Small Business Spotlight: Personally Preppy

In the words of Lauren from She Moved to Texas: MONOGRAM ALL THE THINGS. Monograms are awesome in so many ways. Not only are they really pretty and stylish, but for those of us who board we understand that personalization can help prevent things from growing legs and wandering away. Put down your Sharpie, people – there is now a better way.

My featured business this week for the Small Business Spotlight series is Personally Preppy. If you have Instagram you have probably seen one of their fabulous helmet monograms by now, which have absolutely blown up in popularity over the last few months. They also offer glove monograms, breeches monograms, monogrammed whips, cell phone cases, etc etc. Just about everything a monogram lover could possibly dream up. The best part is that everything is very affordable – you can go crazy and stick a monogram on everything without breaking the bank. See their full line-up on their Etsy store:


As soon as I first saw their helmet monogram I knew I absolutely had to have it. I opted for black since it would be more subtle on my show helmet, but still a really cute and fun way to personalize it. As soon as I had that, I ordered a monogram for one pair of my show breeches and my show gloves. Last week I ordered a light blue monogram for my “junker” schooling helmet. Because… awesome.



You aren’t limited to only the things you see in their store. If you can dream it, they can probably create it. Custom orders are no problem. In fact, I am getting ready to submit my fourth (addiction much?) order, for a custom heat transfer to go on a new fly bonnet. We won’t talk about how many fly bonnets I have either.

If you’ve read any of my Small Business Spotlights by now, here’s the fun section you’re expecting: words from the business owners!

1) When did you start this business?
Personally Preppy opened their online Etsy shop in April of 2014.


2) How many employees are there in your company?
We have about 5 employees, and a few brand ambassadors. Tate & Kir are very hands on with each order, but attribute our success to a hard work ethic, and a passion for horses & riders. As riders, Tate & Kir love supporting riders around the world, who also share the same passion for the sport and the animals.


3) Where did the idea for the business come from?
While competing at an IHSA show as Captain of the Salve Regina Equestrian Team, Kir recognized that the girl’s helmets, crops, gloves, and saddle pads were constantly confused and sometimes lost. As an avid “Prepsters” and Equestrians we knew monograms was the solution! Later that night, Tate and Kir started Personally Preppy. They said “It was a big risk starting a company in college but with hard work and perseverance Personally Preppy was born!”


4) What is your background in horses?
Tate & Kir, best friends, and sisters began Personally Preppy while Tate was pursuing her MBA and while Kirsten was a freshman, both at Salve Regina University.  While growing up in Westchester, NY we began horseback riding at a young age, and got hooked into the horse show world after our first Walk-Trot class!  Our parents, both successful entrepreneurs, consistently encourage us to find an idea, and be strong business women. Together, as a team, Tate & Kir ran pony camp to help pay for their horse shows. While working in the industry, and being avid horse show girls, we recognized that everyone has similar clothes, and equipment in the horse world. We agreed that monogramming would be a fun, yet classic way to let our preppy style shine in the ring. Today, Kir and Tate are thrilled with the consistent growth of the company, and continue to add new, quality products with a strong attention to customer satisfaction.


5) Any interesting notes about yourself, your business or your products that you would like for people to know?
We are a sister run company, we love working together as best friends, and business partners. We support girl power, and the power of hard work. We love supporting riders around the world who have a love for their horses as well as a love for equestrian style.
We want to thank our Mom, (our creative consultant) our Dad (our number 1 fan)  and our Brother Ricky (our production assistant) for believing in us, being patient while we hog the dinner table conversation with horses and always encouraging us to chase our dreams.




There is a lot to love about Personally Preppy. Style, practicality, affordability and fun. All of that while supporting a small business at the same time – doesn’t get much better. Find them on Instagram at personallypreppy to stay up to date on all their cool new stuff. Thanks Personally Preppy for all of your great products thus far, and the ones to come in the future!


17 thoughts on “Small Business Spotlight: Personally Preppy

  1. Have you done your fly bonnet yet? Does it stick well to the crochet? That is something that didn’t even cross my mind, but I just might have to steal the idea!


    1. I actually just got a bonnet that has a little patch of fabric on it, so that’s where I’m gonna do the heat transfer. I don’t think I’d bother trying it over just the crochet part, it stretches too much.


  2. Ok, another question. Do the heat transfers do well in the wash for saddle pads and such? Was thinking this might be a fun way to monogram my saddle pad instead of doing embroidery.


    1. I’ll be able to answer that better in a month or so. Before yesterday the only heat transfers I had were on my show breeches, so they’ve only been washed once since I put them on. We’ll see how the one on the saddle pads holds up. I’m not expecting a super long life span but we’ll see what happens.


        1. The ones on my horse’s boots got annihilated (not surprising). The glove ones and helmet ones have lasted well, the breeches not so much but I didn’t apply it correctly either, so I can’t say that’s their fault. I will say that PP orders started taking forever to receive when they exploded in popularity, so I ordered more monograms from elsewhere.


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