Not sure what you mean with "Looking Cool"
. Do you mean "Looking Hip-Hop", "Looking Hip", or dressing "lightly" for hot days?
I have this discussion with my Spanish significant other from time to time and she thinks (as do many in her/our generation here in Spain) that teenagers have never dressed worse in history!
Many say Spanish teenagers have lost all sense of "SENSE" with regards to the clothes they choose to wear. Teenagers, these days, are dressing the same (or
worse) as most of the teenagers in the USA what with their droopy pants (girls and boys), tattered bell-bottom jeans (tattered part dragging the ground), tennis shoes, ragged, shirts, not to mention the piercings, tattoos, track suits, and the like.
This "look" doesn't bother me because, well, I'm used to it and *I* think they're just dressing comfortably. SHE assesses that one can dress comfortably while still dressing nicely. Hmmm.. I've personally yet to find that to be true.
During these hot summer months you won't find many girls wearing the shorts, T-shirt, and tennis shoes combination.
If you "expand" this "Packing" forum category to show topics from the last 100 days you'll see many similar threads including, "Madrid - Warm next week - what to wear?", "Madrid - What to Wear mid-May", "What to wear if you are a 13 year old boy?", & "what to wear?"
Good luck! Saludos, MadridMan