Single layers (and no shoes) represent Ed's emotional vulnerability/openness and self reflection.
It's a common symbolism device to either have characters put on tons of layers when they are feeling vulnerable (Dean Winchester I'm looking at you) or go down to single layer when they are opening up. Ed's clothing is no exception.
Season One
The first time we see Ed in single layers is when he switches clothes with Stede. While during this whole episode, Ed is opening up, he makes altering life decisions while in Stede's outfit. First, the whole scene in the crow's nest where he takes seriously Stede's proposal to continue learning about each other's lives, and second when he lies to Izzy about planning to kill Stede.
I think the choice of black and white, the classic good and bad trope, can be read into as well. Stede is in the black leathers of Blackbeard with lighter color jewelry around his neck, showing the heaviness of the Blackbeard role and crew, while Ed is wearing a white shirt with a black cravat, showing Stede's way of piracy giving him hope while having a bit of Blackbeard's heaviness still there.
In 1x7, This is Happening, Ed goes down to one layer — the t-shirt.) Ed drops his jacket and goes down to a single layer right before Lucius rips into him about Stede's feelings for him and he stays down in these layers as they eat the snake.
Ed's emotions are bare, at the forefront. He is not only realizing Stede's feelings for him, but also letting his feelings come out.
And his shirt is purple — symbolizing Ed's love for Stede. (Sidenote: I love that blue is Stede's color and red is Ed's and they combine for a beautiful purple throughout the show.)
Both Ed and Stede are in single layers the first time they kiss. Ed confesses his love (what makes Ed happy is you) while they sit next to each other on the beach. Both of them are vulnerable, open, especially Ed. They are both terrified, figuring themselves and each other out.
Ed continues to be in single layers as he sits on the dock waiting for Stede. The color theme of purple is once again used to represent Ed's emotional state.
The infamous breakup robe. While Ed has gone back to the Revenge, trying to be just Ed, back to the crew that allowed him to be himself (all but one person that is), he stays in the breakup robe, sans shirt, most of the time.
Until he has to put the mask and persona of Blackbeard back on, he is open, and emotional in front of Lucius and then the crew.
He is also shoeless during most of these scenes. While Ed being shoeless is more prevalent in season two, I think it ties into a deeper level of self reflection.
Season Two
Ed is down to only a black shirt and pants in the grav(e)y basket.
This time the t-shirt is black — symbolizing Ed's dark headspace. But once again, it's all about his emotions and Ed really feeling them. He is self-reflecting, looking into himself and realizing what he wants in life, what he thinks of himself, and finally deciding that ultimately, he wants to live.
There is the moment in Purgatory where Ed makes a shoe and puts it on, symbolizing one foot in the grave. But by the time Ed climbs to the cliff edge, he is back down to no shoes. This symbolizes two things: 1) he is no longer one foot in the grave (foreshadowing) 2) that he is about to do more self reflecting.
The combination of one-layer and no shoes is when Ed is most open emotionally. He now realizes his own feelings about himself, and when he hits the water, he decides to fight to live. Yes, mer!Stede is part of it, his love for Stede cannot be hidden, it is out in the open, the shining beacon of light and hope.
I've talked about it before but the editing of the MerStede scene is amazing. The last shot in the water as Ed sinks down is Ed in all black, surrounded by dark waters, his feet the most prominent in the shot. This cuts immediately to Stede's feet wading into the holds water, joining Ed in both worlds.
In all of 2x5, Ed is in the rice sack (and I'd be remiss not to mention the cat collar and bell.) He starts out wearing sandals: during the talks with the crew, Stede, the door, and Lucius. While Ed is trying to make up for everything, he is not fully committed emotionally to everything.
Not until two things happen: Lucius pushes him overboard into the water — the symbolism of water as rebirth, understanding, growth is very loud this season — and in the process knocks his shoes off. While it is a comedic beat and parallel to Lucius's shoes coming off when he pushes him overboard it has a deeper meaning.
Ed fully lets himself feel and tap into his emotions — sit with himself if you will — once he talks with Fang. He learns that something he did in the past that he thought was fun was actually hurtful to the other person. He genuinely apologizes for that (the opposite of the corporate apology from earlier.)
He then continues that openness and vulnerability with Stede on the deck. Telling Stede exactly what he needs — to take it slow — and knowing that Stede won't do the exact opposite (what happened constantly last season with a certain character cause they thought it was "best") but he knows Stede will listen to and respect him. This moment shows how Ed is not only legit apologizing and realizing his actions, but letting himself be open and vulnerable again.
The last scene I want to point out is the moment before and morning after they sleep together.
The last shot we see of them that night, Ed sits on the bed, his hair down, his jacket off — down to one layer — as he looks lovingly to Stede. We can read many emotions on his face as the two of them are surrounded by all of the colors that we know to represent the couple — yellow, red, and purple.
In a parallel to the night before, the next morning Stede is shirtless but covered from the waist down, while Ed is covered. He is wearing Stede's robe, wrapped in one layer of comfort. The outer layer is blue — both Stede's color and the color of the ocean (there's that rebirth and change symbolism again) — with purple inner lining.
Both of these moments contain physical, mental, and emotional vulnerability for Ed. Ed has never been shy about explaining himself, but he is now starting to understand himself and process these emotions.
When Ed is in single layers and no shoes, it is when he is at his most vulnerable, gets to feel and express his emotions the most.
When he's Ed.
I may have missed some moments but these are the ones that stuck out to me the most. I also didn't dive into Stede here, but that could be a whole other essay.
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