In no particular order, last checked May 4, 2014...
The local gay/lesbian/bisexual/transgendered group, the Pride Centre of Edmonton, has an excellent site. I cannot recommend Edmonton's branch of Illusions, as the current president is a convicted pedophile who is doing as little outreach and Winterfest activity as possible, and is attempting to bully others into his personal beliefs. However, the Calgary branch has few such issues. Political interests can be followed at the Trans Equality Society of Alberta. The Imperial Sovereign Court of the Wild Rose is Edmonton's link to the local drag community. OUTreach Edmonton at the U of A meets monthly, are sincere about what they're doing, and have a progressive website. The Jasper Pride group deals with the central Rockies, and the Bow Valley Community serves the Banff and Canmore region of Alberta. Winnipeg's Masquerade socializes the second Friday of every month and really have their act together. Regina's got it together with their Gay&Lesbian Community Club. The girls in Vancouver's Cornbury Society also have a good-looking, very informative website.
In the East, Toronto's Xpressions group is strong, active, has a very spiffy site, and are associated with Ontario's Spring Fling and Fabulous At The Falls. Egale Canada, also based out of Toronto, has lots of resources for all members of the alphabet-soup communities. Ottawa's Gender Mosaic has been happening for as long as any other Canadian T group. Montreal has support org ASTT(e)Q, and the activist group Centre for Gender Advocacy.
I was one of two club members featured in SEE Magazine's 2002 article on local crossdressers; the interview was interesting, and the photo shoot was a blast. A more recent Sun article in 2016 showed my image as a lead photo; this is the Real Me, folks! Mike Ross at Gig City had some fun with this writeup on the 2017 Big Valley Jamboree parade.
As well, I use the word "tranny" to describe what I'm doing, and don't find it offensive. Justin Bond made some pithy comments on the subject; I couldn't agree more. Julia Serano has written an interesting essay and glossary on the terminology. Riki Wilchins, in the Advocate, also refers to the term as important. And Joshua Ferguson makes several good points about non-binary transpeople in this Huffington Post article (though I don't agree with all his opinions on pronouns).
Sister Mercy, also known locally as Mercedes Allen, has put together an Alberta Trans website, and has recently rewritten an excellent History of Transgenderism. I've found the Digital Transgender Archive to be just as informative, as well.
Renee Reyes is an Atlanta gal who has been there and done that, lives her life to the max, and shares a great mountain of good tips. Kathryn du Bois offers good reading on being a fashionable crossdresser. Susan's Place Transgender Resources is a TG support resource which provides information of use to transsexuals, crossdressers, and their families. It's neither mainstream nor all-encompassing, but there's Good Stuff here. Rachel's Place is a fine site full of tips, photos, and commentary valuable to crossdressers, as is Lucille Sorella's blog. Another resouce, comprising radio podcasts, video, and print media, can be found at GenderTalk. Aussie tranny Emily Farnon also has a cheery and interesting website up for helping newbies. Stana's Femulate is an intelligent blog that's worth following too. Sister House is yet another interesting group where trannies hang out to share and converse. Crossdresser Heaven is, on the surface, a good place to meet and share with other trannies, but upon close inspection, tends to reinforce a lot of the fear and tentativity endemic to this special interest. Look it over and make your own decision...
Kalina Isato's Transvamp.com is an easy-reading trove of the Good Stuff from one of Philadelphia's finest TG gals. Good humour, tips, fine photography, and opportunity to buy product abound here!
Femme Fever is a gentle and positive transformation service on the Eastern Seaboard; the site is low-key but complete, and quite inspiring.
Tri-ess is a support group for heterosexual crossdressers and their significant others. There's sensitivity and intelligence at this site, and contacts for the American chapters (not much happening up north here with them, other than a monster convention in Kananaskis in the mid-90s).
The World Transgender Association is a trendy, newer group with some good tips and commentary. They even offer official ID, which is a bit silly as it's not accepted by any governmental organizations - but hey, whatever floats your boat!
