Originally, I classified myself under "Lonely Loner Laboring" because I spent time alone on my bicycle. People are buzzing about how Southern California is shifting to a more bicycle-friendly landscape. There are bike lanes and sharrows on more of our roadways. Either I'm connecting with more cyclists, or there are more people out there on bikes now.
Just when I think I'm alone, I look around at a red light and Voilà, there are two more cyclists coming up behind me. I love it. Also, I rarely ride alone now. My dear husband is usually right there with me.
Reflecting on my classification scheme (don't get mad, it's what scientists do!) I realize now that with more diversity in cycling, it's useless to try to fit cyclists into boxes. Many of us crossover into more than one category. When I wrote that post, I had just started riding with Riverside Bicycle Club (for three months) and I was upset that folks were peer-pressuring me to ride in spandex.
I read a lot of articles from Bicycling magazine, which is great but also tends to push people to buy stuff. You definitely don't need to buy stuff to ride a bike, with the exception of a bike. It's also good to have lights, a helmet, and some reflectors. But other than that, wear what you want! There are many creative solutions for commuters.
The biggest apprehension I hear from people that are unsure about riding a bike to school or work is that they will mess up their hair or outfit. That's where a little creativity comes in! For me, it is easier to maintain a haircut that looks great straight out of a helmet. When my hair is longer, and in the cooler winter months, I use a silk scarf under my helmet to create a hair-flip. You're not going to come out of the helmet looking this glam, but a haircut like this can get smooshed under a helmet, dry a little bit smooshed and come out looking wavy and soft. The longer version is best for winter, covering a little of your neck and ears. The shorter version is good for summer, to keep your neck cool.
Another hairstyle that worked great for me was a pixie. Now I understand that this hairstyle may send your boyfriend or husband into a tailspin, but it's not on his head! You will want to stay cool, but still look cute and then this haircut is for you! It was great for me when I was doing lots of cycling AND running. Just enough hair to dump a cup of water on it and cool off, but not a mop of hair to trap the heat in.
Another thing I consider when I commute is not wearing light-colored pants. I got lots of great colored jeans from Express (and the Goodwill), some of my favorites right now are Gloria Vanderbilt. Obviously, from the picture you can see that Express jeans are for when I'm leaner and the GV brand is more accommodating to a curvy frame. I wear tall-ish socks and tuck the bottom of the jeans into the socks (in the Winter) whereas in the summer, I roll up the bottom of the jeans for a capri-style that's a bit cooler for my ankles. If you get a grease-mark on a dark pair of jeans, it isn't as noticable. And if someone does notice, just tell them that riding a bike is awesome. Say proudly, "yeah, I bike to work."
As for shirts, I rock a tank-top as a base layer. I don't wear a sports bra for commuting, but a regular bra with a camisole-built-in-shelf thingy is a good combination for all-day support. In hot months, I will wear my reflective vest directly over the tank top and put my work shirt in my backpack. In cooler months I wear my reflective vest over a button-down shirt. I don't mess around with safety. Even though I call these my "dork vests" I feel like it's a seat-belt. Something that is pro-active. We saw a guy riding with one of these last night, he had not fastened it in the front, so the vest was billowing around him and it really looked like an angel was flying along with him. He wasn't even riding fast, but he looked like he was because of his vest flapping.
I have written a lot about shoes, and the only thing I will say is that I always tuck in my shoelaces. The last thing you need when you're riding in traffic is to get your shoelace caught in your chainring in the middle of an intersection. I've ridden in sandals, sneakers, cycling shoes, and boots. I've not ridden in high heels (pumps) but that's because I don't really wear those. Not to say it isn't possible. The only thing to be wary of is that if you're wearing platforms, you might want to raise your seat up accordingly, or if you're wearing flats (to the point of Barefoot shoes) you may need to lower your seat.
I tried the lifehack called Penny in Your Pants to ride in a skirt. My commuter friends said it looked like I had balls, so I prefer to ride in a skirt with cycling shorts underneath. It is fun to ride a bike in a skirt, but doesn't work well in a pencil skirt. I have some pencil-ish skirts with stretch and a nice slit in the back that can work, but more A-line or even circle skirts work better. The thing I liked about "Penny in Your Pants" is that you don't have to buy stuff to make it work. And that's what I love about commuter cycling style. It's not about the look, but you don't have to look awful. It's more about creative solutions to adapt to the lifestyle.
However you ride, the important thing is that there are many types of cyclists. You don't have to fit into a box to call yourself a cyclist. You don't need a $200 kit. And if you don't know what a "kit" is, then don't worry about it. Just ride.