Y’all—September has arrived! 

So far here in New York City, she is looking and feeling lovely outside (one step at a time!) Now is the time for cooler weather, pumpkin spice lattes, layered outfits, seasonal home decor, and fall comfort entertainment! 

When we don’t want to take brisk walks or head over to our local pumpkin patch, we cozy up on the couch and prepare ourselves for a night (or day, let’s be real) of comforting entertainment (a.k.a. comfort rewatches!) 

If you are looking for a feeling of nostalgia, comfort, relaxation, or even some spookiness—we have the list for you! Here are our 5 ultimate fall movies/series to watch this season:

1. When Harry Met Sally – Available on MAX

This is a classic New York City rom-com that has many elements of fall to it. It’s comforting, romantic, hilarious, and aesthetically pleasing to watch. With some of the best fall fashion in any film ever, it makes me ready to throw on a turtleneck sweater, a comfy pair of jeans, grab a hot cup of coffee, and feel all fuzzy inside.

2. You’ve Got Mail – Available on MAX

Another fall classic New York City rom-com that takes place through the fall (also starring the iconic Meg Ryan). Romance, books, an undeniable fashion—it makes for an ultimate fall foliage film. 

3. Halloweentown – Available on Disney +

Okay—allow me to explain. This was one of my favorites growing up. I always do a rewatch of this around this season and it just makes me feel all warm and fuzzy inside! There’s nothing like a good childhood movie to make you feel happy and festive!

4. Gilmore Girls – Available on Netflix

Need I say more?! There is nothing like a rewatch of Gilmore Girls during the fall. Apparently, half of all Gilmore Girls episodes take place during the fall time. That being said, it is only fair to rewatch the witty banter between these delightful characters.

5. Wednesday – Available on Netflix

Okay this is a new favorite! We watched this last year and will definitely be making it a part of our fall entertainment rotation. It is a little spooky, funny, and overall gives off a really nice Halloween aesthetic that is super fun and exciting to enjoy!