May I ask which size handbag you have, and if it holds an iPad? That's a very impressive, tempting site! It is, isn't it? :) I have the Retro Cross Body Handbag style:http://oberondesign.com/oberon-accessories/handbags.htmlI think the bags run slightly smaller in person that what they look like from photos, or even gauging from the dimensions given. When I look at mine in person, it looks shorter, and slightly wider once it's filled, than the look you get from one of the larger screen-shots of it. The Cross Body is good if you're looking for a modestly-sized bag. Each side is just a little smaller than a sheet of paper. Bigger than a clutch, smaller than a tote. It's big enough to hold a Kindle 3 Keyboard in a cover (either horizontally or vertically), my Panasonic Lumix DMC-ZS5 camera in its carrying case, my little neoprene hand-wallet (about the same size as the Lumix cased, my sunglasses (hard-cased), reading glasses (hard-cased), an IPod Nano (cased), a small set of keys, a small hairbrush & a small bottle of hand lotion. A small makeup bag wouldn't fit when it has the above items in it. If I didn't carry the camera, it would. But a few makeup items can slide individually in the storage slots, if they're not bulky. I carry my cell phone clipped to the outside (or to me), but you could easily slide it in one of the interior pockets. I prefer not to zip a bag open to answer it. The cased Kindle 3 fits perfectly inside the large interior pocket. Not a lot of extra room, but no struggle to get it in either.But since my Kindle's cased, I find it just as easy to slide it in alongside the wallet/camera/glasses. All those all store vertically. If you carry a clutch-style wallet, the kind that can hold a checkbook and has a little change purse, that fits too, either horizontally or vertically. I experimented with my MILs. I find there's not a lot of play in the interior storage slots, or room to shove a hand, especially once you put your items in the middle of the bag. The bag is structured, so you aren't going to make it squeeze out much wider when you fill it up. And it would look silly if you did, with lumpy sides. Three of the slots are "4-fingers-width", to give you an idea of the size. Two are 3-fingers width. There are also Kindle-width slots with velcro closures on each side of the bag.I find I can put my reading glass case in a 3-finger slot. But I prefer the way they stack vertically in the middle. I use a slot for the IPod Nano. Actually, the bigger one, the logistics just work out better that way. Another holds my little rubber, squeeze-type coin pouch. The other 3 smaller slots hold frequent shopper cards, gift cards, business cards, etc. They're also good for a few smaller or thin items that you can insert vertically - a lip gloss, mascara, comb, etc. My chunky sunglasses case doesn't fit well in the slots - well, it fits, but it just makes the interior bulge awkwardly. It works fine vertically in the larger, open middle area.I think I am going to use the larger slots with velcro for papers and receipts. I can't see them working for bulky objects. A standard envelope for an 8 1/2" x 11" sheet of paper fits well. Size-wise, they're about the size of a half-sheet of paper. If you like putting your receipts in an envelope, they'll work well for that. It's a moderate size if you want to carry "enough" but not the kitchen sink. If your style is to just toss things in a bag, and you have more than a couple of things, you might not like it. If you like structure and putting things in their place, with a more minimalist size, it works great for that. Obviously, if you don't carry a camera and 2 sets of cased glasses, you'll have room for another assortment of items. The bag probably works best if you like to keep your smaller items cased, since it's modest size doesn't let you rummage around easily like a "hobo-style" bag.If you need to carry a few papers from work, it has a little room but not a lot. I have several sheets folded in half from my last job. They fit alongside the Kindle. I don't think I'll use the large storage slots for them. The width of the bag, and the zipper opening, make that very awkward to access with a handful of papers.The shoulder strap lets the bag fall between your hip and upper thigh, a comfortable distance. It has 1 hole shorter and 2 longer from there. At the longest, it works for cross-body, keeping that same hip/thigh distance. I decided to go with that style, so I could use it in Europe as a cross-body, if I wanted to when traveling. The Streamlined and the Tote have the double-handles. Speaking of travel, the larger pockets with velcro work for holding a passport or boarding pass. You can fit the passport in one of the 4-finger slots too, but it sticks up a bit, as they don't go as deeply down the bag as the larger pockets. Maybe easier to access, but more visible too. I can see the top of the passport in the larger pocket & pull it out, but it's more discreetly out-of-sight, which is not necessarily a bad thing.If you travel with a magazine, you are not going to be able to fold it in half & stuff it in this bag. AFA comparing the size to some of their other bags, I'd say the Streamlined is going to be a bit bigger than the Retro. But not scads bigger. The height is virtually the same (8.5" vs 9"), but it's wider (14" vs 10"top/11.5"bottom for Retro). Just a hair deeper (3.75" vs 3.5"). I suspect it might give that little extra rummage room that the Retro doesn't have. It also looks a little less structured. The Retro stands upright on its own very easily, because of the way the side-panel is structured & stitched in, giving it its width. The Streamlined is sewn onto itself, which seems like it would be softer or slouchier. But it won't be a "slouch" bag per se, as the leather is fairly firm, if that makes sense. AFA your IPad, the standard IPad is 2" taller and 2.5" wider than the Kindle Keyboard (assuming you don't have the mini). The width is no problem in the horizontal position. But, hmmm....I think the height might make for a tight fit, working it past the zipper. When my cased Kindle's in the bag, I have about 3-fingers width of space extra. That's just over 2". It's "ok" maneuvering the Kindle into it horizontally past the zipper and into the bag (even easier vertically), but that extra 2" of the IPad would make for a very fiddly, tight squeeze at the best, I think. If I have those dimensions right, it would fit in the Streamlined (or Tote) much better. MIL has had an eye on the bag, since I experimented with her wallet <lol>. She thinks its stunning. It might end up being her birthday present, since that's coming up next month :). I know she likes to carry just a few items in her purse, especially when she goes to Portugal. So the size would work for her. And she loves the ornate design. HTH,Laura
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