Anniversary gifts for a boss who loves clothes
Ray-Ban
Aviator Classic Sunglasses (paid link)
$100 to $250 at Amazon
The aviator shape that made Ray-Ban a name everyone already recognizes, in a classic pair of sunglasses.
Seen at Amazon, 3 Sep 2026
Timex
Deepwater Reef 200 41mm Rubber Strap Watch
$239 at Timex
A dive style watch rated to 200 metres, on a rubber strap that survives the pool and the sea.
Seen at Timex, 18 Sep 2026
Tumi
Voyageur Holland Backpack, Leather (paid link)
Over $250 at Amazon
Tumi's women's leather travel backpack, a third signature shape from the brand.
Seen at Amazon, 3 Sep 2026
Shinola
Octagonal Onyx Inlay Cufflinks
$425 at Shinola
Octagonal cufflinks with an onyx inlay, for the next formal occasion.
Seen at Shinola, 8 Sep 2026
Assouline
From Louis to Vuitton
$250 at Assouline
Louis Vuitton’s history and design, presented in a Damier-style collector’s case.
Seen at Assouline, 8 Sep 2026
Rimowa
Original Cabin, Silver
$1,550 at Rimowa
The grooved aluminium carry-on that announces good taste before the suitcase is even opened.
Seen at Rimowa, 8 Sep 2026
S.T. Dupont
ICONIC Backpack, Navy
$1,295 at S.T. Dupont
An ICONIC canvas backpack with leather trim and the house’s signature tricolour detail.
Seen at S.T. Dupont, 8 Sep 2026
Breitling
Navitimer B01 Chronograph 43, Red Gold
$47,900 at Breitling
An 18k red-gold case and bracelet turn Breitling's pilot chronograph into an unmistakable statement.
Seen at Breitling, 8 Sep 2026
SteamLine Luggage
The Diplomat - Hunter Green Stowaway Spinner
$1,150 at SteamLine Luggage
A leather-trimmed heritage-green checked suitcase with four spinner wheels.
Seen at SteamLine Luggage, 8 Sep 2026
Assouline
Gucci: The Art of Silk
$250 at Assouline
Gucci’s silk-scarf archive becomes a richly illustrated book in a Flora-print slipcase.
Seen at Assouline, 8 Sep 2026
S.T. Dupont
ICONIC Travel Bag, Beige
$1,395 at S.T. Dupont
Canvas, leather trim and gold-tone details in an ICONIC weekend travel bag.
Seen at S.T. Dupont, 8 Sep 2026
Shinola
Coin Edge Money Clip
$595 at Shinola
A coin-edge money clip that makes an everyday accessory feel considered.
Seen at Shinola, 8 Sep 2026
Citizen
Eco-Drive Classic Day-Date Watch (paid link)
$100 to $250 at Amazon
A watch that runs on light and never needs a battery, from the brand that invented that technology.
Seen at Amazon, 3 Sep 2026
SteamLine Luggage
The Illustrator - Blue Carryon Spinner
$1,150 at SteamLine Luggage
A vintage-inspired carry-on with four spinner wheels and a distinctive blue finish.
Seen at SteamLine Luggage, 8 Sep 2026
S.T. Dupont
Crocodile-Embossed Leather Briefcase, Havana
$3,695 at S.T. Dupont
A crocodile-embossed calfskin briefcase with two main compartments and a hand-patinated finish.
Seen at S.T. Dupont, 8 Sep 2026
Tissot
PRX Powermatic 80, Blue Gradient Dial
$850 at Tissot
A Swiss automatic watch built on a design first sold in 1978.
Seen at Tissot, 3 Sep 2026
Shinola
Canfield Backpack - Emerald
$650 at Shinola
A pebbled-leather backpack with a laptop sleeve and luggage-handle slide.
Seen at Shinola, 8 Sep 2026
SteamLine Luggage
The Pioneer - Carryon Spinner
$1,150 at SteamLine Luggage
A full-grain-leather carry-on with spinner wheels and TSA-approved locks.
Seen at SteamLine Luggage, 8 Sep 2026
Shinola
Canfield Briefcase - Black Pebbled Leather
$595 at Shinola
A leather briefcase with a dedicated laptop pocket and a sleeve for a suitcase handle.
Seen at Shinola, 8 Sep 2026
Shinola
Canfield C56 Chronograph Watch - Cool Gray
$1,450 at Shinola
A cool-grey C56 chronograph with orange accents and an engravable caseback.
Seen at Shinola, 8 Sep 2026
Shinola
Canfield Duffle Bag - Espresso
$850 at Shinola
A structured pebbled-leather duffle with organised pockets for a weekend away.
Seen at Shinola, 8 Sep 2026
Shinola
Canfield Sport Watch
$790 at Shinola
A Canfield sports watch with chronograph subdials, a ceramic top ring and a leather strap.
Seen at Shinola, 8 Sep 2026
Shinola
Circadian Monster Automatic Watch - Daylight Blue
$1,695 at Shinola
An automatic Circadian Monster watch in Daylight Blue.
Seen at Shinola, 8 Sep 2026
Shinola
Runwell Zip Brief - Medium Brown
$995 at Shinola
Navigator leather, a padded laptop sleeve and room for overnight essentials in a substantial briefcase.
Seen at Shinola, 8 Sep 2026