If you travel internationally then you can probably save dollars depending on location and currency exchange rate at the time. As far as being duty kosher, well, that is up to you. Frankly the Customs folks don't want to get involved in figuring duty on someones new Omega bought overseas. They don't want to hassle looking it up in their customs book figuring origin, number of jewels, case material, kind of strap, etc. in order to figure some duty. I have a sister-in-law who used to work Customs at JFK airport, they were NOT looking for watches, they were looking for cash and drugs. They had one agent who always went after people who looked like they had new watches on, they told her to stop it, it was diverting their attention to more important aspects of their job. One time I was returning from the UK and got behind a woman who declared some cashmere sweaters at Newark airport. The Customs agent said, 'I have to charge you because you declared them, but next time just pack them in your luggage and forget about it'. So put it into context, if it makes you feel better declaring it do it, otherwise wear it and enjoy it. Just my 2 cents from experience. It's a similar thing with out of state sales, you are supposed to declare it to your state of residence and pay the relevant tax, but no one does it. But since the Supreme Court has now ruled that states can force out of state retailers to charge sales tax that window for savings is closing.
If you are new to the game I'd buy it from an AD even if you have to pay a little more, peace of mind is important and you don't have to worry about the grey market. Once you get more experienced you can go that route and save real money.
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