#1 In Poughkeepsie

For a Timeless Look

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About Us

Timeless Barbershop, founded in 2015, is a locally owned, family-run barbershop in Poughkeepsie, NY, led by the dynamic barbering couple Jason and Kara. More than just a place for haircuts, we create an experience rooted in precision, style, and genuine care. Located in the heart of the Hudson Valley, we take pride in delivering expert haircuts and classic barbering services with meticulous attention to detail. Whether you’re looking for a blurry fade, a crisp beard trim, or a traditional straight-razor shave, we provide a welcoming atmosphere where every client leaves looking sharp and feeling their best. Come visit Timeless Barbershop in Poughkeepsie and experience the difference of a barbershop that values craftsmanship, community, and top-tier service.

Explore services Meet Charlie
since 2015

Our Team

Jason

Barber

Kara

Barber

Tim

Barber

Bailey

Apprentice Barber

Meet Charlie

Meet Charlie, the heart and soul of our barbershop! Our four-legged friend greets every guest with a wagging tail and a warm welcome. Whether he’s lounging in his favorite sunny spot, keeping an eye on the action, or trying to rope you into playtime, Charlie makes every visit just a little brighter.

Known for his chill but playful demeanor and uncanny ability to sense when someone needs a little extra love, Charlie has become everyone’s favorite co-worker and companion. Stop by for a haircut, stay for the puppy snuggles—Charlie’s always here to make sure you leave with a smile.

Our Services

Haircut
Starting From $30
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Beard Trim
Starting from $5
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Wash, Cut, Blowdry
Starting from $40
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Add-Ons
Starting from $5
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Prices Apprentice / Master

Regular
  • Haircut
    $30/35

    A thorough consultation followed by a custom, detailed cut to fit your lifestyle.

  • Beard Trim
    $5/10

    Clean lines and expert grooming to pull it all together. Request the straight razor line up to get your sharpest look

  • Wash, Cut, Blowdry
    $40/45

    Includes a refreshing wash, precision cut, and sleek blow-dry.

Add-Ons
  • Fade
    $5

    A seamless fade for sharp definition.

  • Camo
    $20

    Conceal grays or uneven tones for a natural look.

  • Hot Towel Shave
    $30

    Relax with a hot towel and a close, precise shave..

  • Wash, Cut, Blowdry (Long Hair)
    $10

    Perfect for longer hair, with a wash, cut, and polished blow-dry.

What Others Said

I got married up near poughkeepsie a few weeks ago, and needed to get cleaned up for the big day. Luckily, Jason had a cancellation and was able to fit me in on short notice. My hair (or lack thereof, these days) is not that complicated, but Jason was awesome to work with. He listened to what I wanted for both my hair + beard, and I couldn't have been happier with how it turned out. Jack Ferris
Jason, gave me a good haircut 💈💈💈💈💈. I liked my haircut and my Mom, liked it too. It was my first time going here. The place is clean and not far from Vassar College. Robert Hufnagel
My experience with Kara is always so amazing! She has a lot of knowledge when it comes to hair and is always sharing new tips and products with me to keep my hair healthy! I highly recommend coming to Kara, you will not regret it! Alexandra Patricia
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Years in Business

5 Star Reviews

Satisfied Customers

Please Give us at Least 24 Hours to Confirm Your Appointment

Fill out the below form to request your appointment. We will check our availability and get back to you with a confirmation or contact you to set up a different time as soon as possible. This form does not confirm your appointment. If you need an appointment immediately, give us a call at 845-204-9944. Thank You!

Phone appointment

(845) 204-9944
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