Out on a Limb.

OK.  There are some things that I inexplicably like, and yet — when I imagine actually wearing them — I think my husband and my friends would look at me quizzically and I’d feel a leeetle awkward.  This was the case with my Missoni turban, and, when I first tested it in college, dark nail polish.  (I’d like to point out that I was way ahead of my time on the dark polish, but both my roommate and my then-boyfriend, now-husband cringed.  This was back when red or pink were the only palatable shades.  I’m sure that now most of us can’t even remember a time when everyone and their mom wasn’t wearing Essie “Wicked.”)  I will also shamefully confess to purchasing a pair of lace-up-in-the-front booties from Intermix a few years back, coddled by a pushy saleslady, only to leave them in my closet collecting dust for two seasons.  Anyway, we’ve all been there.  I’m reminded of a time when I was about eleven and very into “Baby Sitter’s Club,” a boy named Enrique in my class, and pretending to be cooler than I was.  I remember liking one book in which Kristy describes her outfit as an oversized baseball jersey, leggings, and keds.  (By the way, just to set the record straight, Kristy was not even my favorite character in the BSC — I think I wavered in loyalty between Claudia Kishi and Mary Anne Spier.  Claudia was rad, had her own style and an obsession with bad junk food, and was dramatically misunderstood by her family — a true injustice in my eyes.  Mary Anne was “painfully shy” but had a babe of a boyfriend, and this made her naturally bad-ass.  Stacey was cool but had diabetes, which was apparently the worst thing that could happen to anyone ever and was a constant source of tension in the book.  And Dawn was a weirdo from California.  No one liked Dawn.  Even her name sounds like a washed-up country singer with poufy bangs.)  At any rate, I reallllllly realllllly wanted to recreate Kristy’s sporty-cool look.  I remember putting on a jersey-style night-shirt I had (like, it was supposed to be a night-gown) with some leggings and a pair of Ked-like sneakers and traipsing down to the kitchen.  On my way, I began to realize that my mom would never, ever let me out of the house like this.  I started to cringe a little myself.  When I arrived in the kitchen, I looked at my mom expectantly and, unable to play it cool, blurted out: “Mom, can I pleeeeease wear this out!?”  I can’t remember exactly what she said, but the end result was me putting on something slightly more normal.  (Which, in the early 90s, was probably acid wash jeans with a stretchy waist band, a sweatshirt, and a scrunchy.  As I said, something way more normal…)

All this to say that I know the feeling of trying to pull something off and feeling ever so slightly hesitant about it a little too well.  I admire my sister Christina for lit-er-ally (to be read in the voice of Rob Lowe’s character from Parks and Rec) not caring what anyone thinks of her outfit.  She will wear perforated leather shorts with tights and suede booties to a country club; a dramatic fur-and-leather coat to a tea;  a full-length tiered ball-gown type skirt to the opera; you get the idea.  She just rocks.it.out.  She has her own thang going and no one can mess with it.

Part of the problem is that she actually looks awesome all the time.  I, on the other hand,  probably make a lot of missteps.

But anyway, this post is about some items I reallyreallyreally like but that evoke that feeling of “OMG, Mom is never going to let me out of the house like this.”  First up: joveralls (Le Frame, on ridic sale for $87):

Yeah, I said it.  Joveralls.  (AKA a staple in my favorite look from third grade: a pair of Gap khaki joveralls with a lime green mock turtleneck tee.)  I want to wear these pool-side with a camo bikini (again, weird, probably — $39 for top; $34 for bottoms):

And my Chanel espadrilles (similar style to my own available here for $865; get the look for less with these) and Illesteva mirrored shades ($177):

Another strangely attractive item: this FINDS “As If!” sweatshirt (on sale for $25; Clueless was like the anthom of my early teen years) with the pink Wildfox shades I’ve been dying over ($179), my favorite distressed J. Brands ($172), and loud Kenzo sneakers ($240):

Finish with a Balenciaga tote ($1,945) — I have always wanted one of these cool downtown bags.

And, lastly, these chunky lucite frames (Thierry Lasry, $435) with a cookie monster-esque faux fur topper ($150); black skinnies ($261); and highly impractical Isabel Marant booties (on sale for $861):

OK, there.  I did it.  What things do you embarrassingly covet?