This includes everything I use to take my self portraits, though to be honest, in the winter any time I can get someone else to be my photographer I do. It's no fun to be out in the cold alone!
Canon EOS 60D 18 MP Digital SLR Camera, $800 at Target - The Canon 60D has been my camera for the past year. The pivoting screen makes self portraits a lot easier!
Canon EF 50mm f/1.4 Lens, $359 at Amazon - My main squeeze, this is a relatively inexpensive lens that takes gorgeous photos when wide open. If you are looking for that dramatic blurred background, this is an excellent choice. The 1.8 for $100 isn't bad either, but the plastic construction isn't very durable.
Canon EF-S 10-22mm f/3.5-4.5 Lens, $679 at Amazon - This lens is used mainly for landscape photography, but I've taken some fun outfit photos with it on a few occasions.
Opteka Rc-4 Wireless Remote Control, $7 at Amazon - An essential piece of equipment for anyone taking self portraits. It's dirt cheap at under $7 and works right out of the box. Plus the battery lasts years. The range could be better and it never seems to want to work half as well in the cold, but it's tiny and wireless and the best solution if you are your own photographer.
Roma DSLR Camera Insert Bag Organizer, $60 at ONA - My solution to the chic camera bag problem - on the cheap! This $60 insert allows you to turn any bag into a camera bag. Keep in mind a bag with a boxy shape and a lot of structure will work the best.
London Fog Women's Knightsbridge Tote, $150 at Nordstrom - Lately I've been using this tote, as it has ample room for my camera as well as all my other things.
Manfrotto MK394-PQ Ball Head Tripod, $80 at B&H Photo Video - This is the newer version of the tripod I use, the 725B which was discontinued several years ago. It's light weight, can be set up and broken down in seconds, and once you have a tripod with a ball head, you'll never want any other kind.