My search began at Urban Outfitters, where pushy shoppers and loud techno music almost ran me out the door. But after a few deep breaths and some digging, I grabbed a red bell-sleeved knit dress from Lux. It also comes in taupe (drab) and black (boring). The V-neck cut was very flattering, but the material felt cheap and the skirt was too long. Though inexpensive ($78), the poor quality made it worth even less. 526 Sixth Ave., at 14th St.; 646-638-1646.
Heading uptown, I stopped into French Connection and was immediately taken with a light-gray knit mini, priced at a reasonable $118. With a tie belt and a deep V-neck, this understated dress was unquestionably sexy. But although I liked the feel of the soft wool, the cut was too clingy, especially in combination with such a short. It could look good with tights, but it was just too revealing, especially for winter. 1270 Sixth Ave., nr 50th St.; 212-262-6623.
Heading home to Williamsburg, I hopped onto the L train, which was jam-packed with girls actually wearing sweaterdresses. At the consistently stylish Otte, the racks were filled with soft knit sweaters and tunics. A gray, short-sleeved dress ($272) was disappointing at first glance: The bubble hem and mock turtleneck made me cringe. But once on, the full skirt draped beautifully and the shape created a slimming silhouette. If I could afford it, I’d happily wear this dress all season long. 218 Bedford Ave., nr. N. 5th St., Williamsburg, Brooklyn; 718-302-3007.
Red Pearl, Williamsburg’s home for hippies, was overflowing with sweaterdresses, most of which were itchy and uncomfortable. I tried on a long-sleeved, pleated miniskirt version. Although the colorful details on the cuffs and at the neckline were pretty, the dress reminded me too much of a Catholic schoolgirl’s uniform. At $285, however, they just weren’t pretty enough. 202 Bedford Ave., nr. N. 6th St., Williamsburg, Brooklyn; 718-599-0023.
The next day I braved the rain and headed to Anthropologie. I picked the wrong day to go: The store was crowded, and the normally plentiful boho knits were reduced to a pitifully small selection. I did find a Tracy Reese number ($288), which came in black or white and hung perfectly. The somewhat see-through dress was unbelievably comfortable. I would have bought this dress, but they were out of extra-smalls (it runs big, so go down a size). 85 Fifth Ave., at 16th St.; 212-627-5885.
Wet and a bit bedraggled, I headed over to Intermix to check out some high-end options. I immediately fell in love with the M Missoni Zigzag Dream dress—a knee-length stretchy wool knit patterned in classic Missoni stripes. The extra stretch made the dress very comfortable, but it was too clingy on me. If you can afford it, this pricey style ($565) would make a great winter party dress. 901 Broadway, at 20th St.; 212-533-9720.
At the tiny Basic Basic in Soho, I found a very cute Rebecca Beeson hooded sweaterdress ($187). The banded waist on soft wool gave the shape more definition than many of the tunic-style dresses. However, as pretty as this dress was, the combination of the flippy little miniskirt and hooded top made it too childish. Unless you’re going for a preteen look, I’d skip this one. 710 Broadway, nr. 4th St.; 212-477-5711.
The last stop on my quest was H&M, where I was determined to find a bargain. Scoring a good deal was no problem, but finding the right size was. I discovered a cap-sleeved green sweaterdress in a slightly see-through, itchy wool that was a perfect fit. The highlight is the baby-doll shape and tie, which creates a super-flattering empire waist. Though you might need to get something to wear under this dress, at $34.99 you really can’t go wrong—which is what I told myself as I waited in the long register line. 640 Fifth Ave., at 51st St.; 212-489-0390.