I carry a macbook air around daily, which is slightly bigger. I like hobos or totes. I have a Mulberry Alexa which is crossbody but I find it's harder to control and I don't want my stuff to get jostled. Totes (or even large shoulder bags) with big straps or hobos can stay tucked under my arm and out of harms' way.
To be honest, all my bags are too slouchy with no compartment for an iPad. So I just use a separate sleeve for the iPad and then throw that into my bags. It works well enough, and that way I don't have to have my iPad dictating which bags I buy!
I put the full sized iPad in my Bottega Veneta Roma tote when I take it out on business, and it also fits into a Burberry bag I have (Small Hepburn) It will also fit in my new Alexander McQueen bag (the Heroine). I use a soft case for the iPad. It fits in most of the Tod's totes too, don't own one yet but tried it out in the store recently and it works great in the medium sized bags (not the Picolos). I would not carry one crossbody, too clunky, and too tempting for someone to make a quick grab for it, in NY City, anyway.
there were times when I carry my iPad daily, I used to carry it inside my Balenciaga city/part time, or Chanel gst
I prefer a shoulder bag to carry iPad or MacBook Air, I always feel a sling bag weigh down weight stuff more than a shoulder bag do
i use a small beige givenchy antigona to carry my ipad to work daily.
it fits my iphone, my makeup pouch, kindle (4th gen), wallet, cardigan/shawl, a small bottle, card holders, battery pack for my iphone and my headphones. there's still space for more, but because the bag is rather heavy itself, i don't usually carry more. i don't drive, so carrying anything more would klll my back!
i don't use my ipad with a sleeve. when i do, it's only because my tiny bags can't fit the ipad
iPad mini is a great solution to this issue! Though it doesn't have retina display and isn't as fast as the iPad 4, it's worth it due to the smaller, more manageable size and weight IMHO :)
That said when I carry my iPad I just use a longchamp small size and it fits fine
this topic is my life. i'm always looking for a bag that can fashionably hold my laptop and other daily necessities. totes and hobos are the best shapes. right now i'm using a Zara bag (the Office City Bag, purchased in Sept). It's similar to the Prada Saffiano Lux double zip bag. It's huge and has a strap. It has a padded middle zip compartment for a laptop and another padded compartment for an iPad. I don't have an iPad, so it's just an extra pocket for me