30 Days of Fall Outfits

Cheers to Friday, loves! We are in the thick of our son’s high-school Homecoming Week, and I’m loving every second of it! Wednesday night we hosted the mum exchange, last night was the big football game, and tomorrow is the dance. Next year, he’ll have his driver’s license, so I’m really savoring this last opportunity to be so involved. Even if it’s only as chauffeur!

But ohemgee…wait until you see him in his suit! My mama heart can barely stand how grown-up and handsome he’s become! Remember the younger years when your kids insist they’ll marry you someday?! Yeah, we’re not there anymore. #gulp

Let’s chat the mother of all Fall Fashion posts before I start blubbering, shall we?! I’ve been getting so many requests for more Fall/Winter style inspiration…so I thought it’d be fun to round up 30 (yes, I said thirty!) of my cool-weather favorites. Basically, a whole month’s worth of outfit ideas for you, including links to re-create them yourself! How’s that for a Fri-Yay!?

Rainboots | Crossbody Bag (back in stock!) | Sunglasses


Sweater | Jeans | Watch | Ring
Jeans | Boots (worn folded down) | Hoop Earrings


Bag (similar) | Hoop Earrings | Watch | Scarf

Wowza, maybe 30 was a little ambitious…but once I get going creating outfits, I have trouble turning it off! I hope this post inspired you to look inside your closet for new combinations to wear this Fall…and stay tuned for new inspiration in the coming months. Happy weekend, lovebugs!


{Shop Fall Wardrobe Essentials}

*This post created in collaboration with Nordstrom, but all clothes, ideas, and wistful Fall nostalgia are my own. Thank you for supporting the brands that support Hi Sugarplum!*

Leave a Comment


  1. Your favorite tan peacoat is on sale for $37!! Does it run tts or small like the website says? Thanks!!

    Posted 11.4.16 Reply
    • It runs small for sure, I sized up two!! You'd be okay sizing up one, but I like a little more room for thick sweaters. xo

      Posted 11.4.16 Reply
  2. OH MY GOODNESS! 30 days of TOTAL DARLINGNESS!!!!! Well done, friend!

    Posted 11.4.16 Reply
  3. Christina wrote:

    Awesome post, Cassie! Such great inspiration. Enjoy this week with your son! My oldest is 10…It really does go by fast.

    Posted 11.4.16 Reply
  4. Jenny wrote:

    Goodness! So much cuteness in this post! I feel like I haven't gotten out of my jammies in days…now I'm looking for an excuse to get dressed for fall!
    Thanks the sharing!

    Posted 11.4.16 Reply
  5. Kim wrote:

    Love you outfit posts and ideas so much. I want to recreate every one of them. What socks do you wear with booties?

    Posted 11.4.16 Reply
    • I wear really low-ankle socks…my fave I've found so far are from Old Navy. xo

      Posted 11.4.16 Reply
  6. Well, dang! Of course I love them all. It was an "oooh" "ahhh" fireworks watching experience. I would see one outfit and think, "That's definitely my favorite," but then I would scroll and think the same of the next one. Great round up!

    Posted 11.4.16 Reply
  7. Anonymous wrote:

    What, no link for the adorable dog! Love your stuff, always in good taste.

    Posted 11.4.16 Reply
    • Never!! She's ours forever! 😉 xoxox

      Posted 11.4.16 Reply
  8. My Nordy's card is going to explode; so much cute stuff! A couple questions – 1. Does the grey hooded sweater run big (not sure whether to get XXS or XS) and 2. With the $37 camel coat, did you have the sleeves shortened? I am tempted as I got a medium and I feel like I'm wearing my Mommy's coat!

    Posted 11.4.16 Reply
    • Yes, that cardi runs large, I'm in an XXS…and the coat arms are a tad long on me, but not something I notice (or bothers me), when I'm wearing a sweater, etc underneath it. xo

      Posted 11.4.16 Reply
  9. Anonymous wrote:

    Love all your outfits–you always look great! Have a wonderful weekend 🙂

    Posted 11.4.16 Reply
    • Thanks so much! happy weekend to you! xo

      Posted 11.4.16 Reply
  10. Britta wrote:

    Loved this! The buffalo check button up shirt (worn with leggings) is linking to the gingham shirt. Would love to have the link to the buffalo one!

    Posted 11.6.16 Reply
    • That one is from Old Navy last year, so I linked the closest I could find this season. xo

      Posted 11.7.16 Reply
  11. Rio wrote:

    Love the layers!

    Posted 11.7.16 Reply
  12. Well that was 🎵AWESOME🎵! I've saved several of these to my phone to use when I go shopping. Thanks Cassie!!

    Posted 11.8.16 Reply
  13. Cassie, this post was amazing! You are so stylish mama!!

    Posted 11.11.16 Reply