You look great in your end-of-summer outfits, Carter. And I'm with Angie -- these all look casual enough to pass muster as casual to me, even if some nutty folks are wearing bathing suits!! (SHEESH!!!) Or maybe the word is not casual -- but effortless and relaxed. You don't look like you are trying too hard (whatever that means). You look comfortable. I think that is key when trying to set the sartorial standard. As long as you look comfortable in your own skin, others are less likely to feel threatened by your dressing more nicely than they might be. If that makes sense.

Love your idea of a challenge as well.

I need to think a bit about what my personal one would be. September is always a busy social month for me so I have lots of opportunities to dress up a bit. I've started to incorporate some of my great NAS buys into rotation, too, so that is not an issue. So I will mull on it a bit and look forward to seeing what everyone else comes up with!

I love all your looks!! I do agree with Angie - wear your wonderful clothes. I think we have gone too far if a swimsuit is okay to wear to dinner at an upmarket restaurant... I am all for casual clothes but I think we need to respect occasions too.... I have this battle with the three males in my household constantly, mostly the younger two.

I will think about a challenge - I have got out of the WIW habit a little - mostly because it is early spring and so changeable. I am still wearing wintery/trans- seasonal clothing in the most part but I am quite bored with them - and it is the light tee with a topper time of year which I can struggle with to match proportions!

I'll pick one too. Although I might wait to read everyone else's choice to see if I want my idea of someone else's before I pick mine. I loved the last one I did. I might pick a different challenge each week. I'll see.

I'm building a career capsule at the moment. I'm up for a challenge once I figure out what I'm going to need!

I love my athleisure/lounge gear, too! I'm not wanting to get stuck in a rut, but I'm sure glad we have great choices when we need/wish to dress this way!

I thought I would take the opportunity to check in. I have been conscientious about wearing the items I identified as wanting to wear. I also made an effort to increase my casual style quotient, but by Friday I was tired and resorted to the old standbys. Habits are hard to change. I will continue to make the effort. I'll also check in on Wednesday.

I read this earlier in the week but didn't respond thinking yeah I'm pretty casual. Imagine my horror when I ended up in running tights, running shoes and a sweatshirt in a restaurant in the swanky part of town. How did that happen? I left my car in a car park and went walking in the morning. After that my SO contacted me to say he wanted to go and testdrive a car so he picked me up and we spent two hours looking at cars then he said let's grab lunch and pulled into a Thai place...I'd been before and knew it was not your foodcourt kind of place ...he didn't mind walking in in his cargo shorts, they didn't bat an eyelid at my running pants but I felt yuck....lowering the standard even for me. Maybe I need to keep an emergency kit of jeans in my car.

Sally, I know exactly how that happens! Good thinking on stashing some real clothes in your car.

Sterling, thanks for checking in. It sounds like you're doing better than I am. I wore one of my items on Wednesday. I've completely lost Thursday. No idea what I wore or what I did. Friday was packing and a 5 hour car ride with the dog (and her toenails) in my lap, so just jeans there. Today I'm painting and cleaning, so when my husband forgot something at the store, I had to UPGRADE to an athletic skort and tank top just to go to Walmart. Perhaps I'm going backwards? Hopefully I'll have more success by Wednesday.