We recently got the news at my workplace that we are welcome to wear jeans most days if we so choose. I’m betting that many of you just said “oooh, lucky!”    Yes, I feel fortunate to have the flexibility and atmosphere to be casual.  Yet after nearly three decades of business attire, this announcement has me a bit… befuddled.

Mind you, when Business Casual became a thing, it was pretty easy for me to happily shed my suits, double-breasted suit dresses (yes, I had one or two), and my nylons.  Especially the nylons. Hate those things.  But this adjustment seems to be posing a bit of a challenge for me.  First of all, it has forced me to take a closer look at my denim collection in my closet.  I have the old beat-on pair of jeans that are reserved for projects like painting or yard work, and the pair I purchased a few years ago when the distressed and torn look was just becoming a thing and I wanted to feel trendy – neither of which I can wear to work.

Beyond those, I have two pairs that I’ve had for at least 10 years (perhaps more like 15+), previously referred to as my “nice” jeans for those used-to-be-rare Casual Friday occasions, because they look good with heeled boots and a blazer.

Other than that, I have the basic Levi’s dark blues that apparently no one wears anymore, one private label brand that are not especially attractive, and a pair of Eddie Bauer that I purchased at a consignment store.

Hmmm, not exactly anything that screams funky, fun, or on-trend.  All of the jeans in my closet are there for two very important reasons: 1. They fit (more or less), and 2. They are at least moderately comfortable.  One would think that all jeans are comfy and look great. WRONG.  Ask any R.W. how easy it is to find well-fitting attractive jeans and the response will likely include an eye roll and a groan.

Guys have it easier. They find a brand they prefer – like Nautica, Levi’s or Lucky, pick their preferred shade of blueness, find their waist and length size and bada-bing, done.  They then have two varieties of jeans in their collection: stained with paint, oil and grime, or those they can be seen wearing out in public.

Not so easy for us women. As with all of our clothing, jeans seem to need to make some sort of statement, or carry some style.  And so, with visions of going shopping for cool new jeans dancing in my head, I started to browse the trends.  My very first “h-ll no” was Mom Jeans.  Sorry, ladies, I lived through the high-waisted, narrow legged version the first time it came around (was that in the 80’s?) and it wasn’t attractive back then either.  Mom Jeans have the potential to only look good on a 20-something who weighs 110 pounds. No good can come of putting a pair on someone over the age of 50.  You don’t want something that accentuates all that we hate about our mature bodies: menopausal muffins, heavy hips and thick thighs.  When I hear Mom Jeans, in my minds eye, all I can see is the iconic SNL Skit.

According to Harpers Bazaar, there are “13 Types of Jeans to Try This Season”. Oh, my.   I’ve always liked the look of a bootcut, yet apparently now I need the “new” bootcut, whatever that is.  Harpers also surprisingly encourages matching denim in full outfit combinations.  The other day I had on a pair of jeans, grabbed an antique jean jacket I’ve had since before my son was born, and left the house worrying that I looked like I had on a Canadian Tuxedo and was dangerously close to O-D’ing (Over Deniming).

I perked up with Harper’s suggested flared jeans – heck, I rocked those in the 70’s – until I saw that this is what they meant. 

Even if I could get those over my thighs, I’d probably trip on the ruffles.

But wait, it gets worse.

The Roll Down??  Holy 90’s Flashback… and not a good one.  Again, a style that only looks good on someone young and thin as a rail.  Then the top prize of all, the Double Down look.  I have no words for that one.

Ok, so apparently checking out the hottest new styles online is unrealistic.  As an alternative, I’ve begun try to update my denim look by turning to old retail friends like Macy’s, Cato, DressBarn, Kohls – you know, those shops where R.W.’s can actually afford to buy clothes… but so far I’ve seen that the most common styles are Skinny, Boyfriend, and Cropped/Ankle length. Really?   Skinny jeans??  Those look good on about 1/16^thof the R.W. population.  The rest of us prefer to NOT look like we are walking on stuffed sausages — and p.s. we enjoy being able to breathe.   Boyfriend?  Ok, at least breathing and comfort are more possible, but on a mature figure the Boyfriend jean can end up looking blah and baggie and ill-fitting.  As if instead of climbing into our Mom Jeans, we threw on our husband’s Dad Jeans.  And cropped pants are cute in the summer, but when the cold weather hits and you have to add socks and boots, they end up just looking kind of odd, like old school high-waters. At least on me they do.

Maybe I’m being too picky. After all, jeans are supposed to be casual, comfy and easy.  News that I can wear them more often should be a good thing.  Is anyone really going to care what they look like as long as they are not torn and stained?  No, probably not.  And I always have my back-up of a whole lotta dress pants, skirts and business casual items waiting in the wings for the days I give up and go back to them.  Some days I’m sure I’ll do just that, because those outfits hang in my closet like grown-up Garanimals.  After years of accumulation, they are the no brainer option.

Perhaps the issue is not necessarily the jeans themselves, but the full ensemble.  The cute and casual work thing requires some sort of appropriate top that strikes a balance between an old T-Shirt and a silk shirt.  And oh boy, don’t even get me started on how I look in flannel.

I’m sure that soon I will embrace and love our new casual atmosphere, and my dress pants and skirts will become lonely.  I’ll hop comfortably on the train just in time for the next new work attire standard to go into effect — who knows, maybe next it will be acceptable to show up in yoga pants and slouchy hoodies.  If that’s the case, game on. I’m ready.