Oak and Oscar Disappointment

I have nothing to add. I agree with you. There is nothing in their catalog that would make me want to spend the money. It is all perfectly nice and fine but not at that price.

I hadn't heard of the brand before now, so please excuse my ignorance. I just checked out their offerings and I have agree, but I would even suggest a lower price. For me and if I was buying just for the made in the USA factor I would be looking at Vaer myself. Granted in doesn't have a Swiss movement, but they do have others that do and I saw nothing over 1K.

For me it would be this one at $529 on a bracelet 💯

That's why i have to see a watch in person. The other chicago based watch companies that come to mind are Haim, using the seagull chronograph movement, a bit too expensive for me,, but still cool. They were at the windup even  too. And Wolf Point, of which I'm no fan. 

I have a couple of friends that have and love them.  I was really tempted by the new gmt but I could get a Sinn 105 utc for the same money.  I am hoping to see one in person soon so I will reserve my judgement but I feel like I might be underwhelmed. 

Grabbed a Humboldt used at Topper for less than $1000, which to me is about right.  The watch itself is very cool and given I lived a block away from Humboldt Park, the 4 Star rotor driven watch was a no brainer.

That said, the bracelet felt like it belonged on a $300 Seiko, so I immediately removed for a custom strap. As a watch itself, I don’t think the quality is any less or better than a Sinn 104 (own both), which is priced similarly. 

I honestly don’t think people are cross shopping O&O with Tudor or IWC. The O&O customer is looking at Oris, Monta, and others in the $1500 range. If one expecting Tudor or IWC level, they should just buy those brands as (outside of Monta), that level of quality isn’t happening under $3k. 

I like their watches just fine. As a huge baseball fan, I'm always on the lookout for their Ashland.

Out of curiosity, did you get that in the last couple weeks?

Nodus is a good American brand too.

I’ve had it for a couple years and picked it up around the same time I found a 104 on eBay.

I believe, though it may have changed, they use Walca (Private label watch maker) to help them with the production of their watches. Like most (almost all) micro brands that use private labels, or even the few that try to go at it alone, the watch is as good as they are willing to pay for parts and supplies while meeting a specific margin threshold. IE, likely why the bracelet on mine did nothing for me given the cost.

Keep an eye on Toppers, they frequently get O&O pieces, which buying preowned helps.

Yeah, I check Toppers once a week, but they recently had the watch you said you picked up and I was trying to get it for a grand by trading a couple watches. They wouldn't go below their asking.  Recently, I'm finding it difficult to deal with them, unfortunately. 

Interesting, I wonder if it is due to their move?  I imagine their margin on sub $2000 watches is razor thin. They are still higher than eBay price wise, even with discounts, but I like that I can trust them and pick up the phone or shoot them a message.

Yeah, I don't know.  It started before that.  Having said that, they are probably better than most and I still recommend them.

Point taken. Monta did seem better made to me from my short time with the watches at Windup. 
 

I think the Longines Spirit could be something for someone to target in a price range above Hamilton but below IWC and Tudor. The Spirit has a field watch vibe in many ways and is well constructed if the proportions work for you. I’m not crazy about how the numbers on the Spirit dial look in person, but it seems like a quality watch and gets a lot of positive reviews from owners. 

It’s a nice watch for certain. The beauty of many of the micro brands is there is a ton in that range, while still competing with some of the big names. I think I’d gravitate to the Hamilton if comparing the two aesthetically. 

https://www.hamiltonwatch.com/en-us/h76205530-khaki-aviation-pilot-pioneer.html

I've never found a watch that I didn't find aesthetically interesting in pictures to all of a sudden become interesting when handling it in real life. I've definitely come to appreciate aspects of watches more when handling them in person, but I'm not surprised you didn't have any aesthetic revelations once you got to play with one in real life.   

I've owned a few Oak & Oscar watches (currently own a Humboldt GMT) and used to live a five minute walk from their office.  Whenever I see anybody post something similar about any brand, I do like to have a better idea about what kind of watches they currently own.  

