Fall Transition | Knee Boots & Moto Jacket

Cheers to Friday, friends, and the weekend ahead! My sister is in town with my darling nephew, so we’re meeting them at the lake to soak up that sweet baby smell! We  had a glimpse of Fall in the last weeks, but the heat is back in full force this weekend, so it will be fun to see him experience swimming for the first time. Assuming I even get near him…Little Miss usually keeps him all to herself!

Today we’re wrapping up the latest Five Ways Series, all about transitioning your wardrobe to Fall. When creating outfits for a Five Ways series, my goal is to give you options for a little bit of everything…work, weekend, and date night. Today’s style shows the power of a good knee boot, and its ability to sass things up for day and night!

Ruffle-Trim Top (40% off!) | Mid-Rise Jeans | Knee Boots | BagSimilar Sunglasses | Earrings | Lipstick in ‘Punch’

Remember yesterday when we talked about covering your arms or legs for work wear? The same theory applies to pretty much any Fall transition outfit…here I took a favorite Summer blouse, and made it Fall-worthy with rich, suede boots and dark rinse jeans.

This shirt had me at ruffles, and I’ve worn it with everything from shorts to skirts, and now jeans and slacks. It’s a crisp poplin cotton with a low back, but still works with a traditional bra (I swear by this one).

Fit Tip: The top is true to size, I’m wearing a 0. The length is great for tucking in, or wearing out.

Ruffle-Trim Top (40% off!) | Mid-Rise Jeans | BagLipstick in ‘Punch’ | Watch | Bracelet | Necklace

You could add a pop of color with this bag, but I kept things neutral for this one, and let the ruffles and boots make all the statement.

Ruffle-Trim Top (40% off!) | Mid-Rise Jeans | Knee Boots | BagSimilar Sunglasses | Earrings | Lipstick in ‘Punch’ | Watch | Bracelet | Necklace

When it cools off even more, or you want to take this get-up on the town, just add a moto jacket. I fell for this jacket last year (see it worn here), and I’m thrilled to see it back, and in new colors. This one is a great option, too. I love the laid-back vibe moto jackets bring to an outfit, but prefer ones with a feminine touch so they’re more edgy than biker. Does that make sense?

Sidenote: I’ll have you know I had a Ross moment when it came time to take this jacket off! #Friends Let’s just say it wasn’t exactly chilly when I shot this look!

Ruffle-Trim Top |Moto Jacket (suede option) | Mid-Rise Jeans | Knee Boots | Leopard Clutch | Similar Sunglasses | Earrings | Necklace | Lipstick in ‘Punch’

Swapping the bag for a punchy clutch makes it even more date night ready.

Ruffle-Trim Top (40% off!) |Moto Jacket (suede option) | Mid-Rise JeansLeopard Clutch | Similar Sunglasses | Earrings | Lipstick in ‘Punch’ | Necklace

I lucked out and grabbed these gorgeous boots during the Nordstrom Anniversary Sale, and can hardly wait to pair them with all my jeans, skirts and dresses this Fall and Winter. They’re even sleek enough for pencil skirts! The caramel shade is so rich and will go with virtually everything, and the sturdy heel makes them comfy for walking. They’re definitely an investment piece (for me anyway), but they are timeless and I’ll wear them for years!

Fit Tip: They are true to size, but if you have really wide calves, they may not be for you. I have fairly ‘athletic’ calves, and the shaft is a tight fit…but they’re already loosening up after a couple of wears.

Knee Boots

Ruffle-Trim TopMoto Jacket (suede option) | Mid-Rise Jeans | Knee Boots | Leopard Clutch | Similar Sunglasses | Earrings | Necklace | Lipstick in ‘Punch’

Did you have a favorite from the Transitioning to Fall series this week (click the link below each pic for the full post)?

Fall Transition | Camel & Black

Fall Transition | Gray & White (featuring these must-have booties under $100!)

Fall Transition | Tiered Ruffles

Fall Transition | Peplum & Camo (adore this peplum tee!)

how to transition to fall

I hope you’ve enjoyed this series as much as I loved creating it, and you found some inspiration for this new season. Which look was your favorite of the week? What would you like to see featured in the next Five Ways series?! Happy weekend, lovebugs!

{Shop Today’s Fall Transition Style}


*Photos by the darling and talented Mary Summers. This post is created in collaboration with Nordstrom, but all styles, opinions and pre-Fall heatstrokes are my own. Thank you for supporting Hi Sugarplum sponsors!*


Leave a Comment


  1. Love the minimal bag! Really puts the outfit in focus and highlights the colours.
    Have a great weekend. 🙂

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 9.15.17 Reply
  2. Shay Shull wrote:

    I need every single thing in that first outfit…from the earrings down to the boots.

    Posted 9.15.17 Reply
  3. Jennifer wrote:

    I love them all but I think my favorite is the dress! I love dresses and the way you transitioned this one into fall is genius! 🙂

    Posted 9.15.17 Reply
  4. Sandy wrote:

    Once in a blue moon, I stop someone on the street and say to them “you look so cool & pulled together”. It would be this look, knee boots & moto jacket. That shade of demin really makes this look sing! I’m salivating over those boots!
    I love all the looks, no real favorite. And is there anything better than babies and beaches? I think not! Thanx for sharing.

    Posted 9.15.17 Reply
  5. Celine wrote:

    Love all of these looks, can’t wait to try some of them! I’m getting those turquoise- colored earrings ASAP! As always, thank you for the inspiration….looking forward to what’s next…

    Posted 9.15.17 Reply
  6. Nailed it again! Love the ruffle top- simple but special at the same time. I think my favorite outfit is the one you wore with the camo jacket. You have the best style!

    Posted 9.15.17 Reply
    • Cassie wrote:

      Thank you so much, Britney!! Happy weekend! xo

      Posted 9.15.17 Reply
  7. Janet wrote:

    Do you have anything showing an over the knee boot, style, what to wear with it?

    Posted 9.15.17 Reply
  8. Kendall wrote:

    I love this look! Adding it to my Fall wardrobe inspiration Pinterest board 🙂

    Posted 9.22.17 Reply