So far, I've had reasonably good luck with Old Navy's "The Sweetheart" skinny jeans, KUT from the Kloth brand skinny jeans, and also GAP's "Really Skinny" pants (not jeans, but their 'really skinny' premium pants which come in black and in grey).
I need to go and try on GAP's "Always Skinny" jeans and their "Real Straight" jeans - but so far, I'm impressed with their "Really Skinny" pants - in fact, today was the first day I was able to wear skinny pants tucked into tall boots (yay - I can be a lemming now...lol). In the meantime, the ON "Sweetheart" skinny jeans have worked out reasonably well for wearing with flats, and the KUT from the Kloth jeans have worked very well with sandals, flats and short booties, but I haven't yet tried tucking them into tall boots.
I'm with HelloKitty - I think you might want to try skinny pants or jeggings/leans first, as opposed to actual jeans. The jeans aren't always so easy to tuck into boots, and at this time of year, you want something you can tuck into boots, as far as I'm concerned.
I'm so pleased with my brand-new GAP "Really Skinny" pants - extremely comfortable and a lot easier to deal with than jeans.
Do not despair - there is a pair of skinny jeans/leans (ie. jeggings)/pants out there for you.
I think "leans" (YLF's better term for "jeggings") is a great idea, as per HelloKitty.
Just for the record, I had to size down for GAP 'premium' 1969 jeans, but I actually sized up for the Really Skinny pants.
Try GAP's "Really Skinny" pants next. They look great, and are extremely comfortable.
In terms of skinny jeans - so far, the KUT from the Kloth brand has been the best for me in terms of flattery and fit, without veering into $200+ jeans territory. That said, I don't know if these are available in Canada.
In the meantime, I have also had kind of a tough time finding skinny jeans/leans/pants that I feel comfortable in, and I ended up buying GAP's "Long and Lean" jeans (not skinny at all) and their "Really Skinny" premium pants *instead* of skinny jeans. I got so tired of trying to find skinny jeans that worked, and ended up with the Really Skinny premium pants from GAP instead - very happy with these.
You will find a pair that you feel good in - promise!