Connie Wang, global editor — H&M
"I always underestimate H&M's seasonal sales, and find myself, mouth-agape, in the aisles just flabbergasted at how cheap the items that I've been wanting to buy all season actually are. Take for instance, these printed trousers — I've been making a point of stopping by H&M since spring to pick up a few pairs. And now that they're all under $20, I went absolutely bonkers (additional brocade, floral, and checked pairs, not shown). The mohair sweater gave this look a slightly '50s feel and is made with the fuzziest, softest yarn. Additional surprise discounts were taken off at the register, and I was left with a $18 surplus that I could have used to "splurge" on a necklace or a clutch...or — let's be real — another pair of pants."
"Though this dress and jacket are definitely from H&M's spring collection, there's something really subversive-feeling about wearing pastels during the winter. I'd wear these with glittery tights and boots to my holiday parties paired with obnoxious rhinestone jewels. And fine — I went over $3, but these clip-on rose earrings were too cool not to get."
Gina Marinelli, assistant editor — Target
"My strategy was to find the most impactful pieces for as little as possible...so I headed for the sales rack. I was first drawn to the color of the pants (oxblood, wine, whatever you prefer to call it) and then the graphic sweater. I piled them on with a sheer shirt that added an extra layer of texture, and still kept it all well under budget."
"I could not believe I found this skirt at Target (and neither could a few other folks in the office). From the moment I spotted this neon-striped number, I had to build my whole outfit around it. A simple sheer top — stolen from my first look! — and a sparkly clutch is all I needed to be completely holiday-party ready."
"I'm a huge Uniqlo fan, so this Cheap Challenge was a particularly fun one for me. Well seasoned at navigating its imposing stores, I went right for the special-promotion tables, which, especially in the winter, always offer up awesome deals on super-nice sweaters. I also found these pants, which are my new favorites and are giving my Uniqlo jeans much-needed time off. They are as comfortable as sweatpants (helloooo, stretch-waist band) but they look good enough for work with a subtle sheen (and they come in a variety of patterns). As soon as I saw them, I knew I would build my look around them. They are a good basic but are far from boring. To me, this is the ultimate weekday ensemble and would work well for a woman of any age. "
Willow Lindley, fashion and beauty assistant — Uniqlo
"Uniqlo is all about basics, but that doesn't mean that it just offers jeans and tees. Again, I searched for special deals on things that were patterned, and found this cozy and cute dress that is ideal for winter weekends. It was a little more expensive than the pants, but going for a dress in a Cheap Challenge is always a good idea because it doesn't take much to turn it into a full look. This chic top hat was the perfect accessory (Uniqlo doesn't have jewelry or many other accessories, but their winter odds and ends are great). I think it keeps it from looking like a nightgown you'd wear in a cabin in the woods."
Photographed by Erin Yamagata