I am going to buy my first watch. I was wondering if someone can offer me some suggestions on a good, stylish, and versatile watch.

I am interested in the Swiss watches and would like to have a leather banded one. A watch with Roman numerals is a big plus.

I am trying to decide whether to get a black leather band or a brown. I wear black loafers often and it seems that the watch should match the shoes. 

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I like Swiss watches, but that doesn't narrow it down, much.

 

It sounds like you want a dressy watch with standard lugs, which can take a leather band.  That's easy.  Roman numerals are usually either applied or painted on, and can make a huge design impact.  The color of the band is immaterial, as the bands are easily interchangeable and relatively inexpensive.  In fact, I usually recommend getting the metal bracelet, and changing it out as you see fit.  Gives you the most options, that way.

 

So, what color do you want the metal to be?  What shape for the case?  What level of detail?  And I'm sorry to be so crass, but what is your budget?

 

Without more details, I'll recommend the IWC Portofino, which is an exquisite timepiece.  The dial is simple, and in this version the case is stainless.  MSRP is just shy of $5000US.

He did specify Swiss...the Emporio Armani watches I've seen use Asian sourced movements.

 

Cool watches, though.  I looked at a few, at the Fossil outlet store.

Because I am a jerk and cannot resist, I say your first watch should look like this:

Let him get a regular watch, first, before you get him started in specialty collections. Some of those Mickey Mouse watches are frighteningly expensive.

 

Wish I still had my old Snoopy and the Red Baron watch.

Don't we all, man.  Don't we all.

my dad had one of those to match his mickey mouse tattoo

I guess one of these days I should take a picture of my saved watch.  A childrens wind up, original Star Wars featuring R2D2 and C3P0 with stars in the background, the band is a light blue.

My squadron's weapons instructor (highly trained, combat veteran, tactics guru) wears a Mickey Mouse watch...and you thought military pilots wore Breitlings and Rolexes.

I work with pilots everyday. they are the biggest group of fratboys you will ever see. yeah I can imagine many of my jet jockeys in my squadron wearing that

Mine had a black leather band.  Just saying.

The angles his arms go into (especially at times such as 'quarter to ten') are kind of sinister when you think about it. It's like Mickey Mouse is going through an endless cycle of Medieval-esque torture...

@Chuck

I am open to any type of metal, but want a leather band. I presume if I buy a watch with a black band I can easily replace the band with a brown one? My price range is not too high, $200-$500 though $500 would be pushing it. I am not a watch fanatic, but want a nice one to carry when I go out for both formal and casual events. If the watch has Roman numerals on every number that would be a huge plus.

So far I've been looking into the Tissot watches. Some watches look terrific but when they're priced below $200 I get suspicious. I don't want to buy something that will look cheap and tacky.

The Emperio Armani watch looks nice though.

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