Is it still appropriate to dress like a bag-lady?

 Sweater - SMK - New Classics, Button up - 3.1 Phillip Lim, Pants - TOPMAN, Shoes - Prada

Serious question: When do you know it's time to ditch the layers? Is there a certain day or month? or announcement?? I feel like every year I miss the memo. All my friends are whipping out the shorts and the lighter layers, but I still grab my turtlenecks and my long sleeves. 
Yes, I know, you're probably thinking "Paul, weren't you in shorts just a few days ago?" Yes I was, but still. When can I be 100% sure that I won't be the sore thumb in my layers? 

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