Prelims: This question is a compilation of questions that Jesus is using to discuss John The Baptist and his role in the society at the time with respect to the crowd that is now thronging to Jesus, as well as John’s role with Christ as His forerunner. So it’s a bit confusing, and there’s a lot here. I’ve edited this several times trying to distill the questions and answers. But as always with our Lord, there’s always much more there than what is simply on the surface.
The quote from Matthew 11:7-10:
“As they (John’s disciples) were going off, Jesus began to speak to the crowds about John, ‘What did you go out to the desert to see? A reed swayed by the wind? Then what did you go out to see? Someone dressed in fine clothing? Those who wear fine clothing are in royal palaces. Then why did you go out? To see a prophet? Yes, I tell you, and more than a prophet (Matt 11:7-10). This is the one about whom it is written: ‘Behold, I am sending my messenger ahead of you; he will prepare your way before you.’”
The Context: Our Lord’s initial response at the beginning of this chapter is to 
John the Baptist’s disciples. Namely, He is responding to John’s inquiry about whether Jesus is the Messiah. After His reply, our Lord turns to the crowd to address John the Baptist’s role in Salvation history. Accordingly, He asks these questions. Even though our Lord asks these in rapid succession, let’s take these one by one.
The Question(s): “What did you go out to the desert to see? A reed swayed by the wind?”
Curiosity seekers often travel to sites of spectacle or scenes of purported wonders to report to others that they were there, or saw the great sight. In today’s world, this can be anything from “rubber-necking” at a car wreck on a highway to travelling to a last performance of a noted musician. Our Lord’s follow-up question bends toward this: “a reed swayed by the wind” indicated a particular type of tall cane that would flatten when the wind blows and then resume its full stature., that it would have been a noted wonder to see the thing being blown down and then rising up again.
There’s me and my family in the way back part of the way back.
One of the reasons I went to St. Louis in 1999 was to see St. John Paul II. Among many reasons for going was to say that I had been there. Nothing wrong with that, mind you, but in full disclosure, we all do this to some extent.
(In Matt 3:5, the evangelist tells us of great numbers from Jerusalem, Judea, and the country around Jordan, went out into the wilderness of Judea, where John came preaching, to hear him, and be baptized by him). Some people consider the mid-west “the wilderness” or fly-over-land!
The next question presumes that you just answered “No” to the first series.
“Then what did you go out to see? Someone dressed in fine clothing? Those who wear fine clothing are in royal palaces.”
Again, the question goes to the motive of why you would go out to see John in the desert. It couldn’t be for John’s fine clothing. He wore camel skins and rags. Again, the spectacle of having said that you saw a prophet. For some, this was all. John was known for his exhortations and his zeal.
In my pilgrimage to see St. JPII, I knew he’d be wearing white, and some sort of cassock. I didn’t go to see him for the fashion show. I wanted to see and hear John Paul II exhort our nation to the spiritual greatness he knew we were capable of achieving. We were not disappointed.
“Then why did you go out? To see a prophet?”
You can tell your grandchildren that you saw the great prophet, John the Baptist. This answer almost makes you holy. Almost makes you famous. It’s like going to see the Pope: you can say that you were there, that the event impacted you and your legacy.
Back to John the Baptist – OK, so you were there, but were you listening to him? Maybe you went out to see him for his preaching. You heard that he was a prophet and wanted to hear him for your own satisfaction. You heard he was strange and speaking on the imminent coming of The Christ. He had secrets to tell, and you wanted to be “in the know”.
Then Jesus tells us that John was more than a prophet in that John is His forerunner.
Listening to St. John Paul II that day, I don’t recall his exact homily (the 
captioning on the screen was inexact back then), but I recall his demeanor and his general attitude of love for what he was doing there at that moment: Celebrating the Mass.
I do recall that he announced that because of his intercessory action with the Governor of Missouri, that a man that was to be executed was taken off death row.
I didn’t go there expecting to see miracles or great pomp and ceremony. After all, Mass in a convention center is a messy, crowded business. Hardly glamorous. I did expect John Paul to stay true to the teachings of the Faith. To stand for the family, for life, for religious freedom. And he did that. And so much more.