A watch is so much more than a device to tell time. A watch accompanies you through life’s important moments. It’s there with you on good days and bad, and it often outlasts you, finding a home in the collection of the next generation of watch lovers. Worn proudly on the wrist, a great watch can hold memories and represent dreams and hopes, character and style like few other objects.
Selecting that perfect watch as a gift can be a bit daunting, however. There’s a lot to think about if you’re diving into the world of luxury watches. This watch gift guide takes the stress out of your search. Watches have been organized into several price points and styles. Each watch in this collection can be found on the Bob’s Watches website. They all are 100% certified authentic and will ship fully ready to surprise and delight.
Under $5,000: Accessible Luxury
Models on this list show that ultra-luxury doesn’t start at $100,000+. In fact, some of these brands have what we believe are strong entry points offering you true craftsmanship, history, and that special feeling on your wrist. These watches are the first ones you’ll likely buy that are serious horology, without the heartbreak of six-figure price tags.
Sporty and with an in-house movement, the Tudor Black Bay collection has it all. For dress watches, check out the Tudor 1926, which starts at just $2,150. If you are ready to buy your first Rolex, try the manual-wind Oyster Precision (Ref. 6426) and OysterDate (Ref. 6694) models which are both under $5,000. Both models have that famous crown logo and have vintage inspired vibes. The Breitling Avenger Chronograph is an adventurous, aviation-inspired timepiece for about $2,995. Vintage Omega cocktail watches can be a good entry point too, and are one-of-a-kind in this price range. They can retail for as low as $1,200 and around $3,000. These watches come with the jewelry-like vibes but with a mechanical heart.
Under $10,000: The Sweet Spot
With this range, you can enter the realm of truly iconic watches, instantly recognizable and universally revered. This level affords an extra touch of finer materials, more prestigious references and watches with a larger presence on the wrist, while maintaining a level of relative accessibility, and true substance.
Rolex sets the standard with the Datejust 36. The classic two-tone Ref. 16233 or unique Thunderbird Ref. 16264 is a fit for almost any situation, be it casual Friday or business formal. Rolex Air-King Ref. 14010 is a more understated, unisex design and at around $5,495 pre-owned, is among the most affordable in this series. Engine-turned bezel adds just the right amount of unique flavor. For an entry into the “go anywhere, do anything” club, you can’t do better than the Omega Seamaster Aqua Terra, with refined finishing and water resistance. Splitting the difference between past and present is the Breitling Superocean Heritage, a watch for any fan of retro design.
Men’s Classics: The Heavy Hitters
Some watches are a no-brainer. Icons that set the standard for their segment, references spoken about by horology fanatics for ages, the ones that hold value through recessions and depressions. When you’re looking for a no-fail gift that clearly makes a statement, these are the big guns.
Rolex Submariner
The Submariner is king of dive watches for a reason. Reference 126610, the latest iteration, or its predecessor, Ref. 116610, are models that work just as well on the weekend as they do dressed up for the office. The rotating bezel, luminous markers, 300 meters of water resistance, are all features for serious scuba, but the clean aesthetic translates just as nicely with a suit. It’s no surprise then that the Submariner is one of the most popular watches in the world.
Rolex GMT-Master II
GMT-Master II is the watch for frequent travelers and aviation fans, thanks to the dual time-zone feature. The “Batman” (Ref. 126710BLNR) and “Batgirl” versions come with a boldly striking blue and black bezel, now an instantly recognizable aesthetic. The attractive design isn’t just for show, as the independent hour hand adjustment is genuinely useful for frequent time zone travellers. This is the watch to have when you have ambitions to travel further than your hometown.
Omega Speedmaster Professional
NASA qualified the Speedmaster for space in 1965 and first traveled to the moon in 1969. It’s a history few timepieces can match. The manually-wound chronograph movement, hesalite crystal, and design that hasn’t changed are all the product of engineers, history buffs, and those who simply love objects built for demanding specifications. This is a watch for someone who appreciates substance and heritage.
Women’s Classics: Elegance Meets Engineering
The best women’s watches combine great looks with serious watchmaking. They are not jewelry pieces that tell time. They are proper watches that are also sophisticated accessories, many with complications and finishing to match any men’s watch.
Rolex has set the bar very high with the Lady-Datejust 28 Ref. 279174 in White Rolesor. The 28mm case size is ideal for a more petite wrist and the dials are large enough to be both full-figured and highly legible. Rolex also offers a slightly larger Datejust 31 (Ref. 278243 in steel and gold here) as a more contemporary and slightly larger option that works well on most women, even with a few preferences for more full-bodied watch styling.
From Cartier, the Tank Must and Tank Française designs are some of the most iconic luxury watches of all time with their instantly recognizable rectangular case and Roman numeral dials. The Rolex Yacht-Master 37 provides a sporty timepiece option with identical mechanics to the Yacht-Master 40 in a size that works well for women seeking a contemporary bold look. Every watch here reflects a real understanding of the woman who wears it. Smart, discerning, and effortlessly stylish.
Luxury Icons: The Ultimate Statement
Some watches transcend typical luxury, representing the pinnacle of their makers’ craft and serving as ultimate achievement markers passed down as family treasures. When budget allows for something truly special, these icons deliver.
Nicknamed “The President’s Watch,” the broader Rolex Day-Date was favored by leaders and captains of industry for generations. Rolex Day-Date 40 models like the platinum Ref. 228206 with ice blue dial or Everose gold (Ref. 228235) speak success silently and only in platinum and gold. Rolex Sky-Dweller (Ref. 326935 in Everose gold) impresses with a smart Ring Command bezel system and a technical tour de force with its annual calendar complication.
The Audemars Piguet Royal Oak (Ref. 15500 or similar) revolutionized luxury sports watches when Gerald Genta designed it in 1972. Its integrated bracelet, exposed screws, and “Grande Tapisserie” dial pattern remain influential decades later. The Rolex Daytona, particularly the Ref. 116500 with white “Panda” dial or precious metal variations, continues its reign as the chronograph everyone wants. These pieces represent not just purchases but investments in mechanical artistry and cultural significance.
Vintage Edit: Gifts with a Story
Vintage watches have one thing new watches can never hope to have: history. The dial patina, bezel wear, and differences between production runs are stories that brand-new watches require decades to gather. If you want that genuine vintage feeling, the Rolex GMT-Master Ref. 1675 is a great start. With its “Pepsi” bezel and matte dial (gloss dial on earlier versions), each one produced between the 1960s and 1980s has an authenticity born from a lifetime of travel and use.
The Rolex Submariner Ref. 5513 is a purist’s dream with its simple two-line dial and acrylic crystal that only gains a unique patina of warmth over the years that new sapphire can never match. Vintage Datejust watches like the Ref. 1601 and 1603 showcase Rolex’s discontinued “pie-pan” dial with its signature sloping design.
A special way to make a vintage watch really mean something to the recipient: track down a watch from their birth year. That gives your gift both personal significance and mechanical history. With Bob’s Watches’ massive inventory, that’s a search you can actually pull off for several decades.
