After seven years watching Emily Gilmore wear elegant attire as she grew it is sort of a shift seeing her in normal every day clothing. In fact I would say as much as it is seriously revolutionary. And I am not sure that that is a good thing or not.
When I first saw her in casual clothing, I don't know, it bugged me. Which I felt was strange. Why would it?
I mean I get not wearing those suits that they put her in. For the majority of the show she always wore them, but still, there are at least a few steps in between them and t-shirt and jeans (I'm sadly in that category far too often). Why not dress down to slacks with a random blouse? That would work wouldn't it? Or if it absolutely has to be jeans then why not combine it with an fashionable cardigan?
For the most part though I am fine with it. ASP is being honest, and taking characters in new directions is part of that. I would find it worse when they chase cheap nostalgia as a means of drawing you in. I wasn't really worried that that would happen however. Once I stepped back. Let my personal issues die down I understood what ASP was doing. Emily is lost without Richard. She is no longer sure how to define herself and her clothes are a big part of that.
I see some people think it's too far away from what she used to wear, I was in that camp and I slip back in to it now and then, however, I saw it as something else: imitating Lorelai.
We've seen Emily lean on Lorelai when she doesn't have Richard – during his health scares during the original run – and I think this is more of the same thing. I had a love hate for those moments. And it is mostly love. But the emotions are there. They are so strong. Emily doesn't know who she is or how to dress and she looks to the closest person in her life, Lorelai, and what does she wear? Jeans and t-shirts. When you lose your husband of 50 years, that sudden change in your life is a like a full stop and casual clothing fits that change. So yes from a writing standpoint it makes total sense to me.