I've seen two problems when buying wingtip boots, though: 1) if affordable (like the $35 UO boot), they tend to rise up too high on the ankle, giving them a hiking boot rather than dress shoe feel, or 2) the boots are gorgeous but way too pricey for something you might need to wear in rain/mud/snow (AE Dalton, I'm talking to you).
Florsheim, however, seems to have struck just the right balance, getting lots of brogue detailing in a hightop-high boot. In the Florsheim Limited line, there's the Gaffney Boot in chestnut, $140 through Zappos but can be had for about $100 with code NEXT20 on Florsheim.com website. Rates fives stars on both sites. Yes, it has a lug sole but the chestnut is perfectly colored and the uppers polish up nice.
Then there's the major upgrade: the Brogue Boot in the "Florsheim by Duckie Brown" line. Normally $475, you can scrounge one up for $200 on eBay and on Neiman Marcus and LastCall - but who knows what colors and sizes will be available.
Luckily, Gilt.com is running an insane deal right now on the Broken-In Brogue Boot in Brown - only $79. Yeah, $400 off - making it even cheaper than the Gaffney for a boot that's leather-soled, Goodyear welted, and made with Horween leather. Both the Gaffney and Brogue Boot run large and wide by a half-size, so be sure to size down when you buy.