Being woken up at 7:10 am instead of 5:45 am sends Lorelai intoa panic. We learn that all her nice clothes are at the drycleaners, and she was planning to pick them up and get dressed in her blue suit with the flippy skirt before she took Rory to school. She fumbles through a drawer, then in the next scene she is hurrying downstairs dressed in cut off denim shorts, a pink tie-dyed tee-shirt, and cowboy boots – apparently the only clean clothes she has to wear.
The trouble is that she opens the closet and we see clothes hanging up in there. Maybe they’re not great clothes, but most of them would be better than going to Rory’s school dressed in denim cut-offs and boots. For that matter, why does she need to wear boots? You don’t send shoes to a dry-cleaner, so she should still have normal shoes to wear. And what time did she plan on going to the dry-cleaner anyway – Rory’s school day starts at around 8 am and it’s a half hour drive, so does the dry-cleaner in Stars Hollow open around 6.30 am?
It’s hard not to reach the conclusion that Lorelai had a very specific outfit in mind – the blue suit with the flippy skirt – and since she isn’t able to wear it due to her own poor time-management skills, is determined to wear something completely unsuitable in a fit of pique.