26mm two-tone Rolex outdated?

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I have the 31 and I think it's the new classic size. Interestingly, it was an orphan size (low sales) not long ago, when it was referred to as the "boy's" watch size. So you're right, things change.

But you don't have to despair: It does have some trade in value, if you might want to upsize. I would advise sticking with 31 if you do.
Agree.
I have a 31 in rose/ss two tone and I love it. I also have a 36 and enjoy that for sportier outfits. I also had a 34 but sold it as it wasn't getting much wear. My favorite size is the 31.

I chose rose TT instead of yellow gold TT because it was more feminine and more modern, but the YG will always be a classic and i would wear 26 if I could pull it off.

Here's my 31. IMG_20180708_180914.jpeg
 
Agree.
I have a 31 in rose/ss two tone and I love it. I also have a 36 and enjoy that for sportier outfits. I also had a 34 but sold it as it wasn't getting much wear. My favorite size is the 31.

I chose rose TT instead of yellow gold TT because it was more feminine and more modern, but the YG will always be a classic and i would wear 26 if I could pull it off.

Here's my 31. View attachment 4125931

Love this
 
Yes. It’s dated looking. Rolex even discontinued it.

Most ladies who wear it I would say are not fashion forward so it depends on your style and how fashionable you want to look. (I know, the claws are coming out now, but it’s my opinion). Or the 26mm is worn because they have had it for a long time and because it was a “Rolex” and expensive, they don’t want to part with it, even though it is a dated piece.

I would get a larger Rolex if I were you, 31mm or 36mm (I wear a 40mm).

For formal events, ladies do not usually wear watches with evening gowns.

By the way, I own several Rolexes including a 26mm TT Datejust (my first Rolex). I am actually thinking of selling it as I won’t ever wear that watch again.

Just my honest thoughts I want to share.
 
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Totally agree. Of course a 26 or 28 can look wonderful on a slim wrist. Larger could look fine, too but a 40 could look ridiculous on the same wrist. Funny, I know some women who bought a 26 or 28 when they were younger and slimmer and they have “outgrown” them and they look too small now and I would agree they need to update the size.
 
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26mm is beautiful if it has sentimental value and as long as you love it. Trends come and go, if you no longer love it, let it go because you won’t love it even if small watch comes back in fashion.

Personally I disagree that small watch needs to go on a skinny wrist and similar for big. I have a tiny wrist and looove a big watch but for the classic datejust I would not go bigger than 31 but would happily wear men’s sports gmt/sub/Daytona which is 40 (and received a lot of compliments wearing them). Personally I would not pick small watch (also why I’m not a fan of some of the Cartier) for something as classic as Rolex simply because I don’t want to struggle to tell the time when my eyesight gets worse when I get older? (LOL)
 
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I have always had a 26 mm for the past 29 years, of one combination or another. But now, at 61, when I wear my TT 26, white dial, Roman numerals, I can't usually read the date unless I am in very bright light, LOL. I still wear it when I want to be under the radar, as I also have a Sub with date and a 36 SS Datejust with pink flower dial and diamond bezel...
 
No watch, either small or large, is going to "date" a person's look imho, unless you are pulling a pocket watch out of a waistcoat. Hairstyle, makeup, clothes and shoes are way more important and always grab my attention first. So, if your clothes, hair, and makeup are up to date and stylish, a smaller 26 mm watch won't doom your overall look one bit. So, I say wear your 26 mm Rolex, maybe stack a couple bracelets around it occasionally, and enjoy the heck out of it.
 
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