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PortraitFlip LLC – Handmade Custom Portraits

Custom Retirement Paintings From Photos

A meaningful retirement gift, hand-painted from your photo by professional artists. Starting at $89.

Paint My Portrait

Starting at $89

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Worldwide

Pay Only 20%

In Advance

Rest After

Approving Painting

Oil painting of a smiling couple cheek to cheek, the man in a white cap

Explore Our Retirement Painting Mediums

Retirement means saying goodbye to years of hard work and hello to a new beginning. Cheers to all those years of learning, growing, and succeeding.

Retirement is a statement: they achieved success. Make their last day count with a custom retirement painting from their photo.

A personalized retirement gift should last long after the party. For a retiring dad, mom, boss, coworker, teacher, or nurse, a hand-painted retirement portrait is a keepsake they’ll display for years.

Retiring from service? We can paint a veteran, police officer, or firefighter in uniform and add a flag or badge at no extra cost.

Giving it from the whole team? A hand-painted portrait is a standout group gift, and everyone can chip in.

We Guarantee You Will Love Us!

  • 100% Hand-Painted Portraits
  • 24/7 Live Chat Support
  • Rated 4.8/5 on Trustpilot
  • Unlimited Free Proofing & Revisions
  • Served 25,000+ Customers
  • Free Worldwide Shipping
  • Painted by Professional Artists
  • Dedicated Support Manager
  • 100% Satisfaction Guarantee
  • 100% Money-Back Guarantee

Your portrait, hand-painted & delivered in as little as 14 days!

Video Testimonials

Our Happy Customers

Picture of an old man holding a painting that shows a close-up of dog’s face
Father's Day Paintings Happy Customer
Happy customer with their retirement painting
Retirement Painting that shows a lady standing in between a man and a woman

Compilation Portraits

Compilation picture of a man placed behind two young boys and a girl beside him is a father’s day paintings
Compilation of father’s day paintings where an old woman is standing between one young girl and boy
Father’s day paintings of a man holding a baby in his arms
Retirement Paintings where a baby is placed in the arms of a man
Compilation picture of three woman placed next to each other is a Retirement Paintings
Compilation picture where a baby boy is placed between an old man and woman

What Our Customers Say

Lucas Smith

Surprising my father with a retirement painting of him as a younger man sailing was one of the best ideas. Cheers to PortraitFlip for making his day!

Lucas Smith

Ohio, United States

Ethan Clark

I had never given my father any gifts until he retired. Thanks to my friend, who introduced me to PortraitFlip. My father just loved this retirement painting.

Ethan Clark

New York, United States

Emma

My parents were professors. They retired the same day, which was cute for a couple. On their retirement day, I surprised them with a retirement painting. Their reaction was priceless!

Emma

Tennessee, United States

Retirement Oil Portraits

Picture of a young lady near the chest of an old man is converted into father’s day paintings
Father’s day paintings where an old man is sitting with a man
Father's day paintings of an old man in a white cowboy hat on his head
Father’s day paintings where an old man is sitting next to a young girl
Retirement Paintings where an old man is standing beside a man holding a basketball
Retirement oil portrait
Grandmother hugging grandchildren retirement oil painting
Grandfather with grandchildren retirement oil painting

Retirement Charcoal Portraits

Charcoal painting of a young boy and an old man standing next to each other
Retirement Painting where the woman is leaning on the man’s shoulder
Father’s day paintings where an old man is sitting with a young girl beside him
Charcoal painting that shows a baby placed in between a woman and an old man

Retirement Watercolor Portraits

Father’s day paintings of two men standing next to each other
Father’s day paintings where two men wearing a bow tie are placed next to each other
Picture of an old man with a baby baby girl in her arms
Retirement watercolor portrait
Elderly couple with grandson retirement watercolor painting
Grandparents and grandson retirement watercolor painting

Retirement Colored Pencil Portraits

Grandfather holding grandson retirement colored pencil painting
Retirement Paintings of an old woman holding a baby in her arms
Compilation picture, where a man is placed beside the woman
Retirement colored pencil portrait

