Smartwool socks ($15+): These are the most comfortable pair of socks you will ever own. When I bought my first pair, the sales person told me about a friend of hers that went months without washing his and they still didn't smell. While I don't recommend subjecting them to that sort of abuse, they can handle all sorts of harsh indoor and outdoor activities while keeping your feet feeling toasty, pampered and importantly, non-itchy.
Furni's Alba clock ($88): so cool even design-unconscious people will appreciate the aesthetic value side. Plus, according to my hubby, one can never have enough alarm clocks.
Black Diamond Headlamp ($35): even if your special someone thinks outdoor activities (especially those in winter) are for the uncivilized, masochistic or mentally unstable, they'll appreciate one of these babies for those late nights they need to find the keys they dropped or that pile of dog poop their (normally obedient) pupper placed on the neighbour's front lawn. Sigg Water Bottle ($20): apparently my beloved Nalgenes are killing me with every sip. These sexy things keep your water carcinogen free and tasting fresh all day.
Purdy's chocolates ($23 for 1 pound): I don't even like chocolate and I eat these. The coffee creams alone are worth killing your grandmother for.
Envirosax ($40 for 5/$8 each): a reuseable shopping bag that allows you to coordinate your outfits while saving the planet. Save someone else from being tempted to use those damn ugly 99cent President's Choice bags as purses.
Stovetop Bialetti espresso maker (~$20): this sturdy little sucker can be used on any type of stove to make tasty expresso-based beverages on-the-cheap. Best unadvertised feature: can be (carefully) used on the BBQ when the power goes out.
Pac Man hot water bottle cover ($15): Gen-X nostalgia and winter comfort - what more could you ask? Yes, even boys get cold toes sometimes.
Chunky handmade mug: even people who don't like hot bevies would find this a handy beer stein. If they don't like beer or hot drinks, they're probably not someone you should be wasting money on.
Screen printed band posters ($20): give the gift of instant street cred by buying ones for obscure, up-and-coming bands your friend has never actually seen or heard. FYI: the Weakerthans are not new but merely Canadian and, as such, naturally underrated but loaded with cred.
Ikea's knock-off Le Creuset cast iron pot ($70): so you can help someone else discover the miracle of no-knead bread.
Tasty Kicking Horse coffee ($40): help to convince another coffee lover that Starbucks is only good as a place to take an emergency potty break.
The Riddick Trilogy ($22): At the risk of overgeneralizing just a tad - men want to be him, women want him to impregnate them.