3 Super Cute Winter Over the Knee Boots Outfit Ideas

You need these boots. Just sayin’.

This post may contain affiliate links, which means we may receive a commission if you purchase through our links. Please read our full disclosure here.

The Fabulous Find of the Week column brings you a new style steal weekly that will both keep some cash in your wallet and keep you looking, well, fabulous.

When I think of winter, the first things that pop into my head are boots. Snow boots, long boots, short boots, (faux) leather boots, suede boots . . . boots. We’ve already talked about the best boots for fall, but what about the perfect winter boot? No worries, I’ve got you covered. 

For this week’s cheap steal, I spotted these insanely cheap + stylin’ black over-the-knee boots that will match quite literally everything in your closet. They’re classy and easy to dress up, but because they don’t have high heels, you can wear them casually too and won’t hurt your feet in the process (win-win). 

So, if you need a pair of cute boots to carry you through the remainder of fall and the whole of winter, these are the shoes for you. Oh, and did I mention they’re $19.99? Yeah, steal.

Keep scrollin’ for 3 over the knee boots outfits, and by the end of this article, go ahead and order a pair for yourself. Treat yo’self. 

Over-the-Knee Boots Look 1: A Full Day of Class + Errands

Over-the-knee boots outfit with burgundy accents.

Products:

Alright ladies, over-the-knee boots do not just have to go over leggings and tights! If you get a nice jegging/skinny jean, these boots complement them perfectly. With that said, grab your favorite pair of classic skinny jeans, and a cozy, chunky burgundy sweater

A plaid poncho comes next and layers over the sweater wonderfully. It adds a bit of pizazz and a good amount of warmth to the look. A super cute burgundy beret and a simple, personalized gold bracelet are the perfect complementary accessories. Finally, pack all your stuff in this classy black tote. Love it. 

Over-the-Knee Boots Look 2: Did Someone Say Date Night?

Over-the-knee boots outfit with red dress.

Products:

Our next look is the typical over-the-knee boots + tights outfit (hey, it’s still good to stick to the basics). Pair them with this adorable red lacey dress for a bit of Christmasy/holiday spunk, and sheer black tights. A slick pony or bun suits this look well. 

For accessories, add stylish, dainty pearls: Pearl-covered hoop earrings and a gorgeous pearl headband should do the trick. Carry your phone and lipstick in this heart-shaped crossbody, too. Finally, swipe a bit of shimmery highlighter on your cheekbones for some extra glitz. Ooh la la. 

Over-the-Knee Boots Look 3: Prepster

Over-the-knee boots outfit: preppy school girl-esque.

Products:

This third look boasts a preppy, spunky, schoolgirl vibe and I’m DIGGIN’ it. Pair your boots with this chic navy plaid skirt and wintery emerald chunky sweater. Slip on a black velvet pearl choker to add a bit of edge to this preppy look.

Straighten your locks and throw them up into a loose pony with these ’80s-inspired satin scrunchies. (I’m obSESSEd with scrunchies right now.) Carry your books and laptop in a faux leather backpack. The final step is to swipe on some burgundy matte lipstick and you are set. Smart and beautiful. 

Winter Over the Knee Boot Outfit Tips and Recommendations

Over-the-knee boots are a stylish and versatile winter staple, and here are some tips and recommendations to help you rock them all season long:

Consider the Boot:

  • Material: Leather boots are classic and chic, while suede is softer and more casual. For extra warmth, choose boots with a lining or fur trim.
  • Heel Height: Stilettos are great for going out, while block heels are more comfortable and practical. Flat boots are great for everyday wear.
  • Color: Black is timeless, but brown, gray, and burgundy are also popular choices. If you want something a little less expected, try red, blue, or even metallic boots.

Styling Tips:

  • Balance Proportions: Over-the-knee boots are naturally eye-catching, so keep the rest of your outfit relatively simple. Avoid wearing anything too bulky or overwhelming on top.
  • Layering is Key: Tights or leggings are essential for warmth and can add pops of color or pattern to your ‘fit. Layer sweaters, turtlenecks, or dresses over tights for a cozy look.
  • Don’t Shy Away from Dresses: Over-the-knee boots look great with mini, midi, and even maxi dresses. Just make sure the hemline falls above or below the top of the boots.
  • Accessorize Wisely: Keep jewelry delicate and avoid chunky scarves or bags that might compete with the boots. A statement belt can cinch your waist and add definition.

Outfit Ideas:

  • Classic Chic: Pair black leather boots with straight leg jeans, a white turtleneck, and a black blazer for a polished look.
  • Cozy Casual: Wear brown suede boots with opaque tights, a chunky knit sweater, and a faux fur vest for a comfy and stylish ensemble.
  • Cool and Edgy: Rock red leather boots with a leather mini skirt, a graphic tee, and a moto jacket.
  • Winter Wonderland: Opt for gray suede boots with a snowflake-patterned sweater, a faux fur stole, and white jeans for a cute and girly winter look.

Bonus Tip: Don’t be afraid to experiment and have fun with your over-the-knee boots! They can be dressed up or down, and there are endless possibilities for cute outfits.

How does this Fab Find suit you?

Will you be buying some over-the-knee boots this winter? What are your favorite boots? Do you like these looks? Please let me know. 🙂

Leave a Comment