I’ve got some shoes that were around $150, a pair of heels and a pair of Tredairs. And my official “Texas Crew” jacket was $150 but totally worth it as it’s Gortex and I still wear it a lot. Truthfully, I usually wear “expensive” (for me, over $50) shoes with clothes from Target and Old Navy.
Ironically, the most expensive bit of clothing I wear was also the cheapest. My boots had to be hand-made and cost well over £400 - call it $800 at current exchange rates. Fortunately, work paid for them. 
Probably my tennis shoes. Although I got them free from my cousin, they cost him about $50. If it weren’t those, it’d be a pair of jeans at around ~$25.
As long as it fits and isn’t stained, I don’t care about clothes and would never pay more than $100 on something other than a suit.
While I can’t wear it anymore (it was a graduation gift), I have a double breasted linen Versace suit that was IIRC, $1700 new. It does still occupy a place of honour in my closet.
I paid $90 for a scoop-necked top with a Princess waist. It’s gorgeous and it’s lasted me several years.
Uhm. thinkety
Would have to be my favorite pair of boots - 11 inch harness boots from a well-known SF store for approx $130 plus tax. Got them in uni, wear them occasionally and take good care of them.
Black greatcoat when I was facing up to my first Seattle winter. :eek: Ran about… $100, I think. Had to get it retailored so I wasn’t swimming in it, which was another wad o’ cash.
Then my everyday Fluevogs, which I got off ebay for $70, about half retail price.
On the other hand, I wear clothes until they’re falling to bits, and shop about that often, too…
lizardling Stomp around town in them? 
After spending a couple days trying to find an appropriate and reasonably priced dress to wear to my cousin’s black tie wedding last year, I finally said “fuck this shit, I don’t care how much the dress costs, as long as it fits and is flattering.”
And thus I ended up with a $175 Jones New York black floor length dress. Anyone got an excuse for me to wear it again?
Yeah, I didn’t think so.
My Calvin Klein black wool winter coat. I love it and it’ll be stylish for years and years. So that makes the price absolutely reasonable if you calculate it on a cost-per-day-worn basis.
Right?
Well, I’ll be.
Somewhere around $500.
I bought a WWII Historical Horsehide A-2 Jacket a few years ago from the linked site. For a few bucks more, they allowed me to ask for some customizations. In fact, they made my jacket to order, shipped it so I could try it on, and allowed me the option of returning it if the sizing wasn’t just right so that they could make me another – at no extra cost. Nice place, and I really like this jacket.
I like the cut and feel of good quality suits. I spent about $2,500 on a couple of Hugo Boss suits, together with assorted ties and shirts a couple of weeks ago.
Probably the suit i got married in. It’s a Donna Karan wool suit for which i paid about $225 in the San Francisco Loehman’s store.
Most expensive things that i wear with any real regularity?
A pair of Ecco leather boots, also purchased in SF: $165 at the Ecco store
A Tommy Hilfiger brown wool overcoat: $130 at Marshall’s
I don’t usually pay more than $70 for a shirt, and i’ve bought plenty of decent shirts for well under half that. It’s good to wait for sales. As for pants, i spend most of my time in jeans—Levis or Calvin Kleins, mainly black—that come in under $40.
Couple of answers to this…
Single most expensive purchase of clothing? Lady Chance’s wedding dress: somewhere around $800 and currently residing in the attic on a dress form (because all attics should have wedding dresses on forms, right?)
Single most expensive day-to-day item? My current $450 leather jacket. It weighs about 25 pounds. I like 'em thick.
Most expensive outfit? My ren faire costume. Blousy shirt, leggings, tights, cloak, belt, purse, sandals (or boots), hat, cloak - about $1500.
Does special purpose gear count as clothing? I have a diving drysuit, immersion (survival) suit, floater worksuit, down parka & pants for extreme temperatures at altitude, a down parka for arctic environments, etc. Some of this stuff is well into the thousands of dollars, but I wouldn’t exactly call it everyday clothing.
If you count my two-piece motorcycle leathers as one suit, then it’s ~$700. I also paid $300 for my tux, and about that for my suit (reminds me, I really need a new one).
Ecko Unltd jacket for about 150 dollars eventhough it was a generous gift on my Birthday and a black T-Shirt that I had JEREMIAH (My Name) airbrushed on the total price for that was about 40 dollars, come on a 40 dollar t shirt is expensive.
Lessee…
Tuxedo–probably a couple thousand all told (with shirt, vest, etc.) (yes, ladies, I own a tux)
Suit–$900?
Raincoat–$700?
Glasses–$800?
Filson coat–$250-350 (I’ve got 3 different kinds)
Birkenstocks–$200-ish
Various shirts, belts, jeans, etc.–$50-250
Going to a fine restaurant looking like a lumberjack but getting compliments from the few people who actually recognize what you’re wearing–priceless
I have a few Armani suits, a Ferre suit and some tailored ones. They were 'spensive - but at the time it seemed to make sense. Now, I think spending more than say 600 bucks on a suit is kinda silly.
Then again, these suits look good .
$1300 St. John suit. It’s a classic.
Susan