Hayden's Sonia vs. Olivia Harris: Pick a tote for my new vp job

The first two pics are the Hayden Harnett Sonia tote (though I would buy the black).
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The next three are the Olivia Harris large turnlock tote. (Read more about the new Oliva Harris line at the friendly Shoptwigs).

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  1. Which do you think will hold up better in a Chicago winter? (I need to carry lots of stuff usually and I need this to last.)
  2. Is one more classic (and less faddish) than the other? (Both have turnlocks, but the HH Sonia's is tiny, which kind of minimizes the trendiness of it. How long do you think turnlocks will be in style.....?)
  3. Which do you like better overall? (I wear a lot of black. And I believe both are acceptable for my new workplace.)
Thanks much for your help.

P.S. The Olivia Harris also comes in ALL black, making my decision even harder.
 
Nice choices! I'm assuming both are high-quality leather so I think they'd both hold up to the weather. IMO the turnlock isn't necessarily a fad, but it's something I'd consider as far as ease of use (eg, having to clasp/unclasp it every time you close/open). I like the dual strap of the Olivia Harris but the style of the bag overall looks more like luggage whereas the HH looks more like a purse (that may not concern you?) I guess overall I like the HH.

Congrats on the new job BTW!!
 
That's so funny, I was just at Luna Boston yesterday trying on both of these bags!

I wouldn't be concerned about the leather on either (especially in black) surviving the elements.

I don't think turnlocks are at all trendy. IMO the OH tote is more classic looking.

I was undecided about whether the OH is too large, although the softness of the leather on makes it slouch nicely and not look too huge. An advantage of the Sonia tote is that it has separate sections for organization. What I like about the OH is the option to wear it as a shoulder bag or cross-body, so I think it would be better if you want to use it as a travel bag.

Although I didn't buy either, I was leaning toward the OH bag when I left the store (which was a surprise, because I went in primarily to look at the Sonia tote). I already have a HH Havana in black with similar details to the Sonia, so that may have contributed to me wanting something different.
 
Congrats on the job! Overall, I would go for the HH Sonia because I like the contrast stictching and the buckles on the bottom. There's something I don't like about the color contrast of the Olivia.