Been thinking about this all morning because it’s such a great question, Carla, and it’s been so interesting to read about all the approaches—color, shine, prints, patterns, juxtaposing, accessorizing, quirky accents, graphics, and unexpected elements.

And, yet, I’ve always loved to be in shaded neutrals, matte textures, and solids. I lean heavily towards a uniform of jeans and trousers worn with boots and a crew or polo neck sweater topped with a tailored jacket or coat. Unlike most fabbers, I could exist quite happily with a palette of nothing but black and white in my wardrobe. I’m also a minimalist when it comes to accessorizing and “quirky”/trendy/“must-have” items rarely last for more than a few months in my closet. Looking back on five decades of my fashion-following life, my experiments with almost all of the “fun” ideas suggested here have left me feeling like I’m wearing what others “expect”, not what makes me ME.

What makes an outfit “fun” for me is realizing how my “look” can be constantly morphing while all the while maintaining its inherent consistency. My risk-taking and experimenting isn’t about following others’ cues as much as it is refining, honing, and understanding my own quirky preferences and instinctive leanings. Wearing my brooches on my sleeve cuff instead of my lapels feels right as does gravitating to a stark black and white Fluevog boot when my friends wear ballet slippers and floral dresses. I guess what I’m trying to say is that, to me, being lighthearted about fashion isn’t about what I add to my wardrobe as much as it about giving rein to my own impulses and feelings.

Bright colours. Colourful patterns. "Conversational" prints (even in neutrals). Big earrings. Statement shoes. Big colourful glasses. Unusual handbag. Juxtapositions when it comes to styles and fabrics. Glitter hair. Non-neutral eyeliner/eyeshadow. Bright lipstick.

Not all this at once, though.

I’ve never aspired to look sophisticated. My *fun* can veer toward silly. I just I bought the brooch below at a Going Out of Business sale. Haven’t worn it yet, however. Most of my fun is in my footwear. I have problem feet that tend to be happiest in platforms. And with ruffles I may as well look as though I’m flying away. . .

Animals...I have lots of brooches that are animals, specifically rabbits, flamingos, other birds, and cats. I have lots of pendant necklaces with my favorite critters represented. I also have a couple tees with flamingos on them. One with a pelican. Sweaters with beaded ladybugs or butterflies on them.

Pink sneakers. Iridescent sneakers.

It is easy enough to have fun with a colorful, not too serious preppy closet. Especially when I suit up for work. What will help this somber outfit? Critter jewelry !

I’m like TorontoGirl: sedate fun is where it’s at.

For me, “fun” is mostly about incorporating a few trends and making a few spontaneous purchases.

Wow! I go for a walk, and look what happens! What a great list this is providing for those of us who are analytical about their outfits! Lots of ideas on how to inject lightheartedness or fun without treading into costume or sartorial silliness.

-Colour, pattern, texture, shine
-Juxtoposition
-Interesting design
-something new/trendy
-something old/vintage
-intriguing footwear (and apparently there is a disease that comes with this that affects the wallet and closet space - not fun )
-the unexpected (unique jewelery, unusual ways of styling ordinary items, a surprising print or pattern)
-a signiture (pattern, pin, pet )
-drama, drape, movement, 'swoosh!
-attitude, being comfortable and true to one's style self

Did I leave anything out?

Feathered headdress
Cherry headpiece
Attention Horse

You guys are scaring me .

Acceptably appropriate in as many different settings as possible.I'm the fun, the clothes just have to keep up

I found myself nodding along with most of these responses. Including something unexpected: clashing colors, pattern mixing, old with trendy, a silly tee under a proper-looking blazer., feminine with masculine, etc.
EztA: I have not done this but have admired middle-aged women wearing things like dinosaur leggings, My Little Pony sneakers with ruffled lace socks, and sequined emoji shirts. ( well, I have joined that team basting a big sequined emoji face on the back of a jean jacket. The grandchildren are delighted.

