Does this scarf look totally dumb?
Five days of wearing a sartorial classic
I love the look of a scarf, but the story always ends the same.
At first, I feel fabulous. But as soon as I turn my head or breathe or live, the damn thing shimmies right off. And then I feel stupid.
I’ve tried securing it with bobby pins, and headbands with grippies. No dice. Is my hair too slippery? Did I not do enough tummy time, resulting in a flat head?
I mean, if I can blame my parents for this, why wouldn’t I?
I gave up on scarves long ago. And then, The Algorithm served me this:
Could I try again? Could I be this chic and sophisticated? Only one way to find out.
Enter: The 2025 Great Scarf Dare
One week, five different scarf looks. Because there are many ways to style a scarf, I started with Easy Stuff and moved up until I hit Level Audrey Hepburn Breakfast at Tiffany’s.
Step One: Procure two vintage silk scarfs.
Once I said the words silk scarf aloud, my social feed flooded with them. Buy this! Buy that! Buttery soft! You need one in every color! Sorry, Zuck: You cannot influence me to buy a new “silk” scarf when there are thousands of vintage silk scarves looking for homes.
I looked up vintage Hermes scarves on The Real Real, and immediately shit my pants. I can get pretty creative with my accounting, but the idea of writing off a $500 Hermes scarf felt a little too David Rose.
One thing I noted about Hermes scarves: they are HUGE! Whereas an average bandana is 22” x 22”, a true scarf clocks in at 34” x 34”! I believe Big-Ass Scarf is the technical term. I couldn’t help but wonder: Did my series of scarf woes all come down to size? Had I been using a doormat when I should’ve looked at area rugs?
I ended up finding a vintage silk bandana and scarf on Poshmark, both in colors I know I wear frequently.
Day 1: Accessorizing My Purse
The easiest way to incorporate a silk scarf? Tie it on your bag.
I recently saw a woman carrying a Luis Vuitton bag with an expensive silk scarf tied to it. I’m not proud to admit that I felt an initial whoosh of judgment— like your $3,000 purse needs a $500 accessory? Okay, Jillian. It feels like buying outfits (plural) for your dog, or gifting a sterling silver Ralph Lauren baby rattle.
Are we really running out of ideas for blowing money?
Anyhow, I tied the bandana scarf to my brown leather bag. Honestly… I liked this! It felt like an easy way to add dimension and polish to a boring look.
I won’t be buying scarfs for all of my purses (they can use their own allowance for that), but if I want to elevate a boring outfit, this works!
Day 2: A Girly Hair Bow
T-Swift’s Eras Tour brought girlhood to the sartorial forefront. Look, flouncy pastel pink skirts and little bows and ballet-inspired everything is great!
For someone else.
Even as a girl, I struggled with girly things. I asked for Barbies, and then never played with them. I hated tights, hot curlers, itchy velvet dresses. Affixing a scarf to my pony tail at 42-years-old? Hrm… I just don’t know about that.
Here’s what it looked like:
Because it’s behind my head, I couldn’t see the bow— I kinda set it and forget it. Much like the scarf tied on my purse, it elevated a boring outfit.
But the look is… just not me.
I did get my one-and-only scarf compliment: My 8-year-old daughter said I looked soooo pretty.
Day 3: The Jaunty Neck Scarf
I’ve tried tying a bandana around my neck, but it never looked quite right. The right fabric is key: You either need a true vintage cotton bandana that’s more washed up than Tara Reid (sorry, Tara! You were great in American Pie!), or a silk one. Otherwise, it can go all rigamortis, and I don’t care for getting inadvertently poked by my scarf.
There are many ways to tie a bandana, and I went with this because I didn’t feel like googling a how-to. It looks… okay?
I was about to meet a friend for coffee, so I added my favorite jacket (bought mine second hand on Poshmark, and it’s amazing!) and a pair of sunglasses. With those two additions, this scarf look went from fine to fabulous, if I do say so myself!
It’s true what “they” say: Styling your clothes makes a difference.
Day 3.5: Same Look, Bigger Scarf
Yes, Molly, the bandana worked. But how would we feel about a Big-Ass Scarf?
The BAS looked okay with my chambray shirt. But with the cardigan and sunglasses? Call me Muffy or Buffy and meet me at the club! Maybe this is how I could one day feel chic at the airport?!
Day 4: Audrey Hepburn-Inspired Head Scarf
Four days into my challenge, I felt ready for my chic “riding in a convertible down the Amalfi Coast” moment.
I watched this TikTok for tips on tying the scarf in a way that didn’t make me look like Strega Nona.
I did feel pretty stupid until I put on the sunglasses. And then I felt okay! Off to school we went!
What I liked: The scarf kept me warm on a deceptively cool morning.
What I hated: Everything else.
Within two blocks, the scarf began slipping backward. I kept pulling it back up. It shimmied its way back down. We fought allll the way to school (.6 miles), then allllll the way to the Co-op (.4 miles) where I planned to pick up groceries. As soon as I walked inside and removed the sunglasses, I morphed from a White Lotus extra to a member of Fiddler on the Roof’s ensemble cast. By the time I hit the produce section, the scarf worked its way off the back of my head, finally resting around my neck. Like a regular scarf, where I left it.
How a person could keep a scarf in place whilst riding with the top down, I’ll never know. It seems like something straight out of the movies, which is why I’ve probably only seen it in the movies.
I’ll stick with a baseball cap.
Day 5: Turban
Now that I’ve stumbled into the scarf content algorithm, I keep seeing new exciting ways to wear a scarf. For example, a turban.
What hoped for? An I Love Lucy-inspired housewife vibe.
What I got:
This took me several tries and too many long, boring YouTube tutorials. Eventually, I enrolled my friend Marge’s help— turban tying required two people.
I couldn’t decide if I looked as though I was about to tell Peewee Herman to visit the Alamo, or like a grandmother who constantly prods you to Eat! Eat! You’re all skin and bones!
I liked neither.
Then, my husband emerged from his office and froze. I could see the gears turning as though he was trying to figure out what to say without insulting me.
Are you thinking I look like the kind of lady who chases her granddaughter’s suitor out the front door with a broom? I asked.
Yes, exactly, he responded with palpable relief.
I did end up wearing the turban while cleaning our kitchen, followed by picking up dog poop from the backyard. I felt slightly more chic than normal (not saying much), and then I stepped in dog poop.
Later, I walked to lunch with some friends. As we walked, I told my friend Virginia about my scarf challenge, and asked what she thought of the turban.
I guess I can get behind it if it’s a challenge, she said.
Since I’d finished my chores, I decided to retire the turban. I tied it around my neck, where it stayed for the rest of the day.
What’s your go-to option for “elevating” an outfit?
Fun. And Strega Nona!
I vote for the neck scarf with the small knot at the front. DO NOT wear the head scarfs before you become a great, great grandmother.