persco_

They look great on you. On Christophe... not so much. I love the fabric and colour on these.

Lovely. I've been searching for a 39mm OP black stick for a couple of months, but the Rolex market is so screwy right now. I've decided to wait for the madness to calm down (if it ever does). I got a PAM 915 instead. But I do love that OP black dial. So simple and beautiful.

I got very Cottle-curious a few months ago. But the more I delved into the brand the more precious they seemed and thus not worth it (to me personally) for the premium being sought. Then I walked away. This is where I think William at Tender has struck a good balance between what you framed as whimsy mixed with attention to detail that just somehow retains an authenticity (probably misquoting you).

Agreed. Naoki is amazing.

Looks like the work Dr. Sole? They look great.

Are those the Vincent's you had rebuilt? They look amazingly different. Would be great to see those up a bit closer...

I love them, but do wish they were bigger.

I'd take a look at vintage Omega Seamasters -- like the pie pan dials. They're around the size you're interested in (maybe a touch bigger at 34mm). You could also pick up a small vintage Rolex for a good price (relative to the prices for larger sport models). Search Watchrecon (link above) and you'll get a good idea of what's for sale and where. Omega Forums is a good place to get started on what to look for. The vintage market is also filled with a lot of frankenwatches.

I've never heard of Vague so I don't know where they might be made, but Orient and Seiko (Japanese companies) both make lower-priced watches for third-parties (but likely not actually made in Japan). 30mm is on the small side for a watch by modern standards, so the options are going to be a little limited. I think William at Tender has quite a good collection of mechanicals in this style-(ish?) around the size you're looking for. https://www.tenderstores.com/product-category/watches/ Otherwise, I'd seek out vintage where you will have a very good range of choice for good prices in watches of that diameter. Try also taking a look at Watchrecon for what's available in the secondary market.

This is what often puts me off FW when looking at their pants. Though the 1022008's are great, there's usually too many additional details like straps and buttons at the hem, or extra pockets randomly placed on the thigh. I get they're making these items based on historical specimens, but I find them a little too busy.

So I see @BrownMetallic's post with a super nice pair of old Dayton Drivers a few days ago. I've wanted a pair for a long time. I used to wear Dayton boots (not the drivers) in the 90s, I think I went through three pairs. The Dayton story is sad given what's become of the company now. And they haven't made these for several years. But by some weird turn, I ran across a pair in my size for sale here in Canada in a Kijiji ad. They arrived today and turns out they've barely been worn. I love them. Paid $100 CAD.

Killer Dayton Drivers. I wish they still made them...

Not sure any of this will help you. I own a couple pairs of Carminas, as well as Church's and three pairs of Nick's (which are also based in Spokane, same basic design, essentially equivalent to Whites and split off from Whites in the 1960s). The quality of construction is very high but not highly finished, if that makes sense. Carminas and Church's and the Japanese brands are really precise in finishing. Nicks/Whites use thicker leather and heavy duty stitching but things aren't perfectly cut or stitched. They're well made, but not finely made. My Church's are very very well made and finely at that. But they feel no more robust than my Nick's Comstocks. But the Comstocks are rougher in construction -- not lined, stitching around the welt is a little uneven, the edges are unfinished, etc. But they are exceptionally 'heavy duty' hand-made, old-school construction.

Tender 132, 132X or 136. Very wide leg.