I think the key is understanding what is fun to you. For me its usually an unexpected detail - kind of my private joke. If you don't notice my dinosaur necklace, that's fine b/c it made me smile. But for others it's a more vibrant look that makes other say "that looks fun". I can't pull that off w/o feeling like i'm wearing a costume, but have all the praises for those who are wearing the outfits that make them happy.

What's fun for me is something special. Whether it is a scarf, or jewelry with memories, or the fun of realizing that a certain pair of earrings goes with a certain necklace. Or a new pairing of clothing and accessories.

Big smile and a happy head! Flash of adventurous hair colour when I am feeling brave!

Ha! My fun is mostly in my head. It is fun to incorporate "hot off the presses" trends I find in a thrift store, fun to mix high and low (definitely into juxtaposition), fun to try new things and judge whether I like them or not, fun to stretch my limits, and so on. And fun to read threads like these!

I wear things that I associate to a fun memory or place mostly - I like to buy things when I travel for example. A cowboy hat was a recent purchase and it is indeed very fun to wear. I think I got more positive looks from wearing that hat than I have from many other things lately. Of course I was in a Texas tourist town. A graphic tee from a place I've been is another "fun" thing for me to wear. Or just any item I bought while on vacation as it brings back vacation memories I guess.

I am coming at this from the opposite point of view—I like bright, almost pre-school-like colors and loud prints, with lots of polka dots, so I am often looking for ways to tone it down! But I agree with a lot of things here—Shevia's super-astute comment that it's often in our heads (like even when I wear a pretty basic denim dress, my giant cherry dangly earrings make me feel like a member of the B52s when my outfit is actually pretty staid).

But actually, though I am a very strict list-keeper and shopper, I find when I feel like I need some more fun, it's time to shop for stuff with no list in mind—go out and see what fun stuff grabs me. Usually accessories, like earrings or shoes, but a fun top or dress might pop out too.

I love what Gaylene said. I thought something similar - it’s less about adding a color or pattern or accessories, it’s more about just dressing in a way that feels right for you. When I’m wearing an outfit that feels like “me” it instantly puts a spring in my step. There’s just something about it that makes me feel lighthearted and that makes it fun. I don’t plan my outfits much in advance, I’m a very spontaneous dresser. That makes it easier to just go with something that just feels right in that moment. Of course I have combinations I repeat often, but if they feel right then I don’t get bored.

What an interesting question and responses! For me, I would have to say the fun comes with adding in some trendy items, it makes me feel ‘in the know’ when I’m wearing a fringe trend or the exact right combination when generally people know me, I think, as a more serious person. It’s a cliche, but they don’t expect me to have an interest in fashion and personal style.
Since joining this forum, adding fun also means adding some special timeless items that speak to me on a more emotional level and/or almost costumey pieces that finish off a certain look (taking a page from brooklyn’s book there!).
I’ve also always enjoyed juxtaposition (more masculine-feminine than high-low) but that’s so core to me I don’t specifically see it as fun :).

This is a fun (pun intended) thread. I am nodding my head in agreement with so many posts. Overall, I think fun is an attitude I carry with me. I teach first graders and while we have serious learning to do, I expect it to be fun. I dress up more than others that I work with, yet, I still think my outfits reflect a bit of fun. Color, pattern, texture, shine, shoes or accessories make dressing with an element of fun easy for me. Except on school spirit days, I don’t dress head to toe for fun. I have an element, or two. Well, in addition to my smile and arm candy; make that 3 or 4 elements.

I had to think about it. What is fun for me? I can’t relate to most of the posts here - I have a small palette of colors that consists of navy/black, whites, a bit of grey and olive. I don’t wear dresses or print, well with a few exceptions. I’m a plain kind of person. fun for me would be an outfit that feels like me, that expresses my point of view, sometimes against conventional tastes. I’d wear oversized sweater over wide pants or a tunic over silk truck pants, a shirt dress below the knees over cropped pants. May be it is not a common look among 50+ crowd or not the most flattering but it is mine and it is fun. For me.