Gift Guide · Updated October 31, 2026

Gifts for the Man Who Has Everything

He already owns the watch, the car and the good bourbon. When a man can buy anything he wants, the best gift is the one he would never think to buy for himself.

These are the fifteen pieces I would put at the top of any list for him: things he will use every week, or remember for the rest of his life.

Diana Ostroff, Founder

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Longevity & Recovery · Diana's Collection

Eclipse 2-Person Red Light Infrared Sauna

Sun Home Saunas

Full-spectrum infrared heat with red light therapy built in, so one session does both. Sun Home's best seller, sized for two, with a limited lifetime warranty.

$9,999 Approx. price; check Sun Home for current holiday offers. Needs a dedicated 30-amp outlet; plan on an electrician Shop at Sun Home Saunas
Bar & Cigar · Diana's Collection

Intarsia Humidor Cigar Box

Loro Piana

Cedar and mahogany with calfskin trim and a cashmere-lined lid, plus a built-in humidifier and hygrometer. Quiet Italian luxury for his cigars.

$8,400 Approx. retail Shop at Loro Piana
Motorsport

Monaco Grand Prix 2027, St Devote Hospitality

P1 Travel

Saturday and Sunday at the most glamorous race of the year, from a lounge overlooking the first corner: champagne reception, open bar, gourmet menu and live entertainment. June 2027.

€6,150 Per person; other Monaco packages from €4,100 View the packages
Watches · Diana's Collection

Viceroy 8-Piece Watch Winder

WOLF

Keeps eight automatic watches wound, set and displayed in a lockable leather cabinet. For the collector whose watches outnumber his wrists.

$3,740 From; varies by retailer Shop at WOLF
Milestone Birthday

A Watch from the Year He Was Born

Chrono24

For the 50th or 60th: a vintage Rolex, Omega or Patek made in his birth year, from Chrono24's verified dealers. Ask the dealer for the watch's papers to confirm the year.

See price Depends on the brand and year you choose Shop at Chrono24
Riviera & Mediterranean · Diana's Collection

Portofino Automatic

IWC Schaffhausen

Named for the Italian Riviera harbor: a slim, elegant 40mm automatic with a discreet date, made for linen shirts and long lunches by the water.

$5,400 IWC boutique price (ref. IW356501); Chrono24 prices vary by dealer Shop at Chrono24
Bar & Cigar · Diana's Collection

Harmonie Decanter with Octogone Case

Baccarat

A square crystal whiskey decanter wrapped in a hand-finished leather case with octagonal windows that show the amber inside.

$1,700 Decanter $1,400 + case $300 Shop at Baccarat
Library · Diana's Collection

The Ultimate Tower (Black)

Assouline

A sculptural display tower for his Ultimate Collection books, turning a personal library into the focal point of the room.

$5,900 Approx. retail Shop at Assouline
Jewelry · Diana's Collection

Ropes Ring with Black Diamonds

Rockford Collection

Solid gold with 0.30ct black diamonds, handcrafted in the USA. Engraving available.

$3,540 Approx. retail Shop at Rockford Collection
Home & Study · Diana's Collection

Santos de Cartier Ballpoint Pen

Cartier

Brushed metal with palladium-finish screws borrowed from the Santos watch. The pen he'll reach for at every signing.

$930 Approx. retail Shop at Cartier
Golf

iO Home Simulator

Trackman

The tour's favorite launch monitor, mounted on the ceiling. Turns a spare room into a year-round practice bay.

$13,995 From; enclosure and mat extra Shop at PlayBetter
Longevity & Recovery

Plunge All-In

Plunge

A plug-in cold plunge with the chiller built inside, down to 37°F. Pairs naturally with a sauna.

$9,990 List price; often on sale Shop at Plunge
Retirement

Eames Lounge Chair and Ottoman

Herman Miller

The 1956 design, still made by Herman Miller with a five-year warranty. The chair he finally has time to sit in.

$9,695 Approx. retail Shop at Herman Miller
Sound & Vision

Q3 43 Camera

Leica

A full-frame compact with a fixed 43mm lens. Small enough for travel, serious enough for a photographer.

$6,895 Approx. retail Shop at Leica
Normatec 3 Legs by Hyperice
Longevity & Recovery

Normatec 3 Legs

Hyperice

The compression boots elite athletes use after training. Air pulses up each leg in waves to move circulation after golf, tennis or a long flight. Most models are FSA/HSA eligible.

$899 Standard size; Short and Tall also available Shop at Hyperice

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