people who don't fail, don't take risks. i do believe one needs to take risks and fail in order to grow. i take my risks in other parts of my life. with my clothes, they have to feel like me. i don't see the point of experimenting for its own sake in clothing. after all, for me, clothing needs to be functinal first. included in that function is making me feel good about myself; second, it needs to project a persona or parts of my persnoa so i can accomplish other goals. eg, gaylene's teaching example, rita's need to project accessibility to her students...

so within this context, i wouldn't participate in a clothing challenge just to participate if i have to leave the house in the outfit (30x30, i'm looking at you). i would if it were a play-in-the-closet day.

it sounds boring, but that's the theory anyway. actually, i'm thinking about taking one dress and wearing it 5 days in a row (with different toppers, shoes etc) to see if anyone notices! if no one says something, i will wear the exact same outfit a few days in a row!

I think I experiment a bit too much for the sake of flattery. I was looking through some old outfits and I definitely have had some crazy layered outfits. That's why date outfits always give me the most anxiety, I need to be flattering.
Probably my most flattering outfits are in my opera capsule. But I can't wear those everyday obviously.

Gosh I hope not. Life would be boring indeed, if we focused on looking good at the expense of ever trying anything new. Some of my best style lessons have been the results of experimentations gone wrong. Also, you've got to keep those creative juices flowing in order to be fully alive - so I say, NO - as a general rule (there will always be exceptions) looking good does NOT trump experimentation!

Shannon, this thread really resonates with me. I've often wondered if I experiment too much - and then the next week I wonder if I'm in a rut of sweaters and pencil skirts!
I certainly have had my share of "fail" outfits, and for the most part I don't bother photographing those (often because I am in a hurry and decide to "make do" with something on the way out the door.) I should know better. Like others mentioned, when I'm stressed, I feel best when I'm wearing a tried-and-true FFBO where I feel confident and comfortable. That's not to say that I don't enjoy experimenting, because I do - but I'm more likely to feel good in my skin while trying something new if I don't have external stressors making me worry about other things AND being concerned about my outfit on top of everything else.
I do feel like I learn a lot from the experiments that don't work. Often something will look good in a mirror, but when I analyze a photograph, I don't like how the proportions look on my body - so I have a better sense about how to wear things differently next time. Or an outfit may look great, but during the day I find myself fussing and fidgeting, a sure sign that the fit is off or that the items just aren't comfortable enough for me. Sometimes I am able to dress more confidently when I know what I really DON'T want to wear!

P.S. Also wanted to say that personally, I LOVE the velvet & lace outfit.

I can't answer your exact question but I will say that looking at your specific posts have prompted/pushed me to be a little bit more adventurous in what I wear and how I wear it.

They have helped me see how to translate styles and trends normally shown on young willowy15 year olds to a mature woman and look fun and playful and still age appropriate.

Having witnessed your style evolution since you started posting, I'd say you've struck the most amazing balance between looking great, dressing your body type, and doing the experimenting that has brought you to the top of the YLF student class.

I don't always have the time or opportunity to reply on all the posts, but I also really LOVED that velvet and lace outfit.

I wanted to add that I think when you stop experimenting in general, you risk the danger of falling into a rut. I dare say, that's unwittingly how I ended up here, with tops that were way too short from several seasons back. I just found it worked, and that was that. Didn't think about what was hip with the new young kids as a reflection of things moving on. Not that we need to reinvent the wheel every week, but dipping into unknown waters now and again is a good thing!
I am in total drapey dress mode this year, and didn't own even one a year ago. Didn't help that my first attempt was deemed 'a paper bag' by the BF! But I went back and bought it anyway, and now it feels so 'me' I don't know how I could have not been wearing this fit all my life! Experiment, grow. Fall back on tried and true when needed, and then experiment again!

I guess it's all a balancing act - experimenting enough so you don't get caught in a rut, but not so much that you end up feeling like someone else.

bj - interesting idea of wearing the one dress 5 days in a row. I'd be interested in finding out how that works for you.

Anna - do you think part of why you enjoy experimenting so much is because you are in a uniform all day?

Kari - "fussing and fidgeting" is becoming much more important to me. Even if an outfit looks good, if I'm tucking and straightening all day, I won't likely wear it again.

Thank you Marley, Moira, Claudia & Mo!

(Claudia - what a beautiful thing to say :))

Hi Shannon --

You are definitely one of the big experimenters around here! That's a lot of creative energy unleashed, which is always interesting if nothing else, right?

I don't have time to read many of the forum WIW, but whenever I catch yours you seem to have a lot of hits. As long as you're comfortable enough with your ratio of hits to misses then I wouldn't worry about it.

I am more of of a low-key experimenter. I generally do what Amiable was suggesting..."Wear colors you're comfortable with, in new silhouettes, or try new colors in your normal shapes, or change up the textures - enough to be 'sorta' out of your zone, but not so far out as to make it uncomfortable?"

If you end up feeling that your fit/flattery goals are getting short-changed by what you deem "misses," you can always alter your process or dial back on the experiments for a while. Good luck!