Once a week or so, I would go on Amazon and search for certain brands I liked in my size. Once every few months or so, I'd find a shoe I liked in my size that was absurdly cheap. (Eg. a solid Allen Edmonds loafer with a leather sole for $33 bucks).

Years ago, there were tons of companies using Amazon's search feature in this manner (but automated) to help people find deals, so Amazon fucked with their search to make this strategy not work as well.

Doesnt work any more.

So, to answer your question, a pair of like $400 boots I copped for like $100 bucks.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47625360)

also have a pair of amazonian lizard luchesse's from the original san antonio factory. i got them on craigslist for $300 in like new condition, but no telling what they're "worth". the skin is illegal now. a comparable new pair would be like $1500.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47625367)

I got elevated. Now wear Peter Millar etc to work most days. Suits still come out a few times a year.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47627988)

don't remember cost. msrp was probably 650 or 850.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47625745)

Then I realized they suck (normal people wear rubber soles for a reason) and no one cares.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47626528)

At the $1,000 level I have Ferregamo tuxedo shoes and dress loafers. (I think the tux shoes were $950 and the dress shoes were $800 or so.) I bought both of these a few years ago before Ferregamo went all fruity. I have a black tie event at least every month so it was worth it to get tux shoes I can actually walk in. (I don't normally condone spending a lot on patent leather tuxedo shoes.)

To be honest, though, the most "expensive" shoes I buy are Tod's gommini loafers. They are $545 MRSP, though I won't buy them unless they are $400 or less through department store sales, markdowns, etc. But the motherfuckers wear out in like two months. They are really comfortable and I love the way they look, but christ they are built like a sheepskin condom.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47626569)

Tricker’s — I think the Country Shoe? — also bought 15 years ago. They’re $745 now. They are very nice but super stiff.

I wear sneakers to work 99% of the time now. Back when I wore suits I wore standard $300-400 Allens Edmond.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47626612)

Otherwise just a bunch of pairs of AEs from when I was in biglaw bought at between $200-$300. They kina suck. Literally have had the black park avenues since 2012 and they still don't really feel broken in whenever i wear them.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47626625)

dress shoes I have a few pairs of BB Peal & Cos that I don't think they carry any more. They used to retail for $500+ but would go on sale for less than half that, which was when I would cop

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47627963)

i have multiple $300-400 shoes/boots/loafers/sneakers that i acquired on sale over the years, but mostly just wear adidas or nb sneakers to work these days.

(http://www.autoadmit.com/thread.php?thread_id=5523640&forum_id=2#47628003)