Mastering Indian-Summer-Wear

I'm trying to enjoy every last drop of this week of Indian Summer here in Chicago. News reports are already torturing us with the "warning" that ours will be the worst winter in the country this year... Jerks. I don't know how to prepare mentally for that. I almost wish it could have been a surprise. Instead, I'm already starting to panic about my likely turn as a recluse in the months ahead. Not good. But NOW. NOW it's warm and delightful. That magical bit of warmth and sunshine that taunts you with the memory of summer neatly set in between cold spells. I'll take it. If this is the winter I throw up my hands and give up, then I'll suck the life out of these last yummy-warm-happy days.

But I feel weird dressing summery when it's October, you know? Like, it's warm, but it's just warm-er. It's not summer again. It's fall. Just a bit of meteorological comic relief to help us out, but still fall. I think I got it right (or at least acceptable) from head-to-ankle, but I think I went too summery with the footwear, and I knew it when I put them on, but I didn't really have the *right* fall/Indian Summer shoe, so I just went with it.

(Please forgive: a) my beautiful background of my office; and b) my aging rock star (aka Richie Sambora) hair... that's another story for another day...)

(Also, I mentioned the bracelet before here, and the shirt here)

But see what I mean? Too summery with the sandals. Maybe something like this would be more Indian-Summer-appropriate:

(DSW)

(DSW)

(ModCloth)

Or even something like one of these:

(Urban Outfitters)

(Endless)

What do you think? Which would have worked better for between seasons? How do you dress to fit these not-quite-a-season days?