The paddock boot has long stood the test of time, regardless of season, age or riding ability. They are a constant in every equestrian’s closet, trunk or tack room.

But if I’m going to invest in any piece of apparel, it has to serve not only my #ROOTD but also make the transition to #OOTD or better yet, my #OOTN.

These Ovation Paddock Boots do just the trick.

I’m wearing them at 8 am while I muck stalls. The Cambrelle wicking material keeps my feet dry (because let’s face it, I’ll probably spill at least two water buckets as I’m unhooking and cleaning them) and the ComforLast cushion insole is super comfortable. I’m on my feet all day, so this is a must-have for my barn footwear.

My first ride is at 9:30 am, so I just zip on my favorite pair of half chaps over my paddock boots, and I am good to go!

Dublin Evolution Side Zip Half Chaps, $63.59 (Orig. $109.99)

After my rides are done around 1 pm, I keep these shoes on for afternoon barn chores. These boots have a wear-resistant outsole, which is great for me because I have to walk the horses quite a ways to their turnouts in the afternoons, and it means these boots will LAST.

My day is done at 5 pm, and after a quick shower (super lucky to have one in our barn!), I pull on a pair of jeans, cuff the bottoms, throw my paddock boots back on and head straight to an outdoor happy hour where I can finally catch-up with friends after a year of COVID!

The day is done, the night is young, and my paddock boots have transitioned through every outfit change.

How do you style yours?