20 Easy Fall Outfits

Happy October, friends! Can you even believe it’s October?! Like, what?? We’ve had lots of rain and slightly cooler days lately, so hopefully sweater-weather isn’t far beyond.

But until then, we’re in that strange in-between where the calendar reads ‘Boots,’ but the weather says ‘Sandals.’ I shared my formula for transitioning this tricky weather here.

Today I have a Fall Style bonanza post for you…20 easy outfit ideas for the new season! And most everything is back-in-stock for the season, or I’ve linked very similar, in-stock options! I hope they inspire some new combinations for you this month.

sugarplum style spring outfits_5908
Jean Jacket | Scoopneck Tee | Camo Jeans | Booties | Bag Charm | Earrings

sugarplum style spring outfits_5908
‘Salud’ Tee | White Jeans | Leopard Sweater | Similar Booties | Hat

hi sugarplum trench coat spring outfit
Trench | Black Pant | Pump | Leopard Belt | Earring

sugarplum style spring outfits_5908
Twill Utility Jacket | Ruffle Trim Sweater | Similar Tortoise Earring

Military Jacket | Scoopneck Tee | White Jeans | Booties | Monogrammed Tote

camo jacket
Camo Jacket | Ruffle Trim Sweater | Jeans | Booties | Crossbody Bag

hi sugarplum sugarplum style_1832
Fleece Pullover | Slippers

sugarplum style fall outfit
Sweater (love this one, too!!) | Jeans | Booties | Monogrammed Tote

Jean Jacket | Striped Tee | Pendant Necklace | Booties | Tote | Black Jeans

sugarplum style fall outfit
Crewneck Merino Sweater | White Jeans | Similar Boots | Leopard Belt | Tote

Shirtdress (under $50!) | Similar Booties | Leopard Clutch

stripes and tassel fall fashion
Sweater | Striped Tee | Similar Tassel | Black Jeans

Camo Two Ways
Camo Vest | Crewneck Merino Sweater | Similar Boots | Monogrammed Tote | Pearl Cluster Necklace

Similar Sweater | Jeans | Booties | Tassel Earrings

blush pink utility jacket
Twill Utility Jacket | Crewneck Merino Sweater | Leopard Belt | Tassel Earrings | High-Rise Jeans

Camo Two Ways
Similar Sweater | Camo Jeans | Booties | Similar Bag

hi sugarplum jcrew schoolboy blazer
Schoolboy Blazer | ‘Love First’ Tee | Cropped Jeans | Leopard Flats | Tassel Earrings

leopard sweater outfit
Chambray Shirt (40% off!) | Leopard Sweater | White Jeans

I can’t round up Fall styles without including this fleece button cardi…one of the most popular items for HSP readers four years straight!! It comes in a slew of colors and is under $40.

hi sugarplum dressing room diaries
Fleece-Button Cardi

And when it comes to Fall travel, my go-to outfit is pretty much joggers and jean jacket!

sugarplum style spring travel outfit
Jean Jacket | Scoopneck Tee | Fleece Joggers | Sneakers | Tote | Hat | Crossbody Bag

Okay, clearly my Fall wardrobe essentials include this crewneck sweater, a twill utility jacket, and leopard belt! Those three pieces are staples and found their way into most outfits.

And if you’re looking for more inspiration, check out last year’s 31-Days of Fall Style for a whole month of outfit ideas! #bamwhat Now if only Texas would get that Fall memo!



Leave a Comment


  1. I love that camel trench coat of yours! It’s beautiful – perfect for keeping warm and looking stylish at the same time! 🙂

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 10.1.18 Reply
  2. SO INSPIRED!!!! Such great looks!

    Posted 10.1.18 Reply
  3. Sevahn wrote:

    I just started October 1st with the purchase of the pearl cluster necklace thank you very much! It’s going to be paired with a lot of your inspirational items as Sheaffer says, starting with the fleece button cardi (in red) which is in my shopping cart except I did not bring my Nordstrom card with me to work today #won’tdothatagain!

    Posted 10.1.18 Reply
  4. Kerri wrote:

    Love this post, and thank you for continuing to get me dressed every morning! Pinned so many great outfits, and the best part is that I have been inspired by you for so long, I own a lot of the pieces already! Now I have some new ideas for how to wear them. Thanks a million!

    Posted 10.1.18 Reply
    • Cassie wrote:

      Thank you so much, Kerri!! I’m thrilled you liked the post!

      Posted 10.2.18 Reply
  5. Jayni B wrote:

    Who in the world knew you could pair pink and camo???? Say what?! I can NOT wait to try!

    Posted 10.1.18 Reply
    • Cassie wrote:

      Pink is my fave with camo!! Well, and stripes! 🙂 I’m thrilled I inspired a new outfit idea! xo

      Posted 10.2.18 Reply
  6. Nikki wrote:

    My carts are full…now I just need temps to drop 35 degrees!

    Posted 10.2.18 Reply
  7. Mary wrote:

    What size are you and your mom wearing in the fleece button cardi?

    Posted 10.2.18 Reply
  8. Susan wrote:

    Can you please refresh my memory on the anoraks and raincoats you recommended? I can’t seem to find them again.

    Posted 11.6.18 Reply
  9. Donna stewart wrote:

    When has it been ok to wear white after labor day…or am I just very old school.

    Posted 9.18.20 Reply
    • Cassie wrote:

      There are no ‘rules’ in fashion anymore! I pay more attention to the fabric, and whether or not it’s seasonal (like eyelet and linen). But everyone has to do what they’re most comfortable with! xo. C

      Posted 9.18.20 Reply
  10. Lizzie wrote:

    I know this is an old post but where is your tan hat from in the jean jacket outfit? I don’t see that linked – thanks!

    Posted 11.29.20 Reply