

Victorian Winking Man-in-the-Moon Ruby and Diamond Gold Cufflinks
Whimsical Victorian Gold Cufflinks Featuring Winking, Smoking Faces Set with Rubies and Diamonds
An extraordinary pair of Victorian gold cufflinks featuring whimsical winking and smoking faces, beautifully detailed with rubies and diamonds. Full of humor, personality, and artistic imagination, these unusual cufflinks capture the playful spirit and remarkable craftsmanship of Victorian jewelry.
Each rounded gold face displays a mischievous expression, with one eye playfully closed in a wink and the other set with a sparkling diamond. A vibrant red ruby adds a delightful touch of color to the smoking motif, enhancing the character and individuality of each face.
The cufflinks feature a traditional double-sided construction, with four individually modeled faces connected in pairs by gold bars. Their expressive features, rounded cheeks, exaggerated smiles, and carefully worked gold surfaces create a wonderful sense of depth and personality.
The combination of rich yellow gold, precious gemstones, and imaginative Victorian design makes these cufflinks especially appealing. Both elegant and humorous, they reflect an era when fine jewelry often incorporated unusual subjects, symbolism, and artistic expression.
A distinctive example of Victorian gentlemen's jewelry, these cufflinks offer a rare opportunity to own a conversation piece that combines fine craftsmanship with unmistakable charm.
Key Features
- Period: Victorian
- Metal: Yellow gold
- Design: Winking and smoking faces
- Gemstones: Rubies and diamonds
- Diamond Details: Diamonds set in the open eyes
- Ruby Details: Rubies positioned near the mouths
- Motif: Whimsical, expressive human faces
- Construction: Double-sided cufflinks with connecting gold bars
- Goldwork: Detailed facial modeling with polished and textured finishes
Collector's Note
Victorian novelty jewelry is particularly admired for its imaginative subjects, intricate craftsmanship, and distinctive sense of humor. These remarkable cufflinks embody that tradition, featuring four mischievous smoking and winking faces brought to life through beautifully modeled goldwork, sparkling diamonds, and richly colored rubies. Their unusual design and expressive character make them a fascinating addition to a collection of Victorian jewelry or antique gentlemen's accessories.
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The DSF Promise
Buy with confidence. Every piece is backed by:
• Authenticity — examined and verified before listing
• Condition — carefully inspected and honestly described
• Insured shipping — fully insured, signature required
• 32-day returns — available on eligible, unaltered items
• Private appointments — available in New York
• Experience — over 50 years of fine jewelry expertise
How do I know a piece is authentic, and can I trust DSF?
Buying fine jewelry online takes trust, especially at this level. DSF Antique Jewelry is a New York–based dealer with over 50 years of fine jewelry expertise. Every piece is examined for authenticity and condition before it is listed — we assess hallmarks, maker's marks, metal content, gemstones, and construction consistent with the stated period or designer. For signed pieces such as Cartier, Buccellati, or Van Cleef & Arpels, we verify maker's marks and signatures. We're glad to send additional photographs of any hallmark, or speak with you directly, before you decide.
Why does antique gold look different, and is surface wear normal?
Antique pieces were often made in gold standards less common today, such as 15ct (used in Britain only between 1854 and 1932), 9ct, or higher-karat continental gold, which give a warmer tone than typical modern 14k. Light surface wear, softened edges, and a gentle patina are normal and expected on antique jewelry — they reflect the age and authenticity of the piece, not flaws. We describe the true condition of every item honestly in its listing.
What do the hallmarks and maker's marks mean?
Hallmarks are small stamped marks that identify the metal standard, and often the maker, assay office, and date. They are one of the best tools for authenticating antique jewelry. We identify and explain the marks we find on each piece in its description, and we're happy to send close-up photographs of any hallmark on request so you can see exactly what you're buying.
Can pieces be resized or adjusted?
It depends on the piece. Many antique rings can be resized, but bands with all-around engraving, thin shanks, or gemstones near the base may be limited in how far they can safely go, and some pieces are best left as-is to preserve their integrity. We list each item's measurements as they currently are. If you're unsure whether something can be safely adjusted, contact us before buying and we'll give you an honest assessment for that specific piece.
How should I care for and store fine jewelry?
Clean gently with a soft cloth, avoid harsh chemicals, ultrasonic cleaners, and chlorine, and store pieces separately so they don't scratch one another. Remove rings and bracelets for heavy manual tasks. Antique gold is softer than modern alloys, so period pieces are best enjoyed with normal care. Treated well, fine antique jewelry lasts for generations — many of our pieces are already a century or more old and still beautiful.
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