Canvas has an even more limited lifespan and you might not be able to wear in the rain or snow. Leather is much easier to clean and waterproof. Plus, you will need to walk the Earth and back to wear off that rubber sole IMO. A high top leather sneaker has a much different feel than a canvas one. The outfit in your inspiration photo is elevated exponentially because of them.

I had intended a response to Parsley: you think it's a Hermes bag? I'd assumed it was street...that would require a substitution.

I don't usually go for orange, but it looks so punchy and bright. I am not sure, but I think orange and blue are at opposite ends of the color wheel, right? I somehow think it would not be the same with another color. mDitto for the cons. They're sort of receding, but present with this unassuming coolness.

Of course, I could just be babbling nonsensically.

Good points, zap.

No -this is NOT nonsense, Mochi. This is part of why the look works. Orange and blue ARE opposites. But instead of a bright blue or orange, you've got a navy (greyed/ blackened) blue and a burnt orange for most of the accessories.

I will ditto what Zap says about leather sneakers. I wear Ecco walking shoes for all my athletic stuff. They are supposed to be walking shoes, but I wear them for running, cross fit, weights, everything. And here's the thing...I ALSO wear them when I'm travelling. And in the rain. They are indestructible. I wore one pair every day for almost three years and the tops were still in great shape.http://biom.ecco.com/en-XI/BIOM-TRAIN

Okay, so they are not as cool as Cons. But you get the idea. Leather makes sense, even though it is pricier up front.

Have not read the entire thread, but I love this look for you! I can see the thread of continuity between this and the Italian outfits of previous links in the playful combinations.

I'm pretty sure it's a Hermès Jypsière bag.

http://www.lyst.com/bags/herme.....4-leather/

I think this look is based on well-fitting classics - skinnies, striped top, blazer. All the fun is in the detail.

Wow, it really is a gorgeous bag. But I'll bet there are some nice knock-offs.

great outfit to aspire to. DO you have the jeans, the striped shirt and blazer already? the accent of orange is the accent and that you can switch out with angie recommended accessory groups. Here they used orange/camel colors in shoes, bag and scarf, but you could do red, or whites, or whatever, once you have the basic outfit in the box!

I look at this photo and I think, "Of course! Why wouldn't this be EVERYBODY'S aspirational look?" LOL LOVE LOVE LOVE

Inspired by this post and Angie's high tops blog post, plus the fact I kept putting on my beloved greige summer cons but realizing they were too light coloured for fall, I ordered high-top dark grey converse and swapped the white lace for a grey one that doesn't quite match (effect is tone-on-tone I guess).
I'm happy with the results and wearing them with skinnies today, but I did realize it's not just the white lace but the big white toe/slim ankle combo that's a little clownish to my eye. The laces are a little short so I stopped one short of the top and the ankle isn't quite as slim that way which helps. But I like the tweedy converse posted above, plus a wider ankle, so I still have my eye on that look. Aldo has some versions too (I like paveya and carrejo, see second page):
http://www.aldoshoes.com/ca-en.....s/sneakers