I've had the good fortune of handling a lot of different microbrands in the $500-$2000.  I've only ran into a couple that I thought were just bad, but mostly I just think of them as different levels of good, but I do see distinct differences in look and feel between ones at $700 and ones at $1500. For instance, the Nodus watches I've handled are nice, but they feel to me like they should be cheaper than an Oak & Oscar or a Monta.  Whether one feels the relative price difference is worth it is a different and fair question, but is mostly a subjective one.

Comparing a Monta to an O&O is a fair thing to do.  They both offer GMT model on a bracelet with a microadjust clasp. They are both priced about the same.  The Monta has more intricate finishing as its a mix of brushed and polished whereas the O&O is all brushed (and fairly well done IMO). The finishing of each watch seems to be right for the vibe of the watch.  The O&O comes with an extra NATO Strap, a locally handmade watch wallet and strap adjustment tool, while the Monta comes in a more typical box (and maybe something else?).

IME, they are both superbly built, but the mixed finishing on the Monta definitely comes off as nicer in person, especially if you want a more elegant vibe.  Does that mean that maybe the Monta should be more expensive than the O&O (or conversely the O&O should be lower cost), maybe? But then again the O&O has an anti-magnetic and anti-shock treatment more befitting the tool watch nature of its finish. Maybe between the extra goodies the O&O comes with and the additional durability features it shares help even out the price a bit? 

The lugs of most, if not all, Hamilton watches just doesn't work for me.

I'm surprised by the bracelet comment. I had a Willard last year and a Turtle before that and the bracelet on my Humboldt GMT is way nicer.  Of course, the Humboldt GMT has their new microadjust clasp and I would assume yours does not, but other than the clasp I don't believe they've made any changes to the bracelet since it was originally introduced.

That said, I find these to be great NATO watches, so after the first week on the bracelet it's been living on one of the approximately million 20mm NATOs I own.

Granted I generally feel all watches are too expensive, but I don't feel like your standard IWC Mark XVIII is appreciably nicer, if at all, than a time & date to an O&O Olmsted.  I've owned both a Mark XVIII and an older O&O at the same time. The IWC  was preowned and over double the price I paid for the O&O (not to mention almost 3x the retail price). If anything the IWC with the shortcuts they take using a movement too small for the watch with its floating in the middle of nowhere date (that was also unmatched) and flat, poorly lumed dial, comes off as super low effort. It's certainly a well made watch, with slighly more interesting finishing, but one is definitely paying a heavy amount for the name and the historic notoriety of their Mark series rather than any special level of quality.

I believe mine was their first bracelet as it is  at least 2-3 years old. Stamped metal, really light, just not a premium product. To your point, I had every intention on replacing it regardless, but it was slightly better than Seikos I’ve owned, but felt cheaper than a Zodiac SSW (a bracelet I dislike for other reasons).

I also don’t disagree with your comments on IWC. Comparing MK XVIII to, say, a Black Bay 58, or even basic 41, I don’t get it. It has a quality to it, the bracelet is awesome, well finished etc, but in my mind it is a $2500 watch.

I had a Nodus Sector and it was a great watch, I gifted it to a friend, which I sort of regret but don't. If that makes sense 😉

I've been curious about the Oak and Oscar brand.  Never handled or seen one in person.  It is disappointing to hear they didn't live up to your expectations.  I do think the design is nice but I always did wonder why they were priced so high compared to other microbrands.  I like microbrand watches generally because they tend to be great values for price paid.  They usually punch above their weight, but I guess that's not always the case.  

I agree 100%. They make a decent product, but not worth the price tag. Brand at windup that I liked the quality and design were Farer, Formex (bought one), Oris (Also bought one), Junghans, William Wood, Chris Ward, Monta and this super new brand Foliot.

Astor and Banks is also Chicago and have nice watches

Know I’m a little late to the party here, but have you had a chance to come back around and get hands on again? I love my Humboldt GMT and would definitely like to get more hands on with the brand. Would be interested to see if you’ve come back around?

I haven't seen them again since last year at Windup in Chicago. Unfortunately, I can't go again this year. I just don't think this brand is for me style-wise but I also don't know why you would choose this brand over a more established brand like Hamilton or Seiko. You pay more, but I don't think you get more unless you just want something that less people will be wearing.