Janet, the socks are from Out of Print. Pretty sure they still have them…I love mine so much I’ve replaced them twice.

CJH, those T-shirts sound fun; I want to get the “free hugs” one for my son, but he isn’t any more likely to wear it than I am—even though we’d both laugh (the right way) if we saw someone else wearing it. I like Chucks worn humorously/ironically.

Nuancedream, your outfits are so energetic and fun, they already make people smile without an extra “joke” piece added in.

Janet, lol about the orioles and how often you get to wear them!

Like Bijou snd Angie, I have a number of dog themed things. I know my red Fair Isle Scottie sweater is funny because I saw a character wearing it on Saturday Night Live a few years ago. The Scottie in a tam o shanter is especially silly. I might have a Jack Russell sweater on the way…

Mary Beth, that one I call avant garde!! Love the purse!

I love this thread, Carla. It makes us really think about the categories, and it's really fun to see others' responses. I don't really feel authentic in clothes that are too whimsical or literally conversational. Which I guess explains my difficulty in finding graphic tees that call my name. The kitschy holiday stuff is totally out of the question for me; definitely no Christmas ornament earrings or antler headbands here. And we don't even decorate our home for the holidays, so I guess I'm consistent there. Though we have done some lights outside in the past and talk about it each year, when the dark days drag on for months. Like Cat2, I don't even like dressing up for Halloween. I have done it in the past, but now I would rather skip a party than wear a costume to one. I do get a kick out of seeing creative costumes, though. I'm not without a few whimsical wardrobe items. I have a small collection of dog socks, which I occasionally wear, hidden by pants and booties. And I have a pair of owl-print pajamas, the pun of which escaped me until I had worn them a couple of times--LOL! I made a dog-print t-shirt that I really like a lot (photo below from 2016).

Oh, I forgot, I have this bag. It counts, right?

Not in a obvious, thematic or Word art way, but sometimes yes I come up with a combination that makes me chuckle and that I know some friends might "get" is a wink or a bit ironic/sarcastic. I really can't think of any good recent examples though! When I was young and worked in a sort of... fashion-free environment I did wear some outfits in a kind of ironic/costumey spirit. Like blue plastic Birkenstock clogs worn with comfy sweats for a night shift. The joke being I knew the shoes weren't "real clothes" but I was wearing them anyway. Or showing up for Christmas night shift with Christmas bows on my head. It was kind of situational, an expression of self in an environment where I already stood out more than I was comfortable with but where there also weren't any strong norms to meet, so I felt free to goof a little bit in a kind of send up of myself vs. the environment.

I used to have more quirky/twee/kitsch items in my teens and twenties, but that side of my style seems to have diminished. I think the rise of online shopping and print-on-demand clothing companies -- basically, the increased availability of quirky graphics -- has made them less appealing to me. There's something different about serendipitously finding a cute, humorous piece at a thrift store or boutique vs going online and browsing hundreds of designs to find something that feels cute and humorous...

I do wear Christmas earrings on the odd occasion and enjoy that. That’s about it! I’m not very amusing I think.

Hush. . .is somebody calling my name? I was just thinking the other day that I've never had an Ugly Christmas Sweater -- and I kinda want one. Not gonna seek one out, however.

Before my daughter left for college, I used to dress to blend in so as not to embarrass or horrify her. Now? I have been know to buy stuff just because they are ridiculous, and why not? See especially the Jeffrey Campbell fog boots and the white Crocs with the ridiculous platforms that make my feet look HUGE. But maybe it's because they are 1/2 size too large since the sparkly platform Crocs fit a bit better. The blinding sparkles in the Michael Kors boots and the joggers aren't really captured in the photos. . .

I still dress reasonably respectably when I will be seeing clients, but I feel like some of my current sartorial preferences may be a backlash to the whole Dress for Success thing I had to go through when I was a young professional. And after all, DH and I have collected seals for many years but not so many recently because how many hundred can one have and still have room to live? Umm, how many people do you know with not one but two pairs of seal earrings? One is a Christmas pair so I better get them out so I remember to wear them.

@ DonnaF - I love your attitude! I find that there is something subversive in sartorial humour that I enjoy - especially when I’m not known for having a sense of humour!

*runs off with Mary Beth’s chicken bag, Bijou’s ‘Hello Kitty’ bomber, and Christina’s ‘Cat Person’ sweater…*

@ Synne - interesting thought regarding thrifting…

I like a little silliness in my wardrobe!
Holiday themed earrings and socks.
Holiday pins. Headbands. All in good fun. Sometimes all at once-but usually one or two pieces at a time.

