Insomnia Shopping: Or How I End Up With Things I Don't Really Want (And Some I Do)

My sleep's loss is my closet's gain.

I've written here before about my slightly disturbing nocturnal activities, like organizing my feelings via my closet and the Container Store. But now that my wardrobe is categorized by the Dewey Decimal system, what's an occasional insomniac to do next?

Find more things to put in my closet and organize, of course. When you're awake and alone at 4:06 in the morning, sometimes you imagine--and panic--that there are gaping holes in your wardrobe that you simply can't go another day without. And, yes, sometimes Ambien has something to do with that.

Which is why I set out on a shopping odyssey recently, through time and space and my laptop, to buy things that I couldn't believe I didn't already have, like a painting of a fierce tiger, a white v-neck t-shirt and an alligator purse.

Here's a little rundown of what was inside the boxes that appeared at my door days later:

What: Fierce Tiger painting, $25,

Why: What's not to love? It was probably done by an amateur artist in upstate New York and I love the awkwardly unfinished paws. It hangs near my closet and inspires me to no end.

Level of regret: What's to regret?


What: Givenchy chain necklace, $49, (other ones sort of like it here)

Why: I can't quite remember. I threw in some cheap gold non-Givenchy chain bracelets, too.

Level of regret: The jury's still out. I get a lot of use out of the bracelets all stacked up with a watch and other gold wristwear, but I haven't worn the Givenchy necklace yet.


What: Vintage cotton v-neck tee, $29.50,

Why: Can you believe I didn't have one of these guys? Neither could I. What an important basic--either for pairing with jeans or dressing up with a skirt and a statement necklace. So I bought two because they--gag--get yellow in the armpits real fast.

Level of regret: None whatsoever.


What: The Bob Dylan "No Direction Home" Soundtrack CD, with a $50 contribution,

Why: If an NPR pledge drive overlaps with my insomnia, NPR gets my money, end of story. And as part of my $50 contribution this last round, I accepted one of the gifts that you're given the option of not accepting if you want all the money to go to NPR. I already have a whole mess of tote bags, so I went with this CD.

Level of regret: High. I love Bob Dylan, but I hate dealing with CDs, and I will probably never, ever open this one. I should have let NPR keep those 16 bucks.


What: L.L. Bean Boat Bag, $15.99, (but also available at

Why: But obviously I do not own enough tote bags. I'm experiencing some serious New England style nostalgia lately, so I had to buy one of the bags that my high school teachers always carried papers in for grading. Now I bring this one to the gym.

Level of regret: Moderate. Seriously, I do not need another tote bag.


What: Vintage alligator purse, $60, (you can get similar ones here)

Why: So before I start looking like a total Brooklyn liberal cliché, I thought I'd show you something truly repugnant. This bag was made in Cuba from a baby alligator and was all the rage in the 1940s. I couldn't resist.

Level of regret: Meh. I mean, that alligator must have been so cute, and it is kind of weird to walk around with taxidermy hanging off my shoulder. Plus it needs some repairs because the skin is peeling off all over the place. But isn't it unique? And it was secondhand, which is the only way I'll buy dead animals.


What: A caftan, $15, (similar ones here)

Why: God, I love a caftan. I love the '70s and I love dressing like I'm on quaaludes, hosting a suburban swingers party or drinking mai tais in the afternoon.

Level of regret: Zilch. I wear it both in the house and out, with a belt and blazer.


What: Coach purse, $29.99, (similar ones here on eBay or from the new, pricier Coach Classics line)

Why: Coach makes the best no-nonsense leather purses, with no obnoxious logos to be found.

Level of regret: None. Like the white v-neck t-shirt, I couldn't believe I didn't already have something this basic in my possession. I just need to go to the cobbler to punch a few extra holes in the strap since I'm quite the shorty.


What: Jersey Lomellina cinched bandeau, $58, and bikini bottom in Earth, $56,

Why: I was about to go on vacation and I was desperate for a bikini that didn't cost $300.

Level of regret: Low to moderate. The butt is a little saggy, and if I hadn't ordered a bikini online (the only way J. Crew sells swimwear now) I would have foreseen that. I've since found a better-fitting bikini at American Apparel. It's important to love thy bathing suit. I wear them at least once a week in the summer.


I also bought a bunch of other stuff on, which I just returned at a store. Of course, I then walked out with more new stuff that I will probably return later, and so the cycle goes.

So do you insomnia shop? What late night purchase do you most regret?