This is the first post in my “20 ways series”, starting off with How to Style OTK Boots 20 Ways! This one came highly requested so I decided to do this one first since it’s still cold outside and OTK boots are in full swing! Each month I will be styling an item from my closet that is staple and showing you 20 ways to wear it. For today’s OTK boots, I am actually styling all four pairs of OTK boots that I own. Two I purchased over the past few days and two of them are ones I actually received through a boutique that I worked with. I am VERY impressed with all four of these boots and cannot wait to style them 20 ways for you! 

How to Style OTK Boots 20 Ways

ONE

Simple outfit that would be perfect for work or a day of errands!

Long Turtleneck Tunic | Zella High Rise Leggings | Flat OTK Boots | 

TWO

This look is one of my favorites because of it’s simplicity and ability to be worn pretty much year round except for the dead of summer 😉 

Long Sleeve Tee | White Distressed Denim | Heel OTK Boot – these boots fit like a GLOVE. I am very impressed with their quality and love them!

THREE

Layer with a puffer vest!

Turtleneck Sweater | Puffer Vest | Denim | Heel OTK Boots 

FOUR

Oversized, off the shoulder sweater always looks adorable with a little OTK action!

Off the Shoulder Sweater | Denim | Heel OTK Boots | 

FIVE

Basic white tee with flat OTK boots is the perfect outfit for running around with the kids all day!

Tee | Denim | Flat OTK Boots 

SIX

Belted this dress so that it broke up with boots and the hemline!

Turtleneck Dress | Heel OTK BOOKS 

SEVEN

Belt a cape for a unique look!

Turtleneck Sweater |  Plaid Cape | Zella High Rise Leggings |Heel OTK boots 

EIGHT

I am IN LOVE with this cute denim skirt. I’m not typically a skirt type of gal but love this skirt for spring/summer transition!

Cozy Sweater |Denim Skirt |Heel OTK Boots |

NINE

Layer with a long flannel!

Flannel |  White T | Faux Leather Leggings | Heel OTK Boots | 

TEN

Basic tee with black faux leather is a great statement while still playing it cool 🙂 

Black Hat |Green Tunic |Faux Leather Leggings | Heel OTK Boots 

ELVEN

Layer with a draped waterfall vest! 

White Long Sleeve T |Vest |Faux Leather Leggings | Heel OTK Boots 

TWELVE

A work option – layer with a longer white collared shirt underneath for butt coverage! 

Leopard Sweater |White Button Up |Faux Leather Leggings | Heel OTK Boots 

THIRTEEN

One of my favorite options for a date night or going out with the girls! Edgy & pulled together!

Suede Moto Jacket |Black Long Sleeve | Faux Leather Leggings | Heel OTK Boots

FOURTEEN

Nothing better than a classic striped turtleneck layered with a cozy long cardigan!

Striped Turtleneck | Belt | Denim | Cardigan | Heel OTK Boots 

FIFTEEN

Another classic striped tee but this time styled with a great leather jacket!

Striped Long Sleeve |Leather Moto Jacket | Denim | Heel OTK Boots 

SIXTEEN

For the days when you don’t wanna wash your mane 😉 

Basic Long Sleeve T | Denim | Baseball Cap | Heel OTK Boots 

SEVENTEEN 

Another off the shoulder option but with a longer hemline!

Off the Shoulder Sweater | White Denim | Flat OTK Boots 

EIGHTEEN

Don’t know what it is about cognac paired with white but I loooooooove it.

Hat | Mine is sold out but I linked a similar option | Chunky Turtleneck Sweater | White Denim |Heel OTK Boots 

NINETEEN

Another longer cardigan option

Basic Long Sleeve T | Cardigan | Green Denim | Heel OTK Boots 

TWENTY

Edgy, going out look! Since the leopard tee is a bit shorter, I layered it with a longer U hem tee underneath to get that length in the front and back!

Leopard Print T |Black Layer T |Faux Leather Leggings | Heel OTK Boots