Condom Hat

On the LYS tour last year, I got a skein of Sheep Shop Yarn (Sheep 3) that i wanted to knit a hat with (the hat that came with the yarn, actually). It was a speedy little hat, and rather cute as I was knitting. And then I put it on. Now, generally, I don't wear hats. I have a hat I wear in the rain, which has a brim, and I think I look rather cute in, and there's a hat I wear when it's cold to walk the dog (i generally don't care about cuteness then). So knitting what is essentially a beanie, might not have been the greatest idea. It was a little snug. In fact, I started calling it a condom hat. The ends were never woven in. But I had enough yarn left over for another hat, so I copied my friend Genypher, and knit the Clamber (ravelry link) hat. Her hat was large on me and so I assumed picking up 120 stitches for the hat would be plenty. It's a super cute hat, but again, a little condomy (although not as condomy). I think i just look silly in hats.

The photo on the left is the first condomy hat. This one needs a good home on a smallish head. The photo on the right is the mostly finished Clamber hat (ends aren't woven in). It's not bad, but it makes me look like a conehead (I think, but i'm fairly critical of myself). So I need input? Cute or conehead?