I’m sure there’s a way to live life without overthinking the smallest, most ridiculously inconsequential things, but I’ve been like this forever and I think it’s just the way it’s always going to be. Shoe shopping, for instance. I recently decided I needed a pair of boots. Like, those short boots. Booties? Do we really call those booties? That’s like calling shorts pantsies, isn’t it? But short boots sounds unnecessarily derogative, like I’m making fun of their height. Look, I’m talking about those boots that are kind of more like shoes, ankle boots, ANYWAY. I don’t really know why I got a message from the universe telling me to get this type of boot, my only explanation is that I exist in a mostly solitary world of repetitive housekeeping and child-Uber tasks and sometimes, frankly, I must engineer my own pleasure.

So I go out to find these boots, but I don’t like the awkwardness of asking someone to bring me different sizes because that makes me feel like an intolerable queen of some foot-specific country (“Fetch me a 7.5, peasant, and be quick about it!”) and I’m too impatient for Zappos so I head to DSW. They put DSW on the sign because it sounds slightly more trendy than its real name, Designer Shoe Warehouse. Whoo, that warehouse comes with a real lame-o feeling to it, doesn’t it? It’s like Dress Barn. Like no matter how cute whatever you buy may be, you’re always going to be embarrassed to admit where you bought it. “Oh, this? I got it at Purse Dumpster.”

DSW is uncool but I love it because I can just try on whatever without having to, you know, talk to another human being. (Although I do always feel bad about pulling out all the tissue and shoe forms over and over then inevitably being unable to get them all back the way they were, I can just imagine the poor employee going through the racks with the same head-explodey sensation I get when I find toothpaste on the mirror again, what is wrong with people.) I found a spiffy pair of boots after a massive amount of dithering over various styles and heel heights, so yay! New boots!

But then I got home with my boots and I realized I didn’t know how to wear them. I mean, yeah, put them on my feet, I had that part figured out, but I was picturing them with skinny jeans — because my idea of embracing fashion is to watch it suspiciously for several years before deciding to give it a shot, long after it’s gone out of style — and when I stood in front of the mirror with my skinny jeans and boots I did not look lanky and effortlessly edgy, I looked stumpy and awkward. Here were my legs, then a sudden transition to boot. It wasn’t really flattering. The word that came to mind was hooves.

Deep down, I know the real problem is that I’m endlessly self-critical and I will never stop comparing my own normal self to Stars: They’re Just Like Us! photos of impossibly gorgeous starlets who are younger than most of the mustard jars in my fridge, and of course I’m not going to look like them with my DSW footwear and stretched-out Target jeans. Still, I embarked on a Google quest to solve my problem and thus contributed to one of the millions of pathetic Yoda-sounding search strings typed by The Olds: “Skinny jeans and ankle boots how to wear?”

There are, naturally, a plethora of articles that address this specific cry into the void, complete with explanatory photos. I learned that one shouldn’t tuck one’s pants into the boot, because you need a break in the line of the leg at the ankle to avoid the stumpiness. Okay then! Cuffing seems to be key, but oh ho ho, not the wrong kind of cuffing. Apparently there are right ways and wrong ways to roll up your jeans, as evidenced by this actual sentence I have copied verbatim from one of the how-to posts I found: This is a cuffing style that you have to be careful with.

Well! Talk about a sentence custom-designed to send a cold trickle of sweat down my spine. This is how a person comes to own 37 identical grey hoodies, because at least if my head isn’t actively trapped in a sleeve when I leave the house I can be mostly certain I’m dressed correctly.

In conclusion, I’ve yet to wear my new boots because I’m scared of failing the jean-cuff challenge and accidentally sending out a suburban white lady gang sign that gets me roped into some sort of yoga battle, contestants forced into frog pose while struggling to clench their buttocks over the staccato outburst brewing from their morning bowl of Kashi “As much protein as an egg, more startling midday farts than a boxcar of lentils!” GoLean cereal, the young Snapchat-savvy audience standing by with their superior ankle line breaks, shaking their balayage highlights in disapproval. I knew this was going to happen ALL ALONG, I’ll be thinking to myself, stamping out a pitiful S.O.S. on the lavender-scented mat with my maybe-cute hooves.

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Jennifer
Jennifer
5 years ago

You have absolutely spoken to my soul, while making me cackle to the point of causing the dog concern. Thank you, I was in need of this :)

I’ll be watching for the unveiling on Instagram :P

Kristi
Kristi
5 years ago

Hooves or not..everybody loves ponies.

