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

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.

Okay, let's address this in a slightly different manner.  Instead of specifying the country of origin (unless that's of particular importance to you), let's begin with a list of your requirements.  Swiss watches are wildly overpriced for their quality, when compared to watches available from other countries.

 

Metal case
Leather band
Versatile style
Roman numerals
Low cost

 

That's a good start, but let's see if we can narrow it down just a bit.

 

Do you have a preferred shape for the case, i.e. round, square, tonneau, etc?  Regular or fancy lugs?  
Simple hands, or something fancy?  
Do you like fancy details, or plain design?  
What color for the dial?  
And, do you want the mechanism (insides) to be mechanical or quartz?

 

Let's start with the metal.  I suggest solid.  I never recommend plating, whether gold or black IP, because it eventually wears off and looks bad.  In your price range, that means stainless steel is most likely, though a ceramic case might be possible.

 

As for the bands, so long as the lugs are a standard size and design, yes the bands can be easily interchanged whenever you feel like it.  The bands can be purchased anywhere, in stores ranging from WalMart, to jewelry stores, to custom shops.

 

As for the style, that has nothing to do with the cost.  Some of the best looking watches I've seen are the cheapest, and some of the ugliest are the most expensive.  If you like the $200 Tissot, and it fills your requirements, then put it on your list.  Tissot is a very good brand, on the low end.  If you're willing to expand beyond only Swiss, though, Seiko is a top tier brand and can be purchased at a comparative bargain, and Orient is a sleeper brand that is very well respected by those in the know...their Mako is positively amazing.

 

Another option that would work within your budget would be to get a used watch, or if you prefer a different term, vintage.  This will get you a MUCH better watch, and still stay within your budget.  

 

Watches are, basically, jewelry, and are priced not based on their material value, but on their artistry, finishing, and design.  And their branding...some brands are more desirable than others.  For example, the Swatch group owns both Swatch and Omega...the mechanism inside (ETA 2824 automatic) is identical between some of their models, and yet the Swatch may sell for $150 while the Omega would sell for $1500, the primary differences being branding and detail finishing.

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