West & Kennedy Barbershop

Update 10/2025 - Still the best shop in Winter Park. Caleb, Kensil, Ralph, and Reggie are masters at their craft. Any hair type any style, you are covered here. It is rare to find a shop that caters to everyone, but here they really do. Professional consistent quality! Thats what matters. If you're looking for a quality cut with attention to detail and excellent service look no further. You won't find a shop that personally caters to each customer. No matter your hairstyle or type of hair Reggie and Ralph can deliver and up your style points. I've been to shops from London to New York and West and Kennedy is hands down the best I've been. Highly recommend!!

Kensil at West & Kennedy is hands down the best barber this side of the Mason-Dixon! Every cut is sharp, clean, and exactly on point — he’s my go-to every time. Don’t get me wrong, Reggie, Caleb, and Ray are also great at what they do, but Kensil is my guy. The shop itself has an incredible atmosphere — it’s inspirational, motivating, and always filled with positive energy. Every visit feels like more than just a haircut; I leave feeling confident, refreshed, and ready to take on the world. If you’re looking for a barber who truly cares about his craft and a shop with great vibes, this is the spot. Highly recommend!

Made an appointment and paid $15 deposit. Received a message that they were going to switch me to another barber - fine. Barber was 20 minutes late for appointment and then charged me $45. They not only charged the $15 deposit again, but then charged $10 above the quoted price. In discussions with the owner, they said this was because they switched me to another barber but failed to disclose there would be a higher price. I would not have gone if I knew there was going to be a bait and switch involved. Owner also subtly made it sound like I was at fault here. Ended up disputing the charges on the credit card after no further resolution attempts.

Love this barbershop! The whole team seems like family. It's a great diverse body of clients of all ages and races. Makes you feel good and light hearted Everytime you go. Easy listening jazz, great conversation and great vibes. I love my neighborhood barbershop. It's also on one of the most beautiful blocks in Winter Park with great restaurants so you can grab a bite to eat or cocktails after and let your lady enjoy the shops or salons on the block while you get a clean cut.

I recently visited Pedro for a haircut and beard trim, and I couldn’t be happier with the results! Pedro’s attention to detail is impeccable. He took the time to understand the style I was looking for and made sure every cut was precise. The beard trim was especially impressive – clean, sharp, and exactly how I wanted it. His professionalism and personality made the experience even better. If you’re looking for someone who knows their craft and delivers top-notch service, Pedro is the barber to go to. Highly recommend!