Retirement Pencil Portraits

Black and white picture of an old man and a young boy placed next to each other
Retirement Paintings where a man and a teenage boy are placed next to each other
Picture of a two men placed behind two young boys
Black and white picture of an old man with a baby is converted into father’s day paintings
Retirement Painting that shows a man and a woman standing close together
Retirement pencil portrait

Retirement Acrylic Portraits

Acrylic painting of a man sitting beside an old man
Retirement Paintings that show an old couple standing next to each other
Father's day paintings of a man sitting on a couch in a check suit
Father's day paintings where a man is playing an electric guitar
Father's day paintings of a bride whose hand is on the chest of an old man
Father's day paintings of a man sitting behind two woman and a young man in front
Retirement Paintings of a couple facing each other
Compilation of pictures which show a woman placed between a lady and a man holding a baby in her arms

Retirement Pastel Portraits

Father’s day paintings of a baby girl sitting between two men
Father’s day paintings where an old man and a man are sitting next to each other
Father’s day paintings where a man with black hat is standing behind two boys in front of him
Father’s day paintings where an old man is next to a baby with a soft toy

Why Get A Retirement Painting?

A retirement painting honors the career they built and points to what comes next, like the world trip that has been on their bucket list for years.

Some retirements get a big party; others get a quiet goodbye. A custom retirement gift like a painting marks the career either way.

Retiring means leaving the people they worked beside for years. A retirement painting made from a last-day team photo keeps the whole crew with them.

A retirement painting can include family who cannot be at the celebration, including a lost parent they wish could see this day.

Retirement often means more time with the grandkids. A retirement portrait of them together celebrates the years ahead.

Many people set a creative passion aside while they worked. A retirement painting can inspire them to pick up a brush or pencil and try something new.

How To Personalize A Retirement Painting?

A few small details make a retirement painting feel made just for them. Add a note with your photos, and our artists will work it into the painting.

Paint Them In Their Work Outfit

Let the painting show the career they are proud of. Ask for the scrubs, suit, apron, or hard hat they wore every day, or add a short note about what a great coworker they were. Their initials can go in too, as a finishing touch.

Add A Missing Loved One

Some of the people they love most can’t be at the celebration. Send us a separate photo of each one, and our artists will place them beside the retiree in the finished portrait.

It’s Never Too Late

Retired last month or years ago, they still deserve a proper send-off. Surprise a parent, mentor, or favorite teacher with a retirement painting and bring back their big day.

Frequently Asked Questions

Custom retirement portraits start at $89, with pricing varying by medium, size, and the number of people in the painting. Acrylic paintings start at $149.

A good retirement gift marks the career and looks ahead to what comes next. A hand-painted retirement portrait does both, which makes it a thoughtful gift for a coworker, boss, teacher, or parent.
Yes. You can add details like a bouquet, an appreciation trophy, or their work outfit. Mention it in your note with the photos, and our artists will work it into the portrait.

Place your order with our compilation portrait service. Upload a photo of the retiree and a separate photo of each family member you want to add. Use your note to tell us how you would like everyone arranged.

Yes. We offer discounts on bulk orders. Email us the number of paintings you need, and we will work out a discount for you. Each employee gets their own portrait, so send a separate photo and note for each one.

How It Works?

Upload your photo to place your order

Place Your Order

Choose your medium and size, upload your photo, and get started with 20% upfront.

Artist starts painting your portrait

Painting Begins

A professional artist hand-paints your portrait, backed by 24×7 support.

Preview your painting and request revisions

Preview & Revise

Approve your preview, or request unlimited free revisions until it's perfect.

Framed portrait delivered to your door

Framed & Shipped

We pack it carefully and deliver it to your door in as little as 14 days.

Paint My Portrait

100% Money Back Guarantee + Free Shipping Worldwide! Pay Only 20% In Advance. The Rest Only After Approving Your Painting!

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