My worst one was when doing an Alaskan cruise with a good friend. I lived in Los Angeles, she in Miami, so we flew there separately. I got to the airport only to be told that the tickets my TA gave me were actually for a different airline, owned by the one on my ticket. I have mobility problems and had to haul my stuff through LAX to the right airline. Only to find out that my flight had been rescheduled....3 hours earlier! I was furious. Airline agent called my TA, who tried to claim that she had told me about the change (she had not), then added insult to injury by saying that the fact that I was so old (I was 52 at the time) and had a bad memory was not her fault. Luckily the airline agent didn't believe her either and got me on a flight that allowed me to get to the ship on time.
When I got back, I wrote a furious letter to the TA owner. Never got a reply. Never dealt with them again.
The scarey thing was that I had been using this TA company for years. They just hired someone new who screwed up.
I have no idea whether they had any fashion sense.....didn't care.