Cadillac (Omega) Problem

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So here’s my “problem”. I have a Hesalite Speedmaster Pro on the fabric strap with the deployant clasp. I love everything about it. The vintage look, the comfort, the history, all of it. All my other watches are sport watches and I’m in the market for something a little dressier. I really like the look of the Hesalite Pro on the bracelet. Classic and dressy enough for my needs. I could just buy a bracelet and switch between the bracelet and the strap on my current Speedy but I don’t feel like doing that every time I want to wear a dressier version. I could buy the sapphire sandwich on the bracelet and then I’d have both the Hesalite and the sapphire version but I prefer the brushed bracelet on the Hesalite version.

I’m not wealthy but I can afford to buy a new watch and it won’t be financially imprudent. However, just because I can doesn't mean I should. What does the forum think?

1. Just buy a new bracelet and switch it out when necessary.
2. Buy another Speedy Pro Hesalite on a bracelet.
3. Buy a Speedy Pro sapphire sandwich on a bracelet.

I’m leaning towards buying a second Speedy Pro. Probably the sapphire to expand my Speedmaster collection to a different model. The question is am I being unnecessarily spendy when simply buying a bracelet will fix what I’m trying to accomplish? Yeah, I know. Buying another watch (or car or gun or bicycle) is always the correct answer. However, I’ve bought and sold enough watches over the years to know that what seems like the perfect addition could end up being a regret. I doubt that will happen because, after all, we’re talking about Speedmasters. Still…….
 
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I think most people would consider a dress watch to be something relatively small and thin on a leather strap.

But, then, such categories don’t matter much anymore, at least not to most people. If you like a braceleted speedy as a dress watch, no one can stop you.

I’d just buy a good aftermarket bracelet with quick release. Buying a second speedy just because you like the bracelet look seems like a pretty extreme choice.

So many other brands, so many other watches—including some really stunning dress watches for less than the price of a speedy…
 
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Buy a good springbar tweezers--Bergeon 7825--to make bracelet/strap swapping easier.
 
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How about sell your current Speedy, buy a '90's hesalite tritium and the current sapphire on bracelet, that would be win/win in my book.
 
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Shoulder-devil here again. I'm just saying: for pretty much the same cost as (and possibly even less than) a sapphire braceleted speedy, you could get into some serious "real" dress watch, preowned. I'm talking a Vacheron Fifty-Six or a Pamigiani Tonda 1950. Talk about one hell of a two-watch collection: your hesalite speedy and a VC56?

And a huge portion of the JLC world is at your fingertips, if you prefer not to go preowned.

You mention having a bunch of sports watches and wanting something "dressier." It just doesn't seem like a second, nearly identical, speedmaster--on a bracelet---is the answer. It's like someone who owns a bunch of motorcycles and is in the mood to buy an SUV is asking if we think he should therefore pick up a new Harley. But maybe I'm misunderstanding something here.
 
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If you want a new speedy on a bracelet, and it doesn't matter financially, then I say go ahead and do it.
 
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Can you share pics of your current speedy on the fabric strap? I don’t think a metal bracelet necessarily makes a watch dressier.
 
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Buy a good springbar tweezers--Bergeon 7825--to make bracelet/strap swapping easier.
This!
 
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Thanks for all the suggestions. I haven’t made up my mind yet but the one constant is it will be an Omega. It’s my favorite brand by far and nothing else from any other brand appeals to me.
 
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Congratulations! I can empathize with the situation you were in. I love my Speedy on a rubber strap but on work days, it's too casual. Other sporty watches I prefer the bracelet. My eventual solution (after a lot of buying and flipping due to redundancy) was the same as yours: a selection of sports watches and another of dress ones.

Wear your Deville in good health!
 
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Bracelets are less dressy than straps, IMO. Your new watch is much closer to being a dress watch than a Speedmaster would ever be.