Day to Night | Over-the-Knee Boots

Cheers to Friday, friends! I can’t thank you enough for the love on our Closet Reveal! I literally swoon every time I walk in, and feel so inspired when I’m in there. Plus, to be able to see everything at once, makes it so much easier to create new styles and combinations. Hopefully that translates to more inspiration for y’all, too. ūüėČ

I’m super excited for today’s style post, not only because I adore the outfits (can I say that about my own outfit?!), but because I had to search far and wide to find the perfect boots for them! You may recall I’ve been trying pair after pair of over-the-knee boots in previous Dressing Room Diaries, and quickly discovered they aren’t all created equal!

Some were too¬†high on the thigh (I’m not trying to be Pretty Woman over here), and others¬†too bulky around the knee (not flattering). And it seemed anything remotely affordable (because daaaaang OTK boots can be pricey!!), was poor quality and looked cheap. You can get away with cheaper materials in a bootie, but when the boot covers 60% of your leg, it’s kind of obvious!

But I pushed on, because I’m nothing if not dedicated, and found the perfect over-the-knee boot that’s not too high, not too low, has a flattering leg-hugging silhouette, and looks super expensive! Even though they’re¬†under $100 #micdrop

Update: Boots just went on sale for 40% off…only $60!

Similar Sweater | Jeans | OTK Boots
Deer Print Bag (use code SUGARPLUM10 for 10% off!) | Hat | Sunglasses
Cuff | Necklace

The trick to getting the most flattering, leg-lengthening effect, is for the boot to hit you at the slimmest part above your knee, and hug your leg all the way down. I loved this flat pair, as well, but figured the whole point of over-the-knee boots was to make a statement, so I might as well really make a statement by going with a heel. #nobodyputsbabyinacorner

Fit Tip: These boots are true to size, and have some give to accommodate different size calves and thighs. They are a bit loose around the top for me, but have no problem staying put when worn over jeans.

Similar Sweater | Jeans | OTK Boots
Deer Print Bag (use code SUGARPLUM10 for 10% off!) | Hat
Cuff | Necklace

Similar Sweater | Jeans | OTK Boots

Similar Sweater | Jeans | OTK Boots
Deer Print Bag (use code SUGARPLUM10 for 10% off!) | Hat | Sunglasses
 Cuff | Necklace | Sunglasses

Over-the-knee boots are great with dresses, too, as long as there’s at least a few inches of visible leg between the boot and dress.¬†I love how they take a simple sweater and jeans, and make it instantly so chic. Plus,¬†I kind of feel like I could take over the world when I wear them.

They’re also great for jazzing up an outfit for a night out. I’d normally pair this moto jacket and jeans¬†with a heel for evening, but the boots make it sassy and edgy! And notice how the solid black on black gives me legs for days! And believe me, that’s no easy feat on a 5’4″ frame!

Moto Jacket | Favorite Cami Tank | Black Jeans (similar) | Over the Knee Boots
Pendant Necklace | Sunglasses | Clutch | Hoop Earrings

Moto Jacket | Favorite Cami Tank | Black Jeans (similar)
Pendant Necklace | Clutch | Hoop Earrings | Spike Bracelet

This moto jacket is buttery soft, and moves like real leather (you’d never guess it’s faux!), and the warm color¬†makes it a perfect transition for Spring.

Fit Tip: The jacket runs small…even though I prefer moto jackets fitted, I still needed to size up to a small.

Moto Jacket | Favorite Cami Tank | Black Jeans (similar) | Over the Knee Boots
Pendant Necklace | Sunglasses | Clutch | Hoop Earrings

Moto Jacket | Favorite Cami Tank | Black Jeans (similar) | Over the Knee Boots
Clutch | Spike Bracelet

Are you a fan of over-the-knee boots? I hesitated for a few years, thinking perhaps they were too young for me, but now think the right pair is flattering and suitable for all ages. Happy weekend, lovebugs!

PS…As many of you noticed, I goofed several links in this week’s Dressing Room Diaries (that’s what I get for blogging at midnight!). They’ve all been updated and corrected, so make sure and check back!

{Shop Day Style}

{Shop Night Style}

Great Holiday Weekend Sales:
Nordstrom // HUGE season markdowns…including these popular booties.
Loft // 40% off everything (including the entire SignatureSoft line!)
GAP¬†//¬†Extra 25% off reduced prices with code MORE (I’m looking at you, striped popover)
Old Navy // 30% off entire order with code ENJOY (hello, ruffles!)
J.Crew // 30% off purchase with code WEEKEND (come to mama, bell sleeves)
J.Crew Factory // 50% off every single thing (cutest striped dress)
West Elm // 20% off entire purchase (love this pillow!)

*Photos by the darling & talented Mary Summers.

Leave a Comment


  1. Brittany wrote:

    These boots are amazing!!! I’m always a sucker for otk boots… Love
    How you styled them both ways! Have an awesome weekend ūüėČ

    Brittany ūüôā

    Posted 2.17.17 Reply
    • Cassie wrote:

      Thanks Brittany!! Same to you! xo

      Posted 2.17.17 Reply
  2. Miranda wrote:

    Does the blocky heel make them comfortable to wear? I’m not a heels girl so wondering before I buy!

    Posted 2.17.17 Reply
    • Cassie wrote:

      Hi Miranda! Actually, the thicker the heel, the more comfortable it is to stand for long periods of time! I didn’t find these to be too high or uncomfortable at all. Of course, if you’re on your feet all day, everything starts to hurt after awhile!! But these are worth it, imo! ūüėČ xo

      Posted 2.17.17 Reply
  3. Britney wrote:

    Super cute- love both of these looks! I’m having a hard time deciding which styling is my favorite. I like the contrast of your OTK boots with the jeans in the first look, but I also love the black pants and jacket in the second look. Both are winners!

    Posted 2.17.17 Reply
    • Cassie wrote:

      Thanks so much, Britney! Happy weekend!! xoxox

      Posted 2.17.17 Reply
  4. Amy Cotton wrote:

    Loving this look!

    Posted 2.18.17 Reply
  5. Emily wrote:

    You look amazing in these boots and give a shorter girl hope! Also, are you sure the link for your jeans in the day look is correct? The jeans you are wearing look completely different ( color, design on pocket) than the Wit and Wisdom pair it takes us to.

    Posted 2.20.17 Reply
    • Cassie wrote:

      Thanks, Emily!! My exact jeans are older, but I linked virtually the same ones, but with a darker rinse. xo

      Posted 2.21.17 Reply