Yeah, that fake tree was a blow. But it was so freaking easy! Pre-lit!
Gardening clogs. For that matter, a whole crapload of gardening stuff. Including an elaborate seed germination station.
A fur coat, a motorcycle, and Santa/Mrs clothing.
For me, it would be an MP3 player. I decided to go with the technological flow and I’m glad I did.
A curling iron.
Born with riotously curly hair, why would I need a CURLing iron?
I have a ceramic flatiron to straighten my hair and sometimes the ends just look nicer when slightly curved under…Yes, I artifically iron my hair, naturally curly, straight, then artifically curl my artifically straightened hair.
I never thought it could happen to me.
A sequin dress.
A heating pad.
A handgun.
A cigar lighter that cost more than $100. I remember seeing them when I was younger thinking that was crazy. Then my wife got me a $100 Colibri for Christmas, and now I wish I would’ve had it much sooner.
Getting ready to be an Ipod Video.
A pickup truck.
If my 18 year old punk rocker self could see his 38 year old self, he would be terrorized.
You tie. I own one as well. Had mine since '82 IIRC.
How did you two end up with stuffed armadillos? Were you driving down the road, hit one, and decide that it would look nice above your fireplace or what? 
A friend’s mom had a booth at a flea market. The next booth over sold stuffed armadillos (and other stuff). Paid $45 I think it was…
Running tights.
First, the notion that I would run without being chased by something has, until approximately one year ago, been completely ludicrous. Add the image of me, in skintight Lycra, along a public right-of-way. Then consider how much I, a notorious skinflint, paid for said garment.
It’s utterly preposterous, I tell you.
Bottled water, like Dasani or Aqua Pura. I once stated that I would never buy water when I could get it for free at the spring. Now that we know what’s in the spring…
I can remember about 11 years ago, thinking, 'Hmmm…all my music is on cassette and vinyl. I’m not sure I would ever use a CD player." I bought it anyway. Now none of my music is on cassette and vinyl and ALL of my music is on CD.
Bottled water, mineral water, sparkling water, a computer, DSL, and a cell phone.
After getting stuck in a snowstorm and not being able to reach my daughter, who was waiting for me to pick her up from volleyball practice for an hour and a half, I finally caved and bought a cell phone. For her. Just a few months ago I swore I’d never buy my children cell phones because they were just status symbols.
That sounds like a party no matter how you look at it.
For me: I never, ever, ever thought I would own a life insurance policy.
A speedo (I’ve since worn out three of them)
marathon registration
and the most unlikely: an engagement ring (6 weeks ago)
An answering machine. My mother and grandmother constantly complained about how rude it was to have an answering machine answer when you weren’t home, so I avoided them like the plague. Then I got one for Mr. Kiminy as a wedding present. It turned out to be one of the best investments we ever made, and I can’t imagine not having one anymore.
A cordless phone. Why on earth would anyone need to walk all over the house with a phone in their ear? We found out after our first child learned to crawl, then walk.
A cell phone. I finally broke down and got one for myself after spending several hours trying to find a pay phone to make sure that my daughter was okay after getting home by herself. I was also in my second job where there was no easy way to reach me using the company telephone. (The company didn’t mind emergency calls from school, of course, but it was hard to track me down when they did come through.) Mine turned out to be so useful that Mr. Kiminy finally asked when he could have one, too.
A hands-free headset for the cell phone. I don’t think that it is really any safer to drive with the hands-free than without it, so I just don’t use my phone when I’m driving at all. However, the headset is VERY nice when you are on hold for eons, and it works with the cordless land phone too. 
Two things Wimmen Dopers will unnerstand:
Fat girl undies. Y’know, Thar She Blows panties. From Thongs to Grannie Panties in the Blink of an Eye…
Three hook bra. I will never go to a four hooker.
:dubious: In my experience, colibris tend to keel over if they get too close to a cigar.