I'm kind of busy with work, trying to finish everything coz I plan not to come in my office from this weekend until the first week of January. I'm not taking leave, but I'll be traveling every weekends starting last weekend. The rest of the time will be in the field and other sites. Not to mention all the visiting with suppliers and clients to give them gift basket and say thank you for the last year and the next. It's a tradition here.
Unfortunately, my hiking trip last weekend was good except that I sprained my ankle falling down a steep hill on the last day. Luckily it's not a bad one. The doctor already did the x-Ray and nothing is broken. I'm so glad coz I have an amusement park trip this coming weekend and I don't want to miss it. Walking will be a lot slower during the week, but I'll be fine.
Regarding the questions,
The bag I often use when I want to feel elegant is hands down my Chanel jumbos. There's a very strong vibe coming out of them that gives me the feeling. I just feel instantly dressy whenever I wear them. And this apply only to the jumbo. The other size and style although give the same vibe, they're not as strong and always have other feelings mix in.
I think my best purchase is the Bally Widehorn. I hope you all won't get bored with how much I keep talking about it, but I just love it! It's the style I've been wanting for a long time, in the new material I never have, and in the color that I want. The size is good and the strap is adjustable. And I got it with great discount! Although, there's a bit of the trauma when I first got it, I think it's a really good buy for me.
I agree with you about the smaller bags are not cheap. There's quite a sticker shock for me, too, when I learn how much they cost. I only downsize stuff I'm carrying coz my shoulders hurt to the level I don't want them to anymore. Still, I need my planner and other stuff with me and still, I wish I could carry a book with me all the time.

As much as I like browsing app on my mobile, I'd prefer to finish another chapter of my book-at-the-moment. With this, I think I'll need to break out another bag that's still small, but can offer more space. I'm thinking of using my more delicate bags, but I'll see when I'm home this weekend before the trip.