Commission an Oil Portrait
by Jonathan Sherman
Timeless oil portraits capturing the essence of each subject — serving Boston and greater New England.
Collected by private patrons including the van Otterloos, whose collection now resides at the Museum of Fine Arts, Boston
Beyond Likeness
Image suggestion: In-studio photo, palette, or easel.
“The painter who draws a head well is a master of all.” — Leonardo da Vinci
Each portrait begins with a conversation — an exploration of vision, presence, and meaning. In a world saturated with digital images, a painted portrait offers authenticity and permanence. Sherman’s oil portraits are created on hand-prepared supports using classical techniques, producing works of enduring beauty and depth.
Whether for a family, a professional institution, a corporate setting, or a beloved pet, each portrait is conceived as a legacy — created to be appreciated for generations. First-time commissioners are guided step by step, ensuring your vision is realized and your portrait reflects both your individuality and the life you wish to celebrate.
The Artist’s Lineage &
the Sight-Size Tradition
In the atelier tradition, technique is not mechanical—it is a philosophy of seeing. Jonathan Sherman’s work is rooted in the sight-size method, whereby the sitter and canvas are placed side by side at a fixed distance, allowing the eye to perceive the whole objectively. Rather than focusing on detail alone, the artist steps back, sees the work in full scale, and lets form, light, and gesture emerge in unity.
This approach is not new: sight-size was used by masters such as Van Dyck, Reynolds, Sargent, and Titian, and was preserved in the Boston atelier lineage of R. H. Ives Gammell and his protégés.
Sherman’s influences reach deep — from Leonardo and Michelangelo’s devotion to form and proportion, to Rembrandt’s psychological intimacy, to Sargent’s bold facture and expressiveness. These impulses inform his thinking, but never overshadow observation.
Portraiture is at once intimate and sculptural: the head is exquisite because it embodies all of gesture, proportion, flesh, and spirit. In painting the likeness, one engages not just resemblance, but presence. The sight-size method disciplines the eye so that every brushstroke contributes to coherence and truth, and allows the artist to omit what is unnecessary and reveal what is essential.
About the Artist
Image suggestion: Jonathan working from life with a sitter.
Jonathan Sherman trained at the Charles H. Cecil Studios in Florence, a direct continuation of the atelier tradition of R. H. Ives Gammell and the Boston School. (1) He employs the sight-size method, observing sitter and painting at true scale to achieve exceptional accuracy, proportion, and subtle alignment of form. or (2) This lineage situates his work within a distinguished heritage of classical oil painting.
Jonathan draws inspiration from the great portraitists of history — Leonardo da Vinci, Michelangelo, Rembrandt, Van Dyck, and John Singer Sargent — balancing classical technique with contemporary perception.
His paintings, drawings, and sculptures are housed in private and corporate collections across the United States, Europe, and Australia. Eleven works reside in the private collection of Eijk and Rose-Marie van Otterloo, whose world-renowned Dutch and Flemish collection — including works by Rembrandt, Vermeer, and Frans Hals — is now part of the permanent collection at the Museum of Fine Arts, Boston.
He has completed over forty commissions, including a recent bronze sculpture series for Maddox & Partners in Naples, Florida, and his works have been exhibited at The Crane Estate (Ipswich, MA), The Edwards Art Gallery (Plymouth, NH), and Lo Studio dei Pittori (Florence, Italy).
The Commission Process
Commissioning a portrait is a deeply personal experience — a collaboration between artist and sitter that unfolds through conversation, observation, and craftsmanship. Each portrait begins with dialogue and ends with a work that endures for generations.
1. Initial Conversation: Defining the Vision
Every commission begins with an open discussion — ideally in the studio, though phone or video consultations are also welcome.
This is a chance to share your inspiration and intentions: is the portrait a gift, a family heirloom, or a commemoration? We’ll look at examples, discuss style and scale, and talk about the emotional character you wish the painting to hold.
Clients often bring photographs, personal stories, or meaningful objects that express the spirit of the sitter.
(Optional visual: image of studio / sample sketches)
2. Composition, Medium & Setting
Once the vision is clear, we determine composition and technique — from a classic head-and-shoulders study to a full-length composition including symbolic objects or architectural settings.
Jonathan works exclusively in oil on hand-prepared linen or panel, ensuring depth, permanence, and beauty of surface.
For those wishing to include companions, children, or pets, the artist will sketch compositional studies to balance naturalism and narrative harmony.
(Optional visual: drawing / compositional study)
3. Sittings & The Experience of Working from Life
Whenever possible, Jonathan prefers to paint from life. Sittings are arranged in the Marblehead studio or, for larger projects, on location.
The number and length of sittings vary depending on scale, but each session offers a calm, reflective rhythm — a time to sit, observe, and participate in a process that artists have followed for centuries.
For clients unable to travel, portraits may be executed from carefully selected photographs, though painting from life remains the truest path to depth and presence.
(Optional pull quote or sidebar: “A photograph may record appearance; painting from life reveals being.”)
4. Progress & Approval
Throughout the process, you’ll be kept informed with updates and opportunities to view the portrait as it develops.
Adjustments to likeness, tone, or mood are made thoughtfully and collaboratively. Once the painting reaches completion, it will rest in the studio to dry before varnishing and presentation.
5. Presentation & Delivery
Upon completion, the finished work may be viewed in the studio, beautifully lit and displayed.
After approval, the portrait is prepared for framing or delivery. For distant clients, professional shipping can be arranged with custom crating.
Each painting is accompanied by documentation of materials, process, and care recommendations to ensure its longevity.
6. Investment, Deposit & Contract
Prices vary according to scale, number of figures, and complexity of composition. A signed contract secures your commission, outlining all logistics and protecting both client and artist.
