September Monthly Outfit Calendar

Fall Monthly Outfit Calendar | 30+ Outfit Ideas

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And just like that, it’s September. Brisk mornings, steaming hot drinks, and delicious-smelling candles are right around the corner. If you want to enjoy this fall season without constantly thinking about what you’re going to wear, then you’ve come to the right place. Because here you’ll find a September (Or October- depending on your weather) monthly outfit calendar supplying you with outfit ideas for every day this month!

This post is sponsored by Nordstrom. Thank you for supporting the brands that support My Chic Obsession.

We talk a lot about basics here- and for good reason. Instead of purchasing one statement dress that can be worn only once (even if it’s gorrrrg), wardrobe basics can maximize your wardrobe, so when you purchase one thing you can wear it all season long.

And if you want to maximize your time as well as your wardrobe, Nordstrom is a great place to shop as you can get your whole fall wardrobe in just one place. With brands from Halogen to Nordstrom Signature (their luxury brand), you can outfit your autumn closet no matter your budget.

By following this outfit calendar and supplementing your wardrobe with these key staples from Nordstrom, you can have 30+ outfits that all look fresh and stylish. No one and done outfits here!

First, let’s take a look at the key pieces:

Fall Wardrobe Staples

Let’s break it down!


Even though they’re wardrobe basics, don’t mistake that for boring. In order to create a myriad of looks that can look fresh and different, make sure you have varying sleeve lengths (long and short), different materials (such as cashmere and denim), and multiple prints and colors (solids and stripes).


Thankfully, in a fall wardrobe, you don’t need a ton of jeans. Solid-colored jeans, though simple, play a big role in your wardrobe. By swapping out your shirts, you can create outfits that feel new. Dark wash and black are your go-tos and once you got those covered, incorporate a pair of leather leggings or plaid pants into your wardrobe for your casual yet stylish outfits.


From date nights to Thanksgiving dinners, everyone needs a few dresses that elevate their autumn looks! This September, a sweater dress and slip dress can work for all the occasions when you want to feel a little bit dressier. And by different layers and your choice of shoes, you can make these pieces work for both slightly warmer and chillier weather.


Lots of jackets here and for good reason! Fall is the season of layers and the perfect time to add interest and style to your outfit. All of these coats and jackets serve a purpose in your wardrobe and can instantly change the look of your outfit.

Related: How to Wear a Coat in 2 Different Ways for a Classic Look


If you want to take a break from jeans, slip on a skirt. Comfy yet elevated, skirts are a great casual chic piece to have in your wardrobe. And when selected in a moody floral or animal print, you’ll look perfect for fall.


August brought strappy sandals and espadrilles. This new month brings the opportunity to break out styles that would have been too hot to wear previously. From ankle boots to loafers, just like outerwear, the right shoes can change the whole vibe of your look.


No outfit is complete without accessories. You’ve already got your go-tos (gold hoops, dainty necklace), and now is the time to bring out your fall-specific pieces. You’ll need a scarf for cozying up and a belt for belting over your sweater dress and blazers.

Now here’s how all these pieces can be worn every day of this month:

September Monthly Outfit Calendar

Whether you need outfits for the office or want casual chic looks for traveling, this outfit calendar will get you outfitted all season long.

Want to see these fall looks in action? Check out 6 Go-To Classic Fall Outfit Formulas Modeled on Two Different Body Types!


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.