I’ve been in a mega-long phase in my life where my approach to a given outfit goes in order of the following criteria: comfort, chicness, coolitude, sexiness.

Aaaaaah! Yep.
No good.

See, it’s the order that worries me cause when you start with comfort, I heard it’s a bad sign. It always seems like to be chic, you have to accept a certain amount of discomfort with every outfit. Otherwise, you’re flirting with laziness.

Pfffff, means I am on the wrong path. I do flirt a lot!

And that is why, whenever I pass a girl on the street who seems to have the same priorities as I do, I literally fall all over myself. For example, here you have Katharina. She’s not cold and she could practically run a half marathon in her outfit, but she still looks super cool!
Look how happy she looks!

At the same time, I am finding that I end up asking myself all the time just how far I can push it…

With my status as a freelancer, I don’t have much of any wardrobe constraints…

Should I push myself to wear something other than jeans and ballet flats? Should I really get myself into a pair of heels and a skirt just for fun? Mmmmmm…

How would you negotiate it? What are your priorities when choosing an outfit?
Do you put comfort first or are you trying to make a little effort everyday, even if it means being slightly uncomfortable?