Dillard Street Barber Shop

Great MENS haircut. Jack knows what he’s doing and you don’t have to tell him how to do it. He’s fast and has a great personality in the process. Not many traditional barber shops with skilled barbers any more. Enjoy this one while it lasts.

Jack is a great barber. His shop is a throwback to barber shops of old. Bring cash (no credit cards accepted) and a good story. Jack will entertain you with entertaining conversation, but don’t make him carry the load unassisted.

First visit today and I will be going back regularly now. Jack is a super nice guy and knows his craft well. He tried something a little different than I normally do and it was great. Highly recommend him! 👍

Best Barber and Best Haircut Period. Has to be in the top ten Nationwide. Jack is truly a Master at his craft. No other barber in New York, Boston, Miami or Los Angeles ever came close to scratching the dirt at the bottom of Jack's shoes. I have often been tempted to hop on a plane and fly to this hidden gem in Winter Garden for the best haircut of my life. It would be worth it.

Ok... so this is a location that is totally worth visiting. Jack is an amazing and friendly barber and gives a great flattop. Gentlemen, this is the place to go for old-school and masculine haircuts. You will need to pay $20.00 for a flattop but the cut is worth it. Also, he had his ow parking lot in Downtown Winter Garden, a plus. Thanks Jack.