A 50% deposit begins the work, with the balance due upon completion and approval.
For commissions more than two hours’ travel from the Marblehead studio, additional costs for travel and lodging apply.
When in-person sittings are impractical, Jonathan may work from carefully selected photographs, though painting from life remains the preferred and most rewarding approach.
7. Framing & Legacy
The Studio offers framing consultation and coordination for an additional fee of $500. Many clients choose handcrafted frames that complement the painting’s style and setting.
We are proud to work with Guido Frames, an atelier specializing in hand-carved and hand-gilded frames made using traditional techniques. Each frame is designed to harmonize with the painting’s tone, composition, and period sensibility — ensuring that the portrait’s visual integrity is complete.
Once framed, the work becomes part of a lasting legacy — whether cherished as a family heirloom, presented as a gift to an institution, or commissioned to honor leadership and service.
Investment Overview
Portrait commissions are unique in scale and composition. Below is a guide for typical projects:
Type of Portrait
Approximate Size
Investment
Head & shoulders (Youth)
16 × 20 in.
$15,000
Head, shoulders & torso
20 × 24 in.
$17,500
Head, shoulders, hands & object
20+ × 24+ in.
$20,000
Half-length with objects
36 × 42 in.
$25,000
Half-length with full background (e.g., library, garden)
36 × 42 in.
$35,000
Please note: Travel beyond a two-hour radius of Marblehead, Massachusetts — including the Berkshires or out-of-state sittings — requires additional arrangements for travel and lodging.
Types of Commissions
Every portrait begins with a conversation — about the person, the place, and the purpose behind it. Jonathan paints portraits for families, institutions, and individuals, each with its own kind of meaning.
Family Portraits
A celebration of presence and kinship. These works often mark milestones — a child’s coming of age, a wedding, or a family gathered at home — preserving the grace of ordinary moments made extraordinary through paint.
Individual Portraits
Whether for personal reflection or professional legacy, an individual portrait honors the depth of a single life. Painted from life in the studio or on location, each likeness becomes a meditation on character and time.
Children’s Portraits
Painted with sensitivity and care, children’s portraits capture the fleeting years of innocence and growth — the wonder that changes almost daily, yet remains timeless on canvas.
Institutional & Corporate Portraits
From universities and hospitals to boardrooms and civic spaces, these portraits recognize service, leadership, and distinction. Jonathan’s approach balances dignity with vitality, ensuring each sitter is portrayed with warmth and integrity.
Pet Portraits
Our companions deserve no less care. Pet portraits are painted with the same devotion to character and naturalism — honoring the quiet joy, humor, and loyalty that animals bring to our lives.
Why Commission an Oil Portrait?
Image suggestion: Life painting close-up, brush and palette.
In an age of fleeting digital images, the painted portrait endures as one of the most profound expressions of human connection. To commission a portrait is to honor not only a likeness, but a life — to affirm that a person, in this moment, is worth truly seeing.
Within the long tradition of New England portraiture — from John Singleton Copley to Sargent and the Boston School — this art form has been cherished for its ability to unite intimacy with permanence. Jonathan Sherman continues that lineage, working from life in the classical sight-size method to reveal presence, temperament, and inner light with honesty and grace.
An oil portrait painted from life gathers time rather than freezing it. Through hours of observation, the artist comes to understand not just a sitter’s features, but their essential spirit. Light, color, and form become the language through which affection, intellect, and vitality are recorded — not merely as representation, but as remembrance.
Such works become part of a family’s story — a gesture of continuity and care. They speak to heritage, to gratitude, to the wish that beauty and meaning endure. Whether for a family home in Concord, a university in Cambridge, or a company honoring its founders, the painted portrait remains what it has always been: a lasting symbol of esteem, and of the human desire to be known.
“To paint the living likeness is to capture truth itself.” — Georgio Vasari
Why Commission from Life?
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Painting from life allows the artist to discern what is essential, leaving aside irrelevant or distracting details. Only in this environment can naturalism and imagination fully converge, producing a portrait that captures character, gesture, and presence. A photograph preserves likeness, but it cannot convey the interplay of light, form, and human spirit that emerges in the studio.
working form life vs. photograph
Image suggestion: Life painting close-up or hands at palette.
Whenever possible, Sherman prefers to work from life, capturing subtle light, gesture, and presence that photographs cannot convey.
For distant clients, work from photographs is possible; the artist encourages life sittings whenever feasible for the most meaningful and artistically significant results.
Client Reflections
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“Jonathan’s portrait captured the essence of our family in a way that feels timeless and alive.” — [Client Name, Boston]
“A deeply moving collaboration — the finished work exceeded every expectation.” — [Client Name, Newton]
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Artist Statement
“My work is rooted in a deep love for human beings and the human experience. Depth of beauty, harmony, spiritual richness, and radiant energy permeate each piece. By using the language of nature — light, shadow, form, proportion, color, and texture — I am able to fix timeless truths on canvas, paper, or in bronze, reflecting the ever-present relationship between human and spirit. My works of Art are to soothe the body, nourish the intellect, and uplift the spirit. Preparing my materials by hand ensures sound craftsmanship, enabling them to endure for centuries or millennia for future generations to benefit from.”
— Jonathan Sherman
Begin the Conversation
A commissioned portrait is a collaboration — an exchange that results in a lasting work of art. Jonathan Sherman accepts a limited number of commissions each year to ensure the highest level of attention and craft. Early inquiry is encouraged.
The Studio of Jonathan Sherman
112 Washington Street
Marblehead, Massachusetts 01945
Serving Boston, Newton, Concord, Cambridge, Brookline, Wellesley, and greater New England.