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I appreciate the honest assessment. My ability to accurately judge any aesthetic option is very limited.
Surely. While I'm no fashionista I do have a design background... here's my college education in a nut shell:
1. There is no wrong.
2. The mind knows what's pleasing, we all like symmetry.
3. Breaking rules in an intelligent manner is good design.

Now above said and looking at that pairing in thinking stripes and plaids.
The rule is never, they don't go together... however it's trendy for years now if done "right".

This example comes to mind I think because the stripes on the band are bothering me with the tick marks on the bezel from noon to three.

If you're bored, try centering those bezel marks from 11 to 1 and lmk what you think. Better yet, snap a pic!

I think a solid contrast color would be striking on that watch personally.

Below is my daily tag. It's the nicest watch I own and I enjoy it from dress to casual including working under the car... others in my collection are a couple Tissot from the 90s, and a few vintage from the 40s 50s maybe... most notably a Jules Jergensen gold watch from my late uncle.
 

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Surely. While I'm no fashionista I do have a design background... here's my college education in a nut shell:
1. There is no wrong.
2. The mind knows what's pleasing, we all like symmetry.
3. Breaking rules in an intelligent manner is good design.

Now above said and looking at that pairing in thinking stripes and plaids.
The rule is never, they don't go together... however it's trendy for years now if done "right".

This example comes to mind I think because the stripes on the band are bothering me with the tick marks on the bezel from noon to three.

If you're bored, try centering those bezel marks from 11 to 1 and lmk what you think. Better yet, snap a pic!

I think a solid contrast color would be striking on that watch personally.

Below is my daily tag. It's the nicest watch I own and I enjoy it from dress to casual including working under the car... others in my collection are a couple Tissot from the 90s, and a few vintage from the 40s 50s maybe... most notably a Jules Jergensen gold watch from my late uncle.
Interesting take, I enjoyed reading.

Like ByMyBeard I would wear that combination of strap + watch, mostly because I enjoy this style of strap and having fun with them. But I wound not be very satisfied with it. My sense off balance is more about the mix of colors, how the main color of the strap is off-white while the dial markers are white (though they change in color because of lume). How the strap picks up the red second hand, leaving the dark blue stripes to almost pick up the black dial but it does not and is left hanging. If the strap did not have the blue stripes or if the blue stripes were black then it would work better and perhaps if the red stripe was thinner to better match the thickness of the second hand then it would start to be a very good match.

I have a dozen or so of these regimental straps and never found them ideal in terms of being a great match to any watch, something about the ribbed nature of the fabric, imprecise lines on the straps, sheen of the fabric, weight/thickness of the strap, means that they don't look great on most watches IMO. I think they work best with more basic dials and thin watches such as the Timex Weekender. Solid color Natos are easier to match and compete less against the dial, but I have come to accept that these straps are playful and just wear them for fun and do not try to find a perfect match.
 
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