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PortraitFlip LLC – Handmade Custom Portraits

Custom Anniversary Paintings From Photo

Hand-painted anniversary portraits in oil, watercolor & charcoal by real artists. Starting at $89.

Paint My Portrait

Starting at $89

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Pay Only 20%

In Advance

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Approving Painting

Oil painting of couple embracing near Eiffel Tower

Explore Our Anniversary Painting Mediums

A successful wedding requires falling in love multiple times. Maybe that’s why every anniversary gets its own quiet ritual of remembering.

Turn your wedding photo into a hand-painted anniversary painting instead of leaving it in an album nobody opens. Oil, watercolor, or charcoal, painted by a real artist, it’s the kind of thing you actually hang on a wall.

Every anniversary year has its own material: paper for the first, silver for the 25th, gold for the 50th. A hand-painted portrait works for any of them, and unlike most anniversary gifts, it doesn’t wear out or go out of style.

Parents count too. A hand-painted portrait for their 25th, 40th, or 50th says more than another frame or a card, especially next to what usually turns up on an anniversary gift list.

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 a couple holding anniversary portraits while sitting on a couch
Picture of a woman holding her dog in her arms with same pose in portrait hanging on the wall
Picture of a woman sitting on a couch holding a portrait that shows a man with a dog sitting in on a wood
Picture of an old man and woman sitting on couch with anniversary portraits in between that show them sitting on a rock

What Our Customers Say

Erin Rench

I couldn’t be happier with the PortraitFlip I received. It was a gift and is absolutely perfect. I will definitely be using your services again.

Erin Rench

California, United States

Carolynn L.

I got a watercolor painting for my husband, but it was switched with an acrylic painting. An excellent medium for couple portraits. Would recommend them!

Carolynn L.

Texas, United States

Andrew Lindcomn

PortraitFlip did an amazing job. The painting was so lifelike that I ordered an oil-based painting of us for our anniversary. She loved it!!

Andrew Lindcomn

Tennessee, United States

Teresa Lynn Martin

Portrait Flip did an amazing job turning a photo of our deceased dogs into an oil portrait. It was a gift for my husband for our anniversary. He really loved them!!

Teresa Lynn Martin

Georgia, United States

Anniversary Oil Portraits

Anniversary portraits of a woman and a man sitting with a dog beside them
Anniversary portraits of bride and groom with their forehead stick together
Anniversary portraits where a man is kissing on woman’s forehead
Anniversary portraits of a bride and groom where the bride is holding a bouquet of flowers in her hands
Anniversary portraits where the man is behind woman and the woman is wearing pearl necklace
Anniversary portraits of a couple where the man and woman are sitting in a forest area with two dogs in front of them
Anniversary portraits of a couple where a man is sitting next to a woman
Oil painting of Indian couple in traditional attire indoors
Oil painting of man proposing to woman in garden
Oil painting of a wedding couple from photo

Anniversary Charcoal Portraits

Charcoal painting of a couple where the man’s face is close to woman’s forehead
Anniversary portraits of a couple where the woman’s arm is around man’s chest
Anniversary portraits of a man taking selfie with a woman beside him
Charcoal painting of a couple where the man is talking selfies with the woman

Anniversary Watercolor Portraits

Anniversary portraits of an old couple who are sitting on a bench
Anniversary portraits of a couple where woman’s arm is around man’s neck along with bouquet of flowers on her hand
Watercolor painting of smiling couple portrait
Watercolor painting of engaged couple kissing on colorful street
Anniversary portraits of an old couple who are placed next to each other
Couple holding hands Valentine's Day watercolor

Anniversary Colored Pencil Portraits

Anniversary portraits of a couple kissing each other
Anniversary portraits of an old couple where man’s arm is around woman’s shoulder
Anniversary portraits of a man and a woman where woman is holding a bouquet of flowers in her hands
Anniversary portraits of a couple standing next to each other

Anniversary Pencil Portraits

Charcoal drawing of an elderly couple portrait
Charcoal drawing of a couple portrait
Anniversary portraits where woman is taking selfies with a man
Black and white picture of a man and woman standing close to each other with a bouquet of flowers in woman’s hand

Anniversary Acrylic Portraits

Anniversary portraits of a couple where man’s face is on top of woman’s face and they are close to each other
Anniversary portraits where a man and a woman are kissing each other
Anniversary portraits where the woman is standing beside the man with her hands on his shoulder
Anniversary portraits where a man and a woman are holding a dog their hands
Acrylic wedding couple portrait from photo
Acrylic painting of a wedding couple from photo

Anniversary Pastel Portraits

Pastel wedding portrait painting from photo
Pastel portrait of a wedding couple from photo
Anniversary portraits where a woman is taking selfie with a man and a lake view in background
Anniversary portraits of a woman kissing man’s cheeks

Why Get Anniversary Portraits From Photos?

Rekindle a couple’s love with the gift of an anniversary portrait.

Anniversary portraits are also a wonderful way to add to your wall décor.

Want something bolder? Turn your anniversary portrait into a royal oil portrait and give your love story a cinematic feel.

We can also merge your original wedding photo with a recent one in the same frame, showing how far you’ve come since you said, “I do.”

Married on a beach, in a garden, or in your hometown church? We’ll paint that setting into the background, so the place means as much as the people in it.

Had a first dance song that meant everything? We can echo a line or its title in the piece, keeping the music part of the memory too.

What Else Do We Offer?

Every anniversary has its own story. Wanna see how we work yours into the portrait?

By Adding A Message

Is there something you never quite say out loud? Tell us how much you love their habit of talking in their sleep, or how beautiful they look every morning, and we’ll paint the message into your handmade anniversary portrait at no additional cost.

By Adding A Special Date

Pick the date that matters most. The day you met or the day you got married, and we’ll paint it into your anniversary portrait.

By Getting A Custom Royal Portrait

Every couple has a favorite screen romance. Turn your photo into a custom royal portrait and see yourself as a king and queen, hand-painted by a real artist.

Other Customizations

Want something extra? We can add a person from a different photo, change the background, or adjust clothes, hair color, and poses. Leave your requests in the “suggestion for painter” box, and we’ll do our best to deliver an anniversary portrait you love.

Frequently Asked Questions:

Custom anniversary portraits start at $89, with pricing varying by medium and size. Every portrait includes unlimited revisions and free worldwide shipping.
The best anniversary gift is something personal that reminds you of each other’s love, like a hand-painted portrait made from a photo of the two of you. It works for any year, and it hangs where you’ll see it every day.
Recreate a favorite wedding photo, or take a new one from your wedding day, a favorite trip, or at home. Any of them can become a hand-painted portrait, or we can merge your old and new photos into one.

Oil is our customers’ favorite and a natural fit for wedding photos. Charcoal and pencil give a classic black-and-white look, while watercolor and pastel are softer.

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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