Fashion Wills and Won'ts of 2020

Like most people, I want to feel good about what I’m wearing. I like a great pair of jeans, a nice-fitting top, and a comfortable dress that makes me looks like I’m trying. I’m not entirely tone-deaf when it comes to what’s in-style, but I’m not always listening either. My college roommates described me as someone who would wear sequins with sweat pants--and that hasn’t really changed. I'm 40 now, so I wear a lot of black-on-black to feel skinny, hide stains, and avoid having to make things match. But in my heart, I’m still just an overgrown toddler in red rain boots and an Elsa costume, insisting to the world that this IS appropriate for the family’s holiday photo.

My idea of what looks good is not necessarily on-trend and I don’t fall for what’s new without years of convincing. I’d rather be that grandma who comes to every family gathering feeling kick-ass in the same pair of peach polyester slacks, than force something fashionable and end up like a Labrador in a cone collar, trying to act natural.

I’m also not a big shopper. I typically rely on people-watching to determine what the cool kids are wearing, or at least, what the accepted uniform is for various public places: the outdoor concert, the kid-friendly restaurant with beer specials, the sideline at my kid’s soccer game. Real-life people in my personal demographic are typically more reliable than suggestions that come across my Facebook feed. Some sites are run by moms who have my best interests at heart--but let's be honest; these ladies clearly have much fatter clothing budgets than I do. If I'm paying any more than $50 for any single article, it had better be able to make my kids' lunches and drive them to school without me. 

Other sites apparently misinterpreted my mine-able data as someone who cares about “things no woman over 40 should own"--like a sweater that has pills on it. Really? No shit. This is about function over form, my friend. Plus, if I toss this one because it's old, then it's a slippery fucking slope for the rest of my closet. 

Perhaps my favorite sites though, are the ones that want to talk me into "what's hot" for whatever upcoming season. Sometimes, it's overly-obvious, like: JEANS. Yes. Thank you for that shrewd assessment. Other times, it's something utterly ridiculous, like these pleated pleather pants. Call it vegan leather all you want; I bought a jacket to wear over my bar-hopping clothes from the Charlotte Russe about 20 years ago, made out of that same material. It was pleather then, it is pleather now. I will not be persuaded into paying the equivalent of a car payment for a pair of ugly-ass pants that might melt if I stand too close to a space heater.

That brings me to the following assessment of the fashion advice I’ve gleaned from social media. I say these are my thoughts for 2020, but honestly, what do I know? If you feel like everything I’m about to mention is soooo 2017, then congratulations! You clearly know your shit. And if something I don’t like looks great on you, out-fucking-standing. Rock it like a boss. You know yourself and your audience--just like I know damn well what I will and won’t be wearing in 2020.

Over-the-knee boots. Unless I’m a member of a swat team or Julia Roberts from Pretty Woman, I can’t get on board with boots that breach the knee/thigh barrier. I mean, if we’re not careful, the boot itself will one day over-take us all, until we’re just zipping ourselves into one giant shaft of faux-suede and hopping around like a team of sack-racers. 

Over-sized blazers. While I can get down with “the boyfriend T” and even “the boyfriend jean”, I cannot be convinced that the “father’s sport coat” is flattering in any way. 

Pleated pants. 1985 called and said they’d like to inflate your bottom half like a swollen bicycle tire. You tell them to fuck off. If Kerri Russell can’t pull off pleats in an episode of The Americans, neither can you. Flat-fronts forever.

Statement jewelry and handbags. I’ve always been jealous of ladies who can accessorize, but doing it wrong feels like I’m Mr. T on his way to a parent-teacher conference. I’ve got an engagement/wedding ring combo that says “I’m married”, earrings that say “my sister gave me these”, and a cross-body purse that says “I carry tampons, balled-up Aldi receipts, and a pair of my kid’s clean underpants”. 

High-waisted jeans. Everything I’ve read touts these as the messiah of all denim, universally flattering with a classic aesthetic. This has not been my experience. Blame it on waist-to-ass differential, but I just can’t even with the sizing on these bastards. If I jam my rump roast into one-size-too-small, the rest of me busts out the top like raw biscuit dough. If I wear a size that actually fits the haunches, there’s a mile of zipper inching ever-downward toward my knees because they won’t stay up. I feel like we’re all being conned into some 80s mom's retired pair of Jordache, and I just can't pull it off.

Jumpsuits. I’m torn. On the one hand, my Barbie looked fierce as fuck in a gold foil halter-neck pantsuit back in 1986. On the other hand, I’m 3/4s torso, 1/4 legs—so any garment that connects my crotch to my clavicle is destined to become a front-to-back wedgie for the ages. Jumpsuits are the more sophisticated cousin of the romper, to which I'm adamantly opposed. Either option creates the awkward result of a grown-ass woman in a onesie, with no choice but to fully undress when she pees.

Skinny jeans. It took a decade of brain-washing to convince me these were not just my tapered-leg, powder-blue Guess jeans from 5th grade coming back to haunt me. But the damage is done. I’ve drunk the Koolaid and will continue to wear dark-wash skinnies whether the world still likes them or not, zipped into boots of a sensible height like it’s 2011.

Wide-leg jeans. Oh my flares, how I’ve missed you. For the last few years, I only saw you on worn-out, middle-aged Waffle House waitresses, smoking Mistys and screaming into their Nextels. But according to the Internet, the anti-skinnies are ripe for a comeback—and I am fucking PSYCHED! I’ve read a few tentative descriptions of how to “style” these old friends and how ‘not to be scared of a wider leg’. I assure you. I’m not scared. I retired my last pair of bootcuts just last year, only because they ripped in the crotch and no longer had a top button to help keep the zipper up. The current size of my ass might suggest that high school was a looooong time ago, but when it comes to jeans, in my heart, it’s still 1997.

Leggings. I’m sure there will one day be a movement to abolish the God-given freedom of these elastic-waist wonders. Until then, active wear is one cat we couldn’t shove back in the bag if we wanted to. And no one fucking wants to.

Whatever the hell I want. Now this is always in season and looks perfectly fine, even after several consecutive weeks of red wine and Christmas cookies. Whether it’s 2020 or seven years ago, whatever-the-hell-I-want keeps me looking and feeling like my best self, which is always the greatest way to be.