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Think of it this way- the first $100 you spend on a pair of boots gives you 85% of utility/satisfaction you could ever get out of a pair of boots, and for most people, that's good enough!
The next $100 you spend (now $200) gives you 10% more, and now you've captured 95% of the potential satisfaction.
The next $100 (now $300) is only going to be spent by a person who demands the highest quality, with little compromise, from a well-known, and trusted brand (such as Oak Street boot makers). This gets you up to 98% of utility/satsifaction you could ever get.
To get to 100% on anything, the price starts going up exponentially, to the point where for the vast majority of people it simply isn't practical and/or they aren't obsessed enough to spend a grand on a pair of leather boots.
Bottom line- if boots aren't that important to you, then there's no answer anyone can give that would justify buying $400 boots, you can find great boots for ~$150 that will serve you well, and be almost as good as these boots. However, for some, that tiny margin of improvement is worth paying potentially hundreds of dollars for- and precisely speaking, it's higher quality materials, better craftsmanship, and a brand known for excellence in product & customer service.
Those are are main reasons
Since Doc Martens has a pretty wide variety, let's assume we're going with a median priced boot of ~$130-150.
- Doc Marten boot will likely be made in china, almost always machine made in large part. Oak Street boots are ALL hand-made in the USA- this craftsmanship does have value to people in and of itself, it may not for you.
- Oak Street materials are simply better sourced, almost all boots made of Horween Chromexcel leather, which is an extremely high quality, expensive material. It's going to look better, age better, and it's going to feel better when you wear them. This isn't to say Doc Martens use low quality material, it's just to say it's objectively not as high of quality, and it's up to you to decide if that's worth an astronomically higher price.
- I said I'd ignore aesthetics, but frankly Oak Street is just a less generic, generally more professional looking boot. It's my opinion, but I it's hard to argue against it- for example, I would wear these Oak street boots to my office with Jeans on Friday, but I wouldn't do this with any pair of Doc Martens I've seen.
Again, for most people, getting that last 5-10% of satisfaction is not worth 2-3x the cost- it really isn't and I get that. For a young(ish) professional like me, with a good job, and no kids, it's not something to sweat over- if I like it more and want it, it's what I'll get, and that's the market this kind of thing is for.
The last $100. What exactly is done to the boot that brings the 'potential satisfaction' from 95% to 98%?
edit: to be fair, JoeJoePotato did preface with "ignore subjective aesthetic preferences here". But still.
Take the Arthur model (http://www.drmartens.com/us/p/originals-boots-boanil-brush-arthur) of DrM at an MSRP of $250, which is almost in a 'dress-shoe' version of a boot: THE BOOT IS MADE IN DR. MARTENS' ORIGINAL NORTHAMPTONSHIRE FACTORY BY HAND, INCLUDING HAND-POLISHING. Etc etc.
So really that was a long winded way of saying it is a branding thing. Horween carries a price (although not all Horween is created equally) and a name/quality recognition, in much the same way as things are in the automatic Watch market. Brands like Rolex and Omega (while exquisitely made) fetch a far greater price than Seiko or Hamilton which are a far greater value.
Personally speaking I have not gotten my hands on a pair of Oak Streets yet but this drop will change that. I will say this about why I think the increased price on certain boots are well worth it; When I got my first pair of Alden boots after wearing a pair of Dr's for a long time I was stunned by the difference in quality. It wasn't even close in terms of build, comfort, leather, etc... Alden was heads and shoulders (in my opinion) the superior boots. Now whether or not a person feels that difference is worth the 4-500& difference is totally subjective. I am very interested to see where these Oak Streets stack up in my collection and I am assuming they will be somewhere around my Wolverine 1000 Mile Evans in terms of quality but I will give my honest opinion.