest.) Any time I’ve needed permission for something, I’ve generally had good results by keeping an eye on the gate agent after they start standing by the gate, and coming up to ask at a moment when it seems like they are not too busy, before boarding starts.
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My husband and I both have status on Alaska, C26 not, so we are B and C26 is E boarding group (and the equivalent on American, where we sometimes reluctantly use our Alaska miles). C is 4” taller than I am and definitely doesn’t look like a “kid”, but we have always put them between us on boarding these flights and not once has the gate agent stopped them. In fact last year before my husband got status - I was boarding with B to ensure overhead space - guy in front asked if his gf could join him so I asked for my fam too and the gate agent said sure to both! So yeah sometimes you just get them in a good mood I guess.
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I have been on both Alaska and Southwest planes with the newer larger overhead bins that should allow for one full size carry on per passenger.
However, optimizing the overhead space means that passengers have to know how to put their carry on bags in the bins properly (and not try to bring on bags that are too big or whose wheels and handles extend beyond the size limit). Unfortunately, many passengers do not seem to know how to put their carry on bags in the bins properly, so getting overhead bin space can still be competitive when it really should not be.
In the image below, the bin on the right has the newer larger bin with the bags placed properly. The bin on the left is an older smaller bin, but many passengers put their bags that way even when the bin is the newer larger type, wasting the extra space.
Yet Alaska still always warns, on full flights, that passengers boarding in E might not get bin space and try get them to gate check.
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Seems like they really should have some example economy class seats and overhead bins (of the various kinds that may be in aircraft docking at the gates) in the gate areas so that passengers can test fit their carry on bags before boarding. They should have pictoral instructions on how to place bags in each kind of bin.
Of course, when Southwest stops including checked bags with tickets, overhead bin space will be more competitive on Southwest flights, like with other airlines (at least until they started being like Frontier and Spirit and charging for carry ons in the overhead bin).
Per policy the gate agent was correct, unless you are on a companion pass. That’s a case where the non operational people didn’t know the rule.
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I’ve seen these in the bins themselves…and seen people ignore them totally
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When I’ve boarded planes with these new bins, it seems that the bins themselves have signs with diagrams? And if someone doesn’t understand how to put their bag in the bin, it’s not impossible for other passengers and crew to flip the wrongly placed bag up to make room.
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Which goes back to my earlier gripe about with early bird you are paying,but you don’t know exactly what you are paying for. It’s happened to us once too that we have been separated by group on one reservation with early bird before.