A few weeks ago, I let you in on a dark little secret: I was hanging out in my home office braless during the work day. I needed an intervention, and I used you to give it to me in the form of my November OOTD Challenge. Here are nineteen lessons that I have learned–or am still learning–from my nineteen days of getting dressed.

1. I have more outfit possibilities than I realized.  Taking photographs caused me to worry more about repeating an outfit than I would if I were actually showing up at an office in the city. Amazingly, I only wore repeats three times, and even then there were slight variations.

2. Getting dressed is a lot of work. I changed three times just to go to the dentist last week. No wonder I’ve been taking the easy way out and avoiding this process.

3. Going through this process is the only way to solve problems. Thanks to getting dressed down to the shoes, I finally figured out that if I sanded down the edges of my dress shoe orthotics, I could be comfortable in my dress shoes instead of wearing my gym shoes all the time. When I avoid the process of dressing, I never have to work through to the solutions.

4. When I get dressed every day, I realize what I need. By wearing a dress on a really cold and windy day, I discovered that I needed tights to match my navy shoes. If I had just thrown on my jeans and gym shoes that day, I wouldn’t have bought the tights that gave me many more options later in the month.

5. It’s okay to buy what I need. Because my husband and I are on a very tight budget right now, and because I’ve been wearing so much lounge wear at home, any clothing purchase has seemed like an unnecessary expense. Getting dressed every day has reminded me that things like tights are NOT a luxury.

6. I want to “need” a dozen coats and purses, but that’s just not me. My current black wool coat keeps me warm and looks okay even though it’s slightly threadbare in places and the lining is torn. Even if we had a gigantic clothing budget, an extra coat would still seem like a luxury to me, and the same goes for purses. Perhaps I approach coats and purses the way the majority of American women approach bras. I wear the same neutral coat and bag wherever I go; they wear the same beige bra wherever they go.

7. I don’t just play it safe with my glasses, coats and purses. I play it safe with almost everything I wear!

8. Just as I finally made a commitment to glasses that express my personality, I believe I will eventually commit to clothing that better expresses my personality.  Right now, however, even if the whole of Macy’s were my closet each morning, I would still find it difficult to get dressed each day. It’s not only about finding my size–it’s about finding my style.

9. Tights are a great way to take a risk.

10.  It’s a bad idea to choose my clothing based on a bra that I’m determined to wear even though it isn’t right for me just because I haven’t done laundry and the bra is the only one that matches my last pair of clean underwear.

11. Bras matter.

12. Finding tops is still a nightmare. If you know of any great tops in ivory or colors that will go with brown and camel, please share! As you know, I’m giving up black because of my glasses, and sadly, I’m a little too chubby for my own classic white shirts right now. It’s only when I can’t wear something so essential that I realize how much I have come to depend on it.

13. I have a dearth of accessories.

14. Even if I had a million accessories, I could still walk out the door under-accessorized because I couldn’t make up my mind what to wear or how to wear it (especially scarves). (See my Macy’s point in #8 above.)

15. I want a purple cardigan. Maybe this one, but the reviews say it pills. I also want a purple coat, despite what I wrote in #6.

16. It’s okay to be insecure about what I’m wearing as long as I don’t let it stop me. I discovered this last September at the first fashion show I ever attended during a Fashion Week. It was a minor event at the top of a hotel for several designers whose products are made in New York City. There really was a girl in the bathroom wearing a red feather skirt.

I will never wear a feather skirt outside the house. I was proud to be wearing my basic faux wrap dress, but I felt positively matronly next to some of the other attendees. I re-discovered the principle of forging ahead through insecurity when I ventured into Bergdorf’s in November to return a purse I’d cockily purchased online. Any smugness I’d felt about being able to afford a purse on sale through their website was long gone by the time I finished my return, but that didn’t stop me from inspecting the bras in their lingerie department before I left. Guess what? They sell Fauve. Some of my smugness has returned just by writing that.

17. I am not alone. I met the amazing Sweets from SweetNothingsNYC for coffee the night before Thanksgiving. Afterwards, we visited the Wolford store together. When I saw this gorgeous dress (in red), I laughed and said to Sweets, “If I had worn this dress into Bergdorf’s, the salespeople would have had an entirely different attitude towards me.”

Sweets looks amazing and carries herself regally, so I wasn’t sure she would be able to relate, but she totally understood because she’d had a similar experience. What a warm feeling to be able to share my internal struggles with someone else who understands. So often we think we’re the only ones, but we’re not. I hope that this blog and others like it are helping you to feel understood, too.

18. I can learn from you. I have to admit that when Elizabeth joined the OOTD challenge, I was pretty intimidated. Have you seen the effortlessly chic looks she put together? However, I gathered my courage and forged ahead (see #17 above), and now I’m using her for inspiration.

I also took a lesson from Tina’s comment on my navy dress and jeans combo last week. Something that seemed so obvious to someone else wasn’t obvious at all to me, but take a look at the before and after that resulted from her suggestions. (Yay new Navy tights!)

I have more ideas brewing on how we can learn from each other that I want to share with you once I’ve thought them through and have finished discussing them with Tina, Leah and others. Some of you made some great suggestions in the reader survey last July that I’m hoping to find a way to implement.

19. I like the way I look. After seeing so many photos of myself, including all the rejects that never made it to the OOTD Challenge Board, I’m pretty tired of looking at myself, but it’s a relief to be able to say that I like myself. I was concerned that this project would lead to endless self criticism, but it didn’t. I sometimes winced at my back flab, double chin and shiny complexion, but then I moved on. I really like my hair. And my glasses. And my smile. Oh yeah–and my boobs. I forgot about them, which is pretty amazing considering how prominently they’ve figured into every decision I’ve ever made about what to wear since the tenth grade. All my thinking about how to dress big boobs for the past four years must be paying off.