Who are your favorite vintage clothing companies and independent craftsmen

I like the idea and I think it can be successful.
But I am with E to a point as well.

I have said it before and I'll say it again, this is a builders market, not a buyers market.
What that means for you is that you have a very savvy customer that likes to save dimes here and there.

2 Examples:

1)
Sitting on my couch last night talking about bikes and my buddy says: "I hate buying things from stores because I know full well for quality stuff I can go straight to the people that make it cheaper" This is a big problem you will face, because most of the small manufacturers that you would push make their money by selling their wares themselves, and not by wholesaling to bigger companies or outlets. Most will try to keep their markup as low as possible to keep their sales volume up, so in the end when they end up wholesaling to you, you have to mark up their markup to make any money and the customer can get it cheaper from them. The alternative it for them to add markup as well, however when your site is not sufficiently large to demand the prices the small business is shooting himself in the foot.

The solution to this problem is that you have to be large enough, with enough products offered that you are the go to place for such goods, and then the customer does't know or care to search out a better price.

2)Your customer is smarter than the average customer. You're not selling to housewives who are looking for something pretty. You're selling to guys that spend a lot of time building stuff, searching out deals, and stretching their dollar. This can be an advantage or a disadvantage.

For example I just bought a few master cylinders from china because I wanted some cheap ones sitting around for builds. 22.50 a pop. I just happened to be on another site looking at PMA kits and noticed that a well known retailer sells the exact same master for 65.95. A little more looking and all the major retailers sell this same master, anywhere from 100-600% markup. My point here is that you are unlikely to find many buyers who are unwilling to search around a little bit unless you get to sufficient size like dime city whose prices are only okay, but you can get EVERYTHING from them so why bother wasting your time looking elsewhere?

On the advantage side, this is a culture/people who appreciate quality and in my experience are willing to pay for it, so in that vein you are in good shape. I happen to believe that the trends in production and purchasing are tending toward more handmade high quality items after the last decade or so with the influx of shit quality china made stuff.

Anyway, my rambling overarching theme here is "Know thy customer" and cater your offerings to the customer
 
Gotta give some love to my brother and his leather goods! He makes anything and everything.. and we're both obsessively detail oriented.
I'll post more pics next time I visit, here's a planner he made for me and the first purse he ever made (for mom).
 

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