Stepping Out of My Comfort Zone.

My very chic Manhattanite sister strutted into Chicago wearing these booties the other weekend (she paid full price, I think, but I found them on ridic sale for $99 here):

(Another similar pair is available from hot footwear line ASH here.) She looked so amazing in them. Of course, she had a whole “I’m-from-New-York” vibe going so the whole outfit just rocked my socks off. (BTW, she’s a designer for Mara Hoffmann — um, amazing — and has worked in the past for the likes of Alexander Wang, Kate Spade, Tucker, Haute Hippie, Jane Post, and Oscar de la Renta. To say I am proud of her is an understatement. Women that succeed in that industry are tough as nails and ridiculously talented.) But it made me stop and re-evaluate my boot selection. I tend to play it safe with Loeffler Randall boots (I have a few pairs, but the Matilde is my go-to), Rag+Bone Kinseys, and some basic black heeled booties I got a few years back from Tory Burch. I only recently made the foray into boot awesomeness with the purchase of these IRO booties ($795):

BTW, these are ridiculously painful. I had no idea a boot could be painful. I always associate them with comfort when compared to heels. But I think it’s because the leg opening is so wide, you have no support whatsoever and you’re pretty much just sticking your foot down a very steep incline without anything to hold it in place. OMG. I was pretty much dragging my feet on the ground at the end of the night.

At any rate, ever since I saw my sister rocking those awesome suede cowboy-meets-urban-wedge rockstars, I’ve been thinking of expanding my repertoire to include some unique stunners. First up: the moto boot. I’ve eyed this fashion trend very cautiously. It’s reallllly not in my wheelhouse. I like things a bit more structured and feminine. And yet:

Now, the Jimmy Choo moto boot is sort of the cult classic here (top). But I’m almost favoring this pair of quilted Marc Jacobs (on sale for $697 — shown in middle). And, if you can believe it, the pair Olivia P. is wearing in the top snap is on sale for only $32…!

I also find these Kate Spades a ladylike twist on the moto style ($398 — perhaps more my speed?!), although the price on these Inovos ($155) is a bit more palatable:

And yet: Mila Kunis, Gisele Bundchen, SJP, and Olivia Palermo also own the Matt Bernson Tundra, yet another take on the moto boot ($385):

Love that the top folds down and that it’s line with soft fluffiness.

Sigh. And at the same time, I have been seeing Reese Witherspoon sporting all of these adorable looks with low (often suede) ankle boots — do you follow her on Instagram?! She’s one of the only celebs I follow, and I’m obsessed.