The title pretty much says it all. What is the single most expensive piece of clothing you own/wear? FOr the purposes of this thread, clothing is shirts, pants, underwear, socks, jackets, hats, coats, mittens, skirts, shoes, dresses, suits (even though they are multiple pieces, they are usually bought together, so it counts as one item,) etc…
Things like watches and jewelery don’t count, there aren’t really clothing.
I don’t usually spend much money on clothing so shelling out $100 for my floor-length black velvet cloak was a big stretch for me but it was worth every penny.
I have a pair of Chanel slides that were $375. Cost more than my wedding dress…which is the next most expensive thing I’ve bought but was only $325.
My sneakers were something like $120. They’re good shoes and the pair before them lasted me all through high school, so these will hopefully last me through college.
I don’t know if this counts, but my most expensive item of clothing is probably one of my leather motorcycle jackets, which cost about $525.
If we’re talking everyday-type clothing, probably a leather aviator jacket I paid around $350 for.
I tend to spend a lot on jackets, but not nearly as much on basic stuff like jeans/shirts/etc.
I may be wrong about this, but I think it’s the sweater I made, for which I bought 80 dollars worth of wool, plus another $10 in buttons. It do have lots of leftover yarn of various colors in my stash, so you might want to deduct its value from the cost of the sweater, but it’s not like I could have made the sweater without buying those skeins, and it’s also not like I’ve made anything else out of them . . . yet.
Anyway once you add in the dubious value of my labor 
I’m pretty sure the most expensive piece of clothing I own.
Somewhat depressingly, by that same measure, I also have a $12+ pair of socks.
Probably my Doc Martens black and white spectator shoes. I paid $150 for them at Journeys back in early 1998, when they could have been considered “trendy” with the ska and swing music scenes going on. However, I’ve kept them clean and I only bust them out for special occasions (gigs, dates, concerts, parties, weddings, anything that involves dressing up at night) so they still look brand-new. One thing for sure, if I go out and I’m wearing those shoes, I always get tons of comments on them, and they’re sure to be the coolest shoes in the room. That retro two-tone wingtip/spectator look combined with the heavy “bouncing soles” and sturdy, rugged construction of Doc Martens boots makes them timeless, and they should never go out of style.
My gray double-breasted trench coat may have cost a bit more, but my parents helped with that one. Still looks bad-ass several years later, and it’s really warm and surprisingly soft too.
When I finished my Ph.D. I bought a suit from Brooks Brothers to go interviewing in. I also bought a Dooney and Bourke handbag and a few other things. The suit was about $400, 15 years ago and the bag was a couple more. I still have the suit and wore it two years ago when I interviewed for my present job.
I just purchased a North Face Met 5 Jacket that ran me $600. I do not consider myself materialistic at all, but I do like quality gear. I have an Orvis sport coat that ran me close to $500 as well. Thats about it I suppose.
It’s a toss-up in my closet - either my last suit or one of my down parkas. Couple hundred bucks, either way.
For the most expensive section of my closet, it would have to be my collection of Hawaiian shirts. I have 75+ shirts, all of them loud. 
My wedding dress was the most expensive item of clothing I ever purchased.
The second most expensive was a pair of Manolo Blahnik pumps. At least I get to wear those more than once! I’m not sure what possessed me to buy them, as you’d be hard pressed to find anything else in my closet I’d paid more than $50 for, but at least they’ll last me awhile.
I usually buy most of my stuff at consignment sales and ebay and the clearance racks but I broke down and purchased a pure cashmere cardigan from j jill when I lost my last full time gig. The folks there felt bad about my contract being cancelled and gave me an American Express gift card that almost covered the cost. It is one of my most prized material possessions and it is perfect for southern winters. It was a whopping $189 and worth every cent to me.
On a cost per wearing it is even cheaper than many of my other things since I have worn it for 5 years.
I’ve got a pair of $800 Gucci shoes and an $800 Jean Paul Gaultier Jacket.
Hee hee. One of my close friends (girl) has a pair of these. My Docs (sort of a brown/cordovan low boot with padded edge at the top) were $135 so I guess that’s the most expensive thing. My Danskos and Birks at $100-110 each come in second. It’s all about the supportive shoes.
My prom dress. $300, a plain red A-line, and yes I actually have worn it again since I graduated (For the university ball last year). Though one of my jackets comes close in price, I barely wear it anymore, having bought a new fall/winter jacket a couple months ago.
Got a handful of things in the $400 range - custom-made boots, and some motorcycle leather - jacket, pants, etc.
My boots for Ren Faire are also in that $400 range
Most expensive single item I have is some leather overalls, at about $600.
Cows ain’t cheap!
I have a couple of $800+ Brooks Brothers suits.
The most valuable piece of clothing I own is a cashmere sportcoat, originally price at something like $1.800. My girlfriend bought it on sale at something like $300, though. It is an absolutely luxurious garment.
$600 suit, purchased just recently. Looks sharp.
After that, prices drop off dramatically; for a long time my upper-body wardrobe was entirely free T-shirts from the tech industry.
I spent about half of my Christmas bonus on a $240 LL Bean parka. I guess I inherited my parents’ shopping sense, they grew up duing the Depression and raised ten kids.