Collecting: Vintage Portrait Oil Paintings

There is something magical about original vintage artwork. They’re created from the imaginations and carefully honed skills of an artist’s hand, are completely one-of-a-kind, and have an energy and presence that no other decor object can have. Portraits have yet another layer of magic - the mystery of the model’s identity. Bringing a vintage portrait painting into your home is almost like adopting a new member of the family - an instant ancestor! They’re one of my favorite things to collect so I thought I’d share what I look for and where to find them, plus a beautiful collection of pieces that caught my eye!

WHERE TO SOURCE VINTAGE PAINTINGS

Aside from my first choice of scouring flea markets and antique malls, my favorite online sources are Etsy, Ebay, and One King’s Lane. I search “vintage portrait” and use search filters to narrow the results. It’s worth checking back every few months because you never know when that perfect piece will show up, and it can take some time to find the right piece.

MEDIUM

All of the pieces I’ve sourced below were created with oil paint on canvas or board. Generally, paintings on stretched canvas or are worth more because they are more structurally stable than paintings on wood or paper board, which can more easily be affected by moisture and humidity changes.

ARTIST’S SIGNATURE & PROVENANCE

Really expensive, high quality pieces will almost always include a signature of the artist on the front, as well as paperwork that details its provenance, or the trail of ownership since its creation. Not all paintings will have this, however, but plenty of incredible artwork is anonymous! In fact, it can add a layer of mystery to the painting, making it more intriguing!

WHEN TO INVEST

Everybody’s budget and resources are different, so after taking into account what you can realistically afford, I find the best measure to be my intuition! If you absolutely love the artwork, if you can’t stop looking at it, if it speaks to you in some way, then I would consider it worth investing in. Fine art, in general, is considered a long term investment, so I prefer to buy paintings I know I will love for a lifetime. That includes pieces I bought for a song and the ones with a higher price point.

18 ORIGINAL VINTAGE PORTRAITS

Below, I’ve sourced a collection of beautiful vintage portraits. They range in size, age, and price. Some would be considered investment pieces while others are more affordable works. I tried my best to find a balance of subjects including men, women, different ethnicities, and people of color, who tend to be vastly under represented in art history.

The striking blue eyes and tilt of his cap draw me in. Was he an artist, sailor, or military man? We’ll never know, but it’s fun to imagine all his possible identities.

I find the portrait of this lovely Asian girl incredibly charming! It almost looks as if she’s wearing a school uniform and I can imagine this might have been painted as a graduation present.

This painting is over 120 years old! I love the muted colors and signs of age on the man’s face as well as on the canvas.

This piece is so special. It’s definitely an investment; it’s been well conserved and the beautiful rendering of dramatic light is quite unique. This would be beautiful hung in a bedroom or, if climate allows, a bathroom vanity or dressing area.

I like the texture, contrast, and warmth in this portrait. His gaze seems very contemplative and lost in thought.

This 1890 painting looks to be a study for a larger painting. I love the loose brushstrokes and the woman’s defiant gaze.

This portrait is gorgeous! The warm vibrant color is lovely against the rich skin tone. I love how the brushstrokes are very visible and yet the character of the sitter shines through.

There’s something about partially unfinished paintings that feel more approachable than finished, polished works. This was painted by a listed Soviet artist in the 1950’s.

I love the dramatic light that accents the deep wrinkles in the woman’s face. Just like photographs of older people, I adore paintings that show how beautiful aging can be.

This may be a portrait of Armin Hansen, a Calfornia artist active in the early 1900s, although the artist who painted it is unknown.

The colors in this signed mid century portrait are incredible. I’m also very fond of her beautiful gaze, short dark hair, and her chic sense of 70’s style.

Painted in the 1960’s with beautifully muted colors and shadowing. I like the unique side profile view of her delicate features and long silver grey hair.

This oil portrait has pastel oil overlays that give this painting depth and texture. It’s an unmounted, loose canvas which I think, looks great tacked to an inspiration board or wall.

This man, relaxing in the sun, was painted in the 40s. I imagine him watching the boats come into the harbor.

The oval shape of this painting adds a special element and creates more dynamic movement to a gallery wall.

I love the kind expression of this man and his gold pocket watch hanging from his vest. This would be perfect for an office, library, or study.

I can almost imagine this being my long lost great grandmother! Doesn’t she look elegant?

The curious look in her eyes seems to capture the feeling of youth. And the colors feel like summer!

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