Afew weeks ago, we introduced you to a selection of fine watches available at prices up to £3,000. Now, we shift gear from entry-level to mid-range, adding a not-insignificant £2,000 to the budget. So, what can you get for your money? Or, assuming that you’ve read the first feature in this series, what more can you get for your money?

In this journey to the centre of the fine watch market, we’ll revisit some of the brands that featured previously and see what additional bells and whistles an extra couple of thousand pounds can afford. We’ll also welcome into the stable a couple of highly esteemed watchmakers offering serious brand cachet at a price that’s still, in fine watch terms, very much at the affordable end of the spectrum.

There’s plenty more to see, of course. Precious metals remain tantalisingly out of reach, as do the Piagets and Jaeger-LeCoultres of this world. All that’s to be touched upon in our next edition, when we bump up the budget yet again to a lavish £10,000. For now, though, enjoy the best of what’s available for up to £5,000.

Value is something of an abstract concept in the fine watch world, not least because every brand has its own price point. Having said that, this particular variable can be nullified by comparing two different watches from the same watchmaker. Let’s give it a go, shall we? Exhibit A: Bremont’s dressy, elegant Airco Mach 2, which featured in our Best Watches Under £3,000 list, retailing at £2,895. Exhibit B: the same brand’s dressy, elegant ALT1-Classic/CR, which makes it into this list, retailing at £4,895. So, what do you get for your extra £1,500? The answer, in this case, is a chronograph. Stopwatch functionality is provided by the chronometer-rated BE-50AE movement, a modified version of the highly versatile Valjoux 7750, which can be found beating away inside Bremont’s 43mm-wide, 16mm-deep Trip-Tick case. This is a hefty number, in case those measurements didn’t make clear and, despite its understated looks, it’s not one we’d recommend slipping under the cuff of a dress shirt. More of a dressy sports watch than a sporty dress watch, we’d match it with relaxed tailoring and a woven leather bracelet or two.

Watchmaking’s long history with motorsports has thrown up countless special-edition watches that claim to embody the spirit of automotive engineering. Few of them can claim to have been designed by a carmaking legend. Baume & Mercier’s range of Shelby Cobra chronographs was created in collaboration with Mr Peter Brock, the automotive engineer responsible for the Shelby Cobra Daytona Coupe, a radical experiment in aerodynamics that set a new GT-class speed record of 196mph at Le Mans in 1964. Look for subtle details that reference Shelby’s iconic racing car, such as the pedal-shaped pusher buttons at two and four o’clock, the dashboard-inspired subdials and the oscillating weight – visible through the sapphire-crystal case back – that’s designed to resemble the shape of the wheels. An attractively priced chronograph from one of Switzerland’s longest-established horological houses, this is a great choice for petrolheads and watch lovers alike. If you’re willing to stretch the budget a little further, look out for the brand’s flyback chronograph with bi-colour dial, which was released in a limited run of just 196 pieces.

A budget of £5,000 gives you access to a number of IWC Schaffhausen’s more affordable timepieces, from the functional diving watches of the Aquatimer family to the tasteful dress watches of the Portofino family. They’re all worth a look, but we’ve chosen to focus on the Pilot’s range, and specifically the chronographs, as it’s here that you’ll find the purest expression of IWC’s signature brand of functional, no-nonsense watchmaking. (This is a company whose initials stand for nothing more complex than International Watch Company, after all.) The watches come with black dials as standard, but brown and blue are also available as part of the brand’s long-standing collaboration with the Antoine de Saint-Exupéry Youth Foundation. The brown dials are named after the French aviator himself, while the blue dials are named after his celebrated children’s book, Le Petit Prince. It’s the former we’ve selected here – we just can’t get enough of that tobacco-brown dial alongside the calfskin leather strap – but it’s really a question of personal preference. Any of these chronographs would be a worthy addition to your collection, not to mention a great introduction to the IWC brand.

TAG Heuer’s Monaco chronograph is perhaps the greatest example of a “celebrity watch”, by which we mean a watch that was originally made famous by a celebrity. There are others, of course, but most are exotic rarities. Rolex’s sought-after “Paul Newman” Daytona springs to mind. In terms of what’s currently available, though, it’s fair to say that no watch is so closely associated with one man as TAG Heuer’s square-cased, blue-dialled beauty is with Mr Steve McQueen. The King of Cool wore it on-screen in 1971’s Le Mans after picking it out from a selection sent to him by Mr Jack Heuer, the great-grandson of the brand’s founder, and the rest is horological history. A near-perfect visual match for the 1969 original, the Monaco Calibre Heuer 11 is a steal at under £5,000, especially when you consider that the first remake – a 40-year anniversary edition released in 2009 – retails for roughly double that price.

The eye-catching Desert Type range from Bell & Ross takes the sandy colour of the flight suits worn by fighter pilots on desert missions and applies it to the dial and leather strap. It’s a bold choice, and tentative first-time buyers might prefer to start their collections with something a little more conservative, such as a black-dialled BR 03-92 or the smaller BR S. Then again, perhaps conservative isn’t what you’re going for. It certainly isn’t what Bell & Ross is known for. With chronograph functionality coming courtesy of its automatic calibre BR-CAL.301 movement, the BR 03-94 is a highly functional pilot’s instrument and, at 42mm, it’s a serious presence on the wrist, too. The colour is surprisingly easy to wear, though, especially against tanned or darker skin, and looks great emerging from the ribbed cuff of a bomber jacket.