Check out Asia Carrera's makeup page!
Frock Magazine is the heiress-apparent to past glossy TG magazines as Ladylike and Girl Talk, is free online, and is quite well-done. As well, Brit trannies have TransLiving that achieves the same production values. My biggest issue with these publications is that they tend to apologize to the world for what we do, and perpetuate the hiding that makes transfolk so reviled by the uninformed public.
The Breastform Store has good prices, product, and service, as well as a Canadian site. Those of us who use balloons and rice packs would be surprised at how nice these bits are. Recommended; the self-adhering Amolux Diamond forms are the best of all - pricey but worth every cent. As well, DressTech produces excellent hip forms that will make you toss out your padded panties.
I get my hair trimmed and styled at Est-elle Academy of Hair Design, and can't fault their students' work - indeed, I've gotten several awesome cuts there. Esther, the owner, has hosted makeup and hair sessions for Illusions gals in the past, and the girls are all open-minded, stylish, and competent.
Edmonton's Wig Boutique has been giving local crossdressers excellent service and product for over a decade, and Always Hair For You in Blackfalds has amazing stock and good pricing too.
The Nu2You Fashion Boutique has excellent selection and staff! Higher-end fashion and worth the money. My go-to shop when in the city, it's handily located north of University Ave on 103rd Street (aka Gateway Boulevard), just behind the Timmie's. Just north, on 80th ave, is Plato's Closet, a nicely-stocked, inexpensive secondhand shopper's paradise.
Caprice Consignment Wear, in Edmonton's West End, always treats CDs with respect, good cheer, and fabulous bits for good prices. Highly recommended, as is the ever-so-charmingly retro Redemption Boutique, Sanctuary (for quality corsets and goth/punk apparel), Leduc's Ms. Frugle and Second Glance Clothing, and the ineffable Nightshade Corsets.
Sizing charts are always good to have handy; Groupon has some too. These are North American sizes, though!
Elli Hunter is an accomplished Deutschlander CD whose site is utterly stunning.
There's a list of terminology at ItsPronouncedMetrosexual that comes close to defining a lot of words used in this special-interest group. Probably a good idea to look them over before trolling the Wicked Weird Web! Above&Beyond, while very commercial, provides a lot of products and reading useful to any variety of transgendered individual. The same goes for Suddenly Fem, and Cross-Dress.com, online retailers catering to those who won't shop in the real world. To add a little spice to your dressing, Pierre Silber is a brilliant source for shoes and slutwear. There's a huge inventory at Glamor Boutique and The Fantasy Girl also have competitive pricing with an online presence. You'll find a lot of different product at Nuremberg's Absolutely Special Trade, though shipping costs would rise a bit, and currency exchange can be an eye-opener. Wigtopia blogs a bit on the topic of transgender clients. Proactive Prosthetics in England will make you very-high-end breastforms, but they're not cheap. Be wary of their recommendations for stealth, however. Wear nice boobs and let them clear your way... Also at the high end, Babooms handmakes huge costume forms for almost $2000, along with products from the RealDoll folks at Real Gurl.
Wikipedia has a very good and fair description of crossdressing here.
Lilian's site has a large international batch of TG photos and links, from the ladylike to the slutty... and, the Crossdressing Picture Gallery is full of nice-looking TG folks, though there's a lot of dead links here.
Rose's Turn has lots of really nice things to wear. And other things. Oh, my...
An excellent, scholarly site, contrasting feminine and masculine body traits, can be found at Feminine Beauty.
Ilana Yahava's Sand Fantasy website has nothing to do with crossdressing and everything to do with beauty.
I'm a member of the Voluntary Human Extinction Movement - their philosophy is advanced with intelligence and wit here.
And, along with half the online world, I'm a Facebook user, and have a photopage up on Flickr. Our Bandcamp page for Unpopular Mechanics is growing, and there's another live mix on YouTube - starts at 19:18. Here's our Press Kit!