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Cool & Collected: Vintage Portrait Paintings
Antique and vintage portrait paintings are the latest trend in flea market collectibles.
What’s the hottest new trend in flea market collectibles? Vintage portrait paintings. From the masterworks hung in gilded frames in the grand halls of European palaces to the intimate vignettes of our ancestors’ faces arranged on modest mantel tops, decorating with portraits has long been a way to honor our favorite people. These works usually... Keep Scrolling
Written by Kris Christensen
Photography by Bret Gum


What’s the hottest new trend in flea market collectibles? Vintage portrait paintings. From the masterworks hung in gilded frames in the grand halls of European palaces to the intimate vignettes of our ancestors’ faces arranged on modest mantel tops, decorating with portraits has long been a way to honor our favorite people. These works usually depict family members and close friends or influential national figures and other well-known celebrities. Every once in a while, however, the painted portrait of a complete stranger is completely captivating.

A collection of vintage portrait paintings up a staircase wall
This collection in a small cottage that interior designer Allison Kandler designed for her mother’s Santa Monica, California cottage is arranged to fit the staircase perfectly.

Enigmatic Personalities

There’s a sense of mystery to be savored in vintage portrait paintings of unknown people. When faced with the painting of a stranger, we see a piece of history represented before us–with old-fashioned hairstyles and outmoded clothing–in a way that emphasizes the differences between life then and the way things are now.

However, these distinctions don’t seem to matter when the empathetic expressions in carefully rendered faces draw us in and cause us to wonder what each sitter is thinking. We create stories that suit our perception of their personality and, in doing so, become familiar with someone we’ve never met.

Related reading: The One Fail-Safe Way to Collect

vintage portrait painting on pink shabby painted armoire filled with bathroom storage
Designer Alison Kandler’s bathroom boasts this fabulous chippy pink painted armoire. The sweet portrait displayed in the center punctuates the space with femininity and charm.

These stories told in the expressive faces of portrait paintings lend themselves to the overall narratives we create through our interior décor. The interpreted intelligence of a person with bright eyes and thick glasses fits right in with the studious ambiance of a reading nook. The flirtatious spirit seen in unruly curls and a knowing smile creates a completely different mood.

 Coordinate a theme that unifies a collection as a whole. Look for pieces with similar color palettes and brushwork, or create a grid-like gallery wall by using canvases that are all the same size.

pink guest room with wicker settee and a vintage portrait
This flea-market portrait of a woman in repose perfectly compliments the colors of Alison Kandler’s guest room and adds to the relaxing and peaceful vibe of the space.

Collecting Vintage Portrait Paintings

As with any work of art, consider how these pieces will work with the room as a whole when choosing where to hang them. Displaying one portrait alone increases that character’s importance in the surrounding space, perfect for showing off a painting that is large, highly detailed or depicts a unique personality.

If you plan to assemble a collection, coordinate a theme that unifies the group as a whole. Look for pieces with similar color palettes and brushwork, or create a grid-like gallery wall by using canvases that are all the same size. For a more whimsical take, limit the display to portraits of people with similar attributes, such as men with impressive facial hair or women and their pets. In the end, a home filled with portraits is filled with character.

Price Points

Where you purchase your vintage portrait paintings will have an impact on how much each piece will cost—garage sales on one end and art galleries on the other—but there are other factors in the work of art itself that influence its price.

  • Condition: Flaking paint, rips or punctures to the canvas and markings will all lower the value of any artwork. The visible signs of age can add to a painting’s charm, but if complete perfection is your goal, factor the cost of restoration into your budget.
  • Artistic Quality: As often as we think “my five-year-old could have done that” when we look at works in a museum, the mistakes made in amateurish art and absent from the work of more refined talent can be unsettling. Or, conversely,
    appealing! Expect to see portraits with greater detail carrying a higher price tag.
  • Media: Oil portraits are generally considered the most desirable, followed by acrylic and watercolor. Sketches in pastel, charcoal or graphite will be significantly less expensive.
  • Signatures: These little inscriptions are worth noting. A recognizable signature means the piece can be researched and, if the artist is recorded, a price point can be more accurately evaluated.

Got the collecting bug? Check out these posts on collecting transferware dishes or depression glass.

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