At this price range you will more than likely see what my biases are. You can get even more intricate watches as well as watches with cases made of precious metals. You can also get a lot of iconic watches in this price range. All prices are in USD.
Breitling Navitimer B01 Chronograph 46 ($8,680)
I would argue this is the most iconic pilot watch that is available on the market. The dial of this watch is incredibly busy, but it is executed so perfectly that it just makes sense and does not feel difficult to read at all. It comes with an automatic movement with a power reserve of 70 hours. The case back of the watch allows you admire the movement and both the case back crystal and the front are made of sapphire. You can also get the blue dial version for the exact same price from Breitling themselves.
Jaeger-LeCoultre Master Ultra Thin Moon 1368420 ($9,850)
This is my favourite dress watch. I love the elegance this watch shows as well as that striking blue second hand in contrast to that silver dial. As well as the main feature of the moon phase sub dial. The case is made of stainless steel and with a diameter of 39mm. The thickness staying true to its name is 9.9mm thick which is even more impressive considering the automatic movement inside the watch that has a power reserve of 38 hours. The case back of the watch also features an exhibition window that shows off that incredible movement.
Panerai Luminor Blu Mare PAM01085 ($5,500)
This watch design and style is very iconic to Panerai and for good reason. Despite the unique look it is an incredible watch. This particular model is a hand wound mechanical with a power reserve of 3 days. It has a case diameter of 44mm which is quite big for a watch, I would recommend wearing it first before you purchase the watch to see if it fits your wrist. It comes with a 100m water resistance and comes with sapphire crystal as well. This particular model comes with calfskin leather in dark blue with some beige stitching which compliments the watch beautifully.
Rolex Lady-Datejust 179163 ($8,000)
This particular model you will have to buy pre-owned but for the price you get a very iconic watch with a 26mm case diameter. This watch comes with an 18 carat yellow gold case and can come in either the oyster bracelet or the jubilee bracelet. It has an automatic movement with sapphire crystal, and a beautiful black dial with gold hour markers and hands. There is also the iconic cyclops over the date indicator that you would find on a Rolex.
Hublot Classic Fusion Titanium Diamonds 33mm ($8,500)
A great watch from a very distinguished and well-known brand. This watch combines the classic look of the classic fusion by Hublot and changes the bezel to be covered with diamonds (0.8 carat). The case is made of titanium and has a water resistance of 50m. The crystal as usual with watches at this price range it comes with sapphire crystal with an anti-reflective treatment. This does come in with a quartz movement. If diamonds are not your style, you can get the normal classic fusion for $5,200. I much prefer the normal version than the diamonds, but if you want to have diamonds you can for $8,500. They also have case sizes ranging from 33mm, 38mm, 42mm and 45mm. The case size of 33mm will have the quartz movement while any other size will have an automatic movement.
If you want to see watches cheaper than this click here to see watches between $2,000 and $5,000. If you want to see watches more expensive than this click here to see watches priced higher than $10,000.