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How so, LisaP?

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@ Bijou - glad you brought the term ‘whimsy’ to the conversation. It encapsulates the fanciful aspect of gentle humour that might be more acceptable/easy when it comes to,fashion.

@ Christina - I like the idea of a visual pun, and the ‘French Hen’ is very dear!

@ Slim Cat, Jules, and JAileen - I can certainly understand the yin/yang aspect and wonder if my current musings on (and desire for) a little sartorial silliness is a response to a recent period of sadness? A way to cheer myself up, if you will.

…kicking myself that I didn’t pick up the Speedo swimsuit with the sushi motif when I saw it

I’m not sure where my long cardigans fall? In my mind they are superhero capes flowing behind me in a swoosh as I walk, however, they are not bold red, bright blue, shiny, etc. Usually, they are nondescript grey cashmere…….

In high school I had a black sheep sweater vest, much like Bijou’s sweater, although my mom picked it for me….

My MIL once gave me a sweatshirt that read…I only eat chocolate on days that end in Y. I wore it because my children liked it more than me….plus it was a gift. I would never have selected it for myself.

@ Staysfit - love the superhero imagery!

Since Staysfit mentioned long cardis, does this count? Swishy long cardi and a Christmas mask (a giveaway from a Thai restaurant!) for a festival!
The sweater swishes like a tail

I forgot to add my fuzzy bags, Thing One and Thing Two.

I like silly socks. And I have a fondness for graphic tees or intarsia sweaters that say odd things. The latest acquisition is a baby blue sweater that has “anxiety” in a prickly font.

DonnaF, your ‘Thing One/Two’ fuzzy bags remind me of one I got my kid for her 10th birthday - but it had actual googly eyes on it (a bit similar to this one but with fur trim). She loved it and wore it to death.

I actually also just bought and wore to a rare dinner party these mismatched socks, which i guess are a bit of whimsy? But I would have preferred a matched version, I just liked the pattern and colours and could overlook that aspect. They were a bit of an impulse magpie add to a larger cyber Monday sale order (from a small Canadian business which I recommend called novmtl). I guess I was at least ok with them being a possible conversation piece though.

And yeah, I hear what you said about cheering yourself up, Runcarla. One of the reasons for the goofy workplace combos I mentioned was definitely to cheer myself up. The swimsuit sounds cute!

No, none at all - I'm Sartorially Serious(TM).

Partially fuelled by an upbringing that wouldn't allow depictions of animate beings anywhere (including on clothing) & the need for multifunctional versatility (hello tiny closet in a tiny HK flat!), I have ONE pair of red tasselled earrings that I wore for my Chinese wedding... then every Xmas party since... & every Chinese New Year since... I would have probably worn to my UK wedding too (if my mother had not already provided jewellery). Wondering when else I should wear them before they officially bite the dust (tassels get crooked fast)

ETA: The closest I have to humourous 'clothing' is a packing cube that reads 'Keeping my Sh!t Together'. Was recently rather tempted by some 'Merry Everything!' socks, but red tassels are enough

Interesting question that I had to think about! I love prints and color especially for tops. But, I don’t have any humorous clothing or jewelry! And only one graphic tee with words (feminist message) that I only wear at home! Like Jenni NZ, I am not amusing, more serious personality.

I guess, because well it’s a thing at work ,so I humor the people I work with

@Synne "Avant-garde"! I love it! But honestly... the photo makes the chicken-bag look better than it actually looks in person. I might never carry it again, but I will always keep it. It was a marvelous surprise gift from my baby sister. We were at some artsy store in Chicago, when I saw a chicken-purse, and I laughed over it until I almost cried - as much at the $50 price tag, as at my natural inclination to view rubber chickens in any form as comic gold.

She surprised me by finding one for much less on Amazon, and having it shipped the following Xmas. It has its own special place of honor in my armoire.

Bijou, that embroidered peacock jacket... I'm sighing over how beautiful that is! I have a great love for embroidered pieces. Strangely, I don't think I've ever viewed embroidered clothing or accessories as whimsical. To me, they are serious works of art

I did just remember that I have a pair of skull-and-crossbone earrings that I bought at the Pirates of the Caribbean at Disney World, and a few quirky holiday-themed costume jewelry pieces. And my yodelling hat. So I guess I do have some other stuff that fits Carla's bill for funny!

Everybody... I am really enjoying seeing your humorous and whimsical pieces! Maybe we need a style challenge...