Donna Brubach
Donna Brubach
5 years ago

Yes yes yes

Jill
5 years ago

Oh Linda! You have such a brilliant wit! I’ve loved reading your blog the past 10 years. You’ve done a lot of inspiring for this gal right here.

I just bought my first pair of hooves, I mean boot-ies! ugh with the name. However, you really need to check out LuLaRoe. This brand has made me fashionable, confident, and willing to take bold moves with patterns and colors…but totally comfortable at the same time – a MUST at my ripe age of almost 40! :)

If you don’t look into it with me, find another consultant in your area because it WILL change your life.

Wendy
Wendy
5 years ago

I could relate to EVERYTHING you wrote, in this and your previous post. I am 10 years older than you, and I was startled this year to find out that my butt is following the same path as my upper arms (i.e., sinking towards the earth no matter how hard I fight).

I finally got the clue about skinny jeans but haven’t taken the ankle boots plunge yet. I’m taking notes from you, Linda. :)

Laura
Laura
5 years ago

I have attempted the cuffing, and it is not for the faint of heart. Not to mention the probability of scorn from the teenager girls that I live with.

Mostly I wanted to comment to say that I’m thrilled that you are posting here again.

Sharon
Sharon
5 years ago

I like to try out a style a few years after it has gone out of fashion also. Can’t really go wrong with hoodies and running shoes.

Kristen
Kristen
5 years ago

Oh god, Linda! I’ve missed your humor (purse dumpster?!?! more startling midday farts than a boxcar of lentils! (seriously, where do you come up with this gold?)) and your realness in talking about everyday things. I’m so glad to see you are back writing again!

Jeanette
5 years ago

Hey! I love DSW. I am proud to say that 95% of my shoes come from there!

Shelley
Shelley
5 years ago

Too funny. As pitiful as this will sound, “Buy Ankle Boots” has been (my biggest procrastination item) on my to do list for a couple weeks now. And where else would I go but DSW for all the reasons you mentioned? Now, not sure if I even want to “go there” as I know it would painfully unfold exactly as you so hilariously described. Thanks for a much needed laugh and feeling of connection.

Heidi
Heidi
5 years ago

Hahahaha! Every time my coworker wears her booties with awkward length dresses I immediately think “tree stumps”. I hope you figure it out, most everyone I know who wears them…doing it ALL WRONG.

Jen
Jen
5 years ago

Did you ever French roll your jeans when you were younger? My much younger fashionista sister was all “calm down, it’s just French rolling” and it was like a lightbulb moment for me. You can do this.

Also wear thin no show socks. Makes them so much more comfortable!

The blogger formerly known as Warcrygirl
The blogger formerly known as Warcrygirl
5 years ago

All of my shoes are Crocs thanks to a raging case of plantar fasciitis a few years ago. My foray into skinny jeans was by accident as in I accidentally scooped up a pair on accident. No one rocks the Walmart Chic like I do.

Adrien
5 years ago

You had me at Purse Dumpster.

Navigating the Mothership

I have missed you! So happy to have your voice back in my Feedly.

Now questioning my recent cuffing moments. It’s very dangerous out there, isn’t it?

Mary Clare
Mary Clare
5 years ago

Oh, I delight in your banter on the every day stuff! Thanks for the laughs!

Sarah
Sarah
5 years ago

OK, I’m not one to offer fashion advice as I own, like, two pairs of shoes total, but what if you did leggings instead of skinny jeans?

dani
dani
5 years ago

crap. I haven’t been cuffing. you did’t used to have to! I swear, that’s not just me being old. now I need some cuffing links. please advise.

Andrea
Andrea
5 years ago

Lovelovelove DSW. As for putting all the stuff back in the box, in the shoes all perfect like? NO ONE does. Heck, at my DSW sometimes I find two right shoes of different sizes, or a pair of shoes with one being a different size from the other…and of course I’m not the only one who has this happen to, because they always check to make sure I have a REAL pair of shoes when checking out at the register. As far as the ankle boot/cuffing issue, I have the world’s shortest legs. Anything cuts me off at the ankles (even my ankles cut me off at the ankles) and if I cuff, then I look like a toddler in size 3T pants rolled halfway up their legs so they will fit in the waist over their diaper. No help here. But, you do live in Oregon Duck country, as far as I can tell, if you sport anything with an impossibly large “O” or duck and it’s green or yellow, you’ll be fine :)

Annie
Annie
5 years ago

I have missed your words and humor! Staccato outburst brewing…..f’ng awesome

JennB
5 years ago
mcconk
mcconk
5 years ago

I just recently bought my first pair of STRAIGHT LEG jeans in a million years after owning exclusively boot cut jeans (but having rarely worn a boot). Fashion is clearly not my forte. I think the older you get, the more set in your ways and less likely to follow style trends. Which I why I look exactly like what I am: a 51 year old empty nester/divorcee. Congratulations on trying to keep up! I’m sure you are rocking it.

