I did a post recently elsewhere about a female comedian and her very intentionally quirky clothing style. I'm guessing she likely has Jupiter or Uranus or related influences on her Rising Sign or first house.
She dresses like a Kibbe Flamboyant Gamine and sometimes has crazy outfits that actually work anyway, but I think she could have a more flattering haircut. Flamboyant Gamine does better with an asymmetrical haircut.
I have Uranus strongly aspecting my Rising Sign and I do better with an asymmetrical haircut (I'm a Soft Dramatic, not a Flamboyant Gamine). I have wavy hair except for one straighter patch somewhere and an asymmetrical haircut helps cover that quirk. My face isn't perfectly symmetrical. One eyebrow is a little more arched and pointy than the other and I typically part my hair over that eyebrow if I'm parting it.
Uranus is associated with asymmetrical stuff and with eccentricity or the unusual. See also:
I also have Jupiter in an air sign in Exact aspect to my Rising Sign. Jupiter is a bit of a clown and is associated with brights like fuschia and orange. So I frequently wear Earth tones or various shades of blue or teal with brights like fuschia or orange. No, no color typing system I've ever tripped across ever says this combo makes any god-damned sense for anyone ever.
Jupiter is expansive and associated with large scale. I'm a big woman and I do well with bigger patterns than some women can pull off.
Flamboyant Gamine are petite women who do well in fairly large scale patterns, like polka dots and stripes that are anything but subtle.
Jupiter very much describes the way actual clowns dress, with oversized shoes, bright colors and humorous elements to the outfit.
So I spent my whole life trying to figure out how to power dress and get taken seriously and then completely accidentally stumbled across the fact that an injection of humor into my outfit makes me more approachable.
I don't have the career success I want and the income I need. I look at that and think "No one takes me seriously!"
But the reality is I tend to intimidate people and get mistaken for being more upper class than I am.
I was homeless and got a Tweety Bird sweatshirt for free from homeless services (or maybe for something like a dollar from a second hand store). It was a big bright yellow bird on a dark sweatshirt. To my SHOCK, people were saying they wanted to buy my shirt and people were making conversations with me because I was wearing it. It was a conversation piece.
I also was more approachable in a sweatshirt with an embroidered city skyline in bright rainbow coloring.
It resonates with my thoughts about a different problem space: I spent a lot of time in online forums and generally speaking if you want to deal effectively with social stuff, you want to put people at ease and be approachable.
But it never occurred to me to apply that to my wardrobe. I mean I feel stupid because dressing for success is a social thing and about social perception.
At my first paid job, I was a cashier at Kmart and required to wear a jacket, so I show up on my first day of work in a humble, inexpensive cotton suit my mother sewed to meet dress code and the female manager gives me the stink eye for dressing better than her and looking like the owner's daughter rather than an entry level employee.
So at my first break, I rolled up the sleeves, pulled a belt out of my pocket and belted it and unbuttoned a few buttons to make it more casual because I looked like I was seriously mega power dressing and out dressing everyone at work.
I wasn't trying to do that. I grabbed something comfortable that I liked wearing that was not expensive which complied with dress code.
Anyway, my tendency to wear statement pieces with strong patterns surrounded by plainer pieces can come across as clownish if you mess it up in some fashion and I saw some show, maybe What Not To Wear, and they talked about Elle Woods of Legally Blonde dressing humorously in some of her outfits.
Some article said she had something like forty hairstyles in that movie. Most women wouldn't know how to do forty hairstyles for themselves.
That's the kind of thing that takes time, effort and expertise and can subtly weird out everyone around you for reasons no one can quite put their finger on.
So arguably you can view Elle Woods as dressing humorously to try to not intimidate people. Because she's some "ditz" who decides to go to Harvard Law School to get her boyfriend back and pulls it off. She has a 4.0 and is being treated dismissively like "Harvard Law won't care about your perfect score in history of the polka dot." and told she needs some high score on the LSAT and she needs a backup plan because she is not likely to get into Harvard from some no name school and her fashion degree and she's like "No, no backups. I'm going to Harvard."
I LOVED that movie when it came out. I'm someone who can cast astrological charts (or could decades ago) by hand because I had more college math in high school than a lot of people with bachelor's degrees and everyone thought I was a DITZ with my ditzy hobbies and lavender clothes.
And one of the highest ranked students of my graduating high school class who won a National Merit Scholarship to one of the top two universities in my state. And then turned it down for various reasons.
And I've never regretted that I turned it down. I didn't set "Scholarship to UGA" as a goal. I just woke up one day and had a scholarship because I was one of the best.
And it's not like I didn't work at school. I did. But I was also sick all the time and suicidal and between the two sometimes just didn't do certain assignments, so I did not have a 4.0.
But most people work at getting something like a National Merit Scholarship as an explicit goal and it's rare to turn it down. In all the decades I've been online, I had one person tell me they also had been awarded a National Merit Scholarship and turned it down and they told me that to say something like I was such an inspiration and made them feel better about their choice because they had baggage about it.
I don't have baggage about that decision.
Anyway, I tend to intimidate people and perhaps like Elle Woods, dressing a bit humorously turns out to be a way to put people at ease and I stumbled upon that fact and have cared a lot less ever since about "dressing down because I'm poor." (It's not that simple. I'm poor and I dress the way I dress because of my medical situation.)
My mother's mother was from a low level noble family that sold the title and she was visibly bothered by taking hand-me-down clothes for me from a friend of hers and never got the real career she wanted and it's likely baggage from her where I imagine I need to dress to impress and imagine I don't have a career "because people don't take me seriously, damn it!"
If you have a Jupiter influence on you Rising Sign or first house, perhaps you also need to get over it and embrace playing the clown to some degree. And that may include wearing brights and wearing oversized, "silly" patterns instead of trying to be all serious and conservative all the time.
Footnote
I will add that ditzy Elle Woods wins her case because she knows hair care. And no one can argue it because they mocked her about how it's been established she was in the shower.