Hi Sugarplum!

{5 Ways} Fall Boots

I don’t know about your area, but November blew in like a lion for us…with rain and cold temperatures. Granted, ‘cold’ for us this time of year is still in the 60s, but definitely enough to put away the sandals, and transition to closed-toe shoes and boots. I’ve shown you a fair share of boot-outfits in the past few weeks, but I thought it’d be fun to do a {5 Ways} post on the different styles of Fall boots, and ideas for how to wear each of them.
I’ll warn you though, I got this post idea late Sunday afternoon…when my hair was past it’s expiration date, my face was naked, and my camera decided to be a pain in my patootie. But our sweet Maggie makes up for my sub-par pictures!
Hi Sugarplum | {5 Ways} to Wear Fall Boots

{Riding Boots}

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Hi Sugarplum | {5 Ways} to Wear Fall Boots

{Knee High Wedge Boots}

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Wedge Boots | Utility Vest | Plaid Shirt (similar) | Jeans

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Wedge Boots | Utility Vest | Plaid Shirt (similar) | Jeans | Bag

Hi Sugarplum | {5 Ways} to Wear Fall Boots

{Flat Booties}

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Dress (similar) | Jean Jacket | Scarf (similar) | Booties (similar)

Hi Sugarplum | {5 Ways} to Wear Fall Boots

{Tall Booties}

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Tall Booties | Distressed Jeans | Striped Top
Plaid Scarf (similar) | Military Jacket (similar)

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Tall Booties | Distressed Jeans | Striped Top
Plaid Scarf (similar) | Military Jacket (similar)

Mr. SP took this round of pics for me…and his required payment was that his beloved SF Giants make at least one appearance…but hats off to the KC Royals for a magical season. #seewhatIdidthere

Hi Sugarplum | {5 Ways} to Wear Fall Boots

{Ankle Booties} 

 Hi Sugarplum | {5 Ways} to Wear Fall Boots
Ankle Booties (similar) | Blouse | Skirt (similar)

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Heeled Booties (similar) | Blouse | Skirt (similar) | Tights | Leopard Clutch (similar)

A slight bootcut jean has made it’s way back into my regular rotation…it really is the most flattering shape…and I like to pair heeled booties with them, as well. I ran out of light before I could try the outfit on for you, but I wanted to show you the idea.

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Heeled Booties (similar) | Blouse | Dark Baby Bootcut Jeans (40% off!)

Along with boots and scarves, my favorite Fall wardrobe additions are jackets and coats. We don’t get to wear them very long around here, so I pull them out as soon as chilly days arrive. Did you know Nordstrom has an entire selection priced under $200?? Considering they are staples you’ll keep for years, that’s a great deal! But at those prices, I tend to add a new one to the mix every so often. Sure they are meant to keep us warm, but they can also elevate an outfit! #priorities

Hi Sugarplum | {5 Ways} to Wear Fall Boots
Coat (similar) | Hat
What is your favorite Fall boot style? Can you even pick just one?! I love them all…except maybe the lace-ups, those aren’t really my jam. See more {5 Ways} posts here…and more boot outfits here and here.

Update! I just noticed Nordstrom announced their 40% off clearance sale today!!

{Shop Fall Boots}

{Shop Coats Under $200!}

** This post is created in collaboration with Nordstrom. But the outfits, clothing selections, and boot-scooting are all mine! Thank you for supporting the sponsors that keep this blog running! **


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  1. Jillian says: November 5, 2014 at 1:10 pm

    super cute outfits cassie! i love that white sweater 🙂 xo jillian – cornflake dreams

    Reply
  2. Decor To Adore says: November 5, 2014 at 2:03 pm

    Completely adorable! Could you please tell me the maker of the plaid jacket you are wearing? I realize that it may no longer be available in stores but a girl can dream.

    Reply
  3. Erin @ Crafts and Sutch says: November 5, 2014 at 2:09 pm

    As always, adorable! I love the scarf you have on with the tall booties and that plaid pea coat! So fun!

    Reply
  4. sarah m. dorsey says: November 5, 2014 at 2:40 pm

    I always love your outfit choices, super cute, as always! 🙂

    Reply
  5. Team Clancy says: November 5, 2014 at 3:15 pm

    Thank you for this post!!!! Super cute outfits!

    Reply
  6. Andrea says: November 5, 2014 at 3:28 pm

    Always loving the military vest!!! I was inspired to quick buy one on a Friday two weeks ago after one of your posts. I ran to Marshall's (the nearest store that might carry such a thing) and found one in the army green. I wore the next day on a wine tasting weekend (yes we have a lot of vineyards in MINNESOTA!) and today I have it on with wool dress pants (Banana Republic and Loft are my go-to for work), ankle boots, a silky button down, and accessories (scarf near by in case I get chilly too)! It is SOOO versitile. Have a WONDERFUL day! Half way to the weekend!

    Reply
  7. Lisa Nichols says: November 5, 2014 at 4:20 pm

    I need you to do some hair tutorials! Love your clothes & your hair! My hair is cut very similar to yours. Thx!

    Reply
  8. Simply LKJ says: November 5, 2014 at 4:58 pm

    So adorable!

    Reply
  9. Michele says: November 5, 2014 at 6:11 pm

    I love boot season! You look fabulous in all of these, and I especially love the black top with the sequined skirt and grey booties. This would be a great holiday party outfit!

    Reply
  10. Carrie says: November 5, 2014 at 6:48 pm

    Outfits aside, you always rock the cutest pony tail… I love those gold colored wedge boots!

    Reply
  11. Michaela says: November 5, 2014 at 7:40 pm

    Cute boots + GO GIANTS 🙂 hehe. I love that your husband loves them!

    Reply
  12. Courtney {a thoughtful place} says: November 5, 2014 at 8:13 pm

    Darling! And I agree with Michele. . adore the gray bootie outfit on you. And I definitely did some damage with the Nordstrom sale!

    Reply
  13. Lisa says: November 5, 2014 at 9:54 pm

    Great post! Cute outfits! It is so helpful to see different ways to wear things with clothes and accessories most of us already own. Well done.

    Reply
    • hisugarplum says: November 6, 2014 at 3:42 pm

      Yay — I'm so thrilled you like it! That is my goal…to give you ideas of how to pair items in your closet in new and fresh ways! I try to get as much mileage out of all my pieces as humanly possible!

      Reply
  14. Jenny says: November 5, 2014 at 10:04 pm

    You are always just so cute! And I am jealous of your cold 60 degree temps. That would be heavenly right about now! 😉

    Reply
  15. Shelley | Crazy Wonderful says: November 6, 2014 at 12:24 pm

    I love every single look! I need to go shopping.

    Reply
  16. [email protected] says: November 6, 2014 at 5:36 pm

    These outfits are all so adorable! I can never get enough of boots right now. I've got 5 pairs and want more!

    Reply
  17. Sheaffer {Pinterest Told Me To} says: November 7, 2014 at 1:40 am

    I think your hair looks FAB! And that coat is crazy cute. Loved seeing all of the different ways you styled the boots! And listen….It's a good think I like you a lot, or I might consider you too cute to be friends with.

    Reply
  18. Becca | In My Humble Opinion says: November 7, 2014 at 3:34 pm

    The look with the gingham and the cream sweater is lovely! I really need to go get me some new boots! Thanks for sharing all these great looks 🙂

    Reply
  19. Anonymous says: November 13, 2014 at 9:46 pm

    I love that white cable turtleneck sweater. It's a little different that the Halogen one you have linked. Is yours the same from Nordstroms? It looks great on you and love your little ponytail. So cute!

    Meg

    Reply

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