Kathleen
Kathleen
5 years ago

That last paragraph is the best thing I have read all week. Also, I learned to wear my booties last year (at 38) from my 20- something colleagues.. and now I can’t remember and I am scared of the start of winter around here…

Heather
Heather
5 years ago

Could this be a more perfect post? No. I don’t think so. Not at all.

Jessica V
Jessica V
5 years ago

Yes to all that you wrote (and I cackled loudly at the fart commentary), but I have to note that my local DSW has trashcans planted throughout the store so you don’t have to even pretend that you are going to repackage your rejected shoes correctly. They finally got smart about it. :-)

Maggie
5 years ago

Well shit, I have been tucking my jeans into my booties. I don’t know how to properly cuff or even that I was supposed to cuff! ACK! The only saving grace is that I’m 47, all of my friends are about my age and evidently none of us know how to wear booties so as long as I avoid clusters of hip Youngs my ego can remain blissfully ignorant of these kinds of things.

camille
camille
5 years ago

About a million years ago I’m pretty sure DSW was Discount Shoe Warehouse. Am I mis-remembering? Regardless, ghetto, but awesome. Love the DSW!

JanetS
JanetS
5 years ago

Sending you a big (though awkward) hug for this post.

Some fashion trends I will never understand. On a crisp fall day, isn’t your leg freezing from that exposed inch or two of skin and on down to your ankle? What about on a rainy day? I will be sticking with calf-high boots, which I also do not know how to wear correctly.

Kelly P
Kelly P
5 years ago

Yaaassssssss! All of this! I’ve been on the skinny jeans bandwagon (purchased from Target, Old Navy and JC Penney though, obviously diminishing the cool factor) for a while now, but I seriously struggle with the ankle boots. What? How? I just don’t get it. I have short legs! How can I make this work, even with the cuffs?! Eff you, Pinterest!

Ashley
Ashley
5 years ago

So happy to read you again! Thanks for this, I cackled.

Are you into podcasts (and unsolicited listening suggestions)? I just found a new awesome one just in time for an 18 hour road trip. It’s called My Favorite Murder with Karen Kilgarrif and Georgia Hardstark. I’m sharing it with all the cool people I know:) If you’re looking for some new stuff to put in your ears, try it!

P.S. Seriously. So, so refreshing to read your writing again. Hope you are well.

Brenna Jennings
5 years ago

I have embraced my cankles because I love my ankle boots so much — I got the Lucky Bartolinos and have been wearing them with everything. I feel your hoof pain, but if you can find it in you, put them on, skip the full-length mirror if you’re feeling hot and go.

Christine
5 years ago

I had this problem as soon as I got a pair of skinny jeans (like, two years ago, because I take a long time to embrace a trend), because none of my boots were shortish and I couldn’t figure out how to deal with the meeting point. And then suddenly last year it was fine to turn up your jeans again and that was the so obvious solution. (And I don’t give a shit about the right way to cuff, thank you very much. I don’t think anyone is looking that carefully at my ankle area.) And then I bought a pair of short boots – sorry boots, no offence – and now my life is stress free, until the next fashion dilemma. The fact that I still wear boot cuts 90% of the time and nobody sees me anyway is neither here nor there.

Shawna
Shawna
5 years ago

At least you knew the term “balayage”! I hadn’t even heard of it until I read this post, that’s how out-of-the-loop I apparently am!

Shawna
Shawna
5 years ago

Also, coincidentally, last night I saw someone wearing wedges that were very high-heeled – so her toes didn’t go out that far from her legs and her feet appeared to taper down from her legs instead of making a right turn at the ankle – and the wedge material was a dark brown/black that looked like horizontal bands stacked up. I guarantee without even seeing your booties, that they could not POSSIBLY look more like hooves than these did.

Jennifer
Jennifer
5 years ago

“My idea of embracing fashion is to watch it suspiciously for several years before deciding to give it a shot”

This speaks to me! I too purchased booties this month because I thought they looked effortlessly cool. I haven’t had the confidence to wear them yet though!

Kim
Kim
5 years ago

I work on a college campus which means even on the days I leave the house feeling good about what I’m wearing I see my failure as soon as I get to work. Even the girls wearing the leggings/hoodie/sneaker/messy bun uniform look more put together than me.