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  As the leaves change, so must your wardrobe.  I live in Arkansas where it can be 80f and sunny on the first day of September and 50f and drizzling a day later, so it's most important to dress for the weather.  I'll give you my tips on practicality for the weather, and my tips on style so you don't look like a displaced surfer while tailgating.  

The primary reason we wear clothes is to protect ourselves against the elements.  Wearing shorts past their season or forgetting a jacket means exposing your skin to the elements and if it's too cold, your skin will get dry and flaky and that's no fun for anyone.  Not to mention possibly feeling miserable because of the cold.    All this still too complicated because you just don't want to worry about it?  If you need to, use a weather app that tracks your preferences like Sunshine.  It tracks what temperatures you're most comfortable at and notifies you every day (at a time you choose) of the weather and how you'll be feeling that day.  

First of all, let's talk about shorts.  How long into autumn can you wear them?  Here, you should really think about the weather and how it effects you.  I would say that in my area (south but not deep south) if the weather drops below 65f, you should be wearing long pants.  If you live further south, this may mean if it drops below 75f you need to wear pants to be comfortable.   It doesn't matter if it's sunny or cloudy, if you'll feel a chill, wear pants.  And if you're debating between shorts or pants, pants should always be the default answer unless you're going to a pool party.  

The key to transitioning from summer to fall is really all about layering.  As the summer days lead to chilly nights in September, you may only need a flannel to top your t shirt.  As is gets cooler, you can add more and heavier layers.  Which is great because layers look good on just about everybody, especially with a little planning.  Leave a comment and tell me what your favorite layering piece is!