I am a really big fan of classic chunky Rolex. Either the Submariner or GMT Master. Both of these watches represent classic style and historical importance. They look equally good with shorts and a t-shirt or a tux. If you want to have one watch that you can wear with anything and still look like a connoisseur, this is the watch for you!
I use a stainless steel, black face diver watch for my everyday "beater" - goes with jeans, a suit, and anything in between. Any diver watch that has that Rolex Submariner look should suffice as a classic, every-situation watch.
I wear my dress watch really only with a tux or at black-tie events.
My sportier watches (example: Omega Dynamic pilot watch or an orange bezel Planet Ocean) I will wear with shorts or in more casual situations only.
Ive got several watches for different occasions. I was fortunate to inherit a couple really nice vintage watches I save for special events. One barrel shaped gold Bulova and a round Hamilton. Being a constant traveler and a pilot my go to watch is the Citizen Skyhawk. Not only do I have the flight calculator slide ruler bezel... but Its global atomic. It syncs time to all the worlds atomic antennas. And I got it for about 50% off the msrp. I didnt know you could haggle on watches until I walked in... stated it was nice, but pricey. The salesman asked what I did for a living. When he heard I was in aviation I think the guy pictured me talking to all my pilot buddies and he gave me a fantastic deal.
If I didnt have the Bulova or Hamilton the Skyhawk turns heads all the time. Its very versatile.
Ive only got two.
Standard sports watch. Reliable as hell. Its a timex. Doesnt look pretty. Does the job though. I wear it when Im wearing t-shirts, etc.
Then I have a Kenneth Cole. Leather band watch. Got a chrome body with brown face, gold bezel around the face/glass. Beautiful. This thing gets compliments wherever I go. IMO, stainless steel bands are played out. Everyone has one, they all look the same unless you really really look hard. I wear it with Polo's and full button up's.
Go with something different, something that most people dont rock. Might not be a conversation starter in a bar, but at the coffee shop, different story.
If you are going to invest in a quality watch, be sure that it has a sapphire crystal. My everyday stainless watch (a Sector) is 11 years old and the crystal is perfect. This watch is appropriate for any occasion.
I also have a sportier Tag with a leather strap, again with a sapphire crystal. Good for daytime, business, weekends. I don't wear it in formal settings - it is too casual.
Consider vintage watches, too. I have a 14K antique Longines tank watch with a leather strap that always gets a compliment. It is formal - I rarely wear it during the day - the exception being if I am wearing a suit; then it is appropriate (IMHO).
Oh, and I'm looking forward to the day when I am given the family pocket watches. I intend to display them, though.
I agree with the choice of having a crystal face for an everyday watch. I have a titanium watch with a crystal face and it can take a beating. Titanium does not easily scratch, but it can be polished so, don't worry about scratches.
I don't like leather band watches. The trend of smaller watches for men vanished in the 90's. Most watch makers are going for a larger bezel with a metal bracelet. Every time I try to wear one of my older watches, I now think they look too small.
You buy the watch you want to wear and call it a day. Don't worry about what is considered right or wrong. Just like it!
There is no steadfast rule. Metal, rubber, or leather it's all about what you feel like sporting out and about. I have quite a "few" watches and I mix and match them for all sorts of occasions. A steel and rubber Bvlgari will look sporty with shorts and a t-shirt, rugged with jeans and a polo, and dressy with a suit and tie. Get something you love, decently sized (do not follow the extreme size [48mm and above] trends as they will disappear) from a quality manufacturer (there are many out there) and you will be happy.
I am a really big fan of classic chunky Rolex. Either the Submariner or GMT Master. Both of these watches represent classic style and historical importance. They look equally good with shorts and a t-shirt or a tux. If you want to have one watch that you can wear with anything and still look like a connoisseur, this is the watch for you!
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A go-to watch is your best choice for everyday use. It should be durable and stylish and reflect your character. Stainless steel is ideal, but a contemporary leather watch will do just fine
A formal watch should have a leather band and be higher-end. No need to spend thousands of dollars, but it should look classy, sophisticated, and minimalist. If you want to go really high end and the watch is over $35,000, negotiate the price and you can almost always get at least 30% off.
Sport watches: self explanatory
pocket watch: Keep it in the pocket of you grandfather's coat and store it in the attic.