I am halfway through my wardrobe challenge! And, I have to admit, I’m getting kind of sick of my own clothes. I am honestly finding it hard to motivate myself to Keep. Wearing. Everything. It’s hard to put on that nice blouse, when all I want to do is return to my regular tees. It’s hard to wear a sweater on a day when I would usually just put on my yoga clothes and call it good. Getting out of my own comfort zone has been truly challenging. Which is something I wouldn’t have predicted prior to this challenge. But, I only have 18 more outfits to wear before I’m done, so I’m going to keep doing this! And, again, I continue to learn things about myself from this challenge:

  1. I didn’t know that I didn’t know. Prior to wearing every piece of clothing that I own, I felt pretty confident that I “knew” my style. That I knew what made me look good, and what made me feel good. But doing this challenge revealed that I really didn’t know! I am much more in tune to what looks flattering on me, what makes me feel good, and what I really want to wear and present to the world after this whole process.
  2. I couldn’t take it anymore. My jeans seriously sucked. So, right after outfit 11 (which I didn’t even get a picture of, because it looked just sad!) I told my husband that I was fed up. I bought four new pairs of pants. I threw away four pairs of my old pants, and I am so, SO happy that I did! I feel sexy in these new pants, and confident. It’s a good feeling.
  3. My attitude towards my clothes is the single most important thing. I’ve discovered that the key to cutting down on my clothing clutter is to listen to my own feelings regarding my clothing. I’ve learned that when I feel discouraged, or disappointed, or unhappy with my clothing, then it’s just not worth keeping it around. When I look at my randomized list of outfits, and I find myself feeling bummed about having to wear something, then I know that it’s time to let that article of clothing go. Even if it’s something that I have been complimented on. If I’m constantly tugging at it, or fidgeting, or just feeling strange about, then it needs to go. Period.
  4. I own too much stuff. When I first told my friends about this challenge, I mentioned that I had pared down my wardrobe to 38 shirts. My girlfriends couldn’t believe it. “Thirty-eight shirts? Thirty-eight??” I had been so proud of my wardrobe reduction up until that moment. I mean, doesn’t everyone have a closet so packed and disorganized that Lorelei Gilmore would shed a tear of pride? The answer, of course, is no. And nobody needs a closet like that, either (I mean, in seven seasons Lorelei and Rory never actually repeat an outfit. Real human beings just don’t need that much fabric in their lives!). Prior to starting this, I thought getting down to 25 tops would be impossible. Now, I can see it happening. Easily. Hell, I could probably do more! But, the really big news about this realization is that I’ve started turning my now-discerning eye to the rest of my house. How much stuff do I really, truly, genuinely need? How much do I have? How much do I use? How can I bridge the mathematical divides between my answers to those questions? All of this is to say that you should all come to my yard sales this spring! They’ll be LOADED!

Day 11: I didn’t get a picture of this outfit. But it wasn’t good. Old jeans, completely ripped through on the hem. A plain white t-shirt so old and threadbare you could see through it. (Seriously, girlfriends, why did you guys just let me walk around with all my business on display for so long?? Couldn’t one of you have mentioned that you could see everything through my crummy old shirts??) They both went in the trash. I wouldn’t want to donate things that old and beaten up.


Day 11

Day 12: My grey Goodwill pants continue to rock it (and my pink socks are adorable–you know they are!). But I have realized that I actually own THREE different teal blue, racer back tank tops. This one is by far the least flattering. Boi, bye!

Day 12

Day 13: Oh, the joys of new jeans! These are Tommy Hilfiger “Pull-On Skinny Jeans.” Do you know what that means? It means they are basically fancy elastic waist pants! No zippers or buttons, but still made out of denim. I’m in love. They’re a *touch* too long, but I adore them with a little cuff at the bottom, so I don’t think I’m going to even hem them. So cute. Keep.

Day 13

Day 14: Okay, this sweater has me confused. It’s warm, and I really like the styling on the back, but I’m just not sure I feel super confident in it. The pants are flat out far too tight. They’re already gone (replaced by much better things!), but I just can’t decide if I want to keep this sweater. I get compliments on it, but I dunno. Can you guys give me some feedback? What should I do?

Day 14

Day 15: Behold. My new William Rast jeans. Justin Timberlake designs these jeans, and I told my husband that they remind me of what I imagine snuggling with JT might feel like: soft, buttery, flexible, yet completely supportive, and so good for my ass. They’re total “touch me” pants. Even my rough-around-the-edges husband couldn’t stop–ahem–rubbing these jeans. Just paired with my old tee, they were perfection. And, yes, I am totally saying “Ooooh” to my own butt in this picture.

Day 15

Day 16: Don’t let my expression throw you off. This picture was taken at the end of a long day and I was tired. This is my favorite turtleneck, paired with my ankle length black leggings. I really like them both a lot. And these leggings are now my only “non-jean” pants. I think keeping them will add some versatility to my wardrobe. Keep!

Day 16

Day 17: Just in case anyone thought that these photos had been retouched or edited in any way, let this prove to you that they have not. Fresh out of the shower. Wet hair. Shiny, just-washed face. I’m wearing my new pants that are replacing my way too big brown “placeholder” pants. These olive green ones are cozy, but LONG. Definitely going to have to hem these suckers! And my top? I’m never getting rid of it (it says “The Maddie Lous,” and we sold them to raise money for Riley Children’s Hospital in honor of my Riley kid, Maddie. They’re baseball shirts, because her initials are MLB. I thought I was being so clever!). But I think it has to become a paint shirt. It’s just kind of meh on me. Hits me in kind of awkward places.

Day 17

Day 18: I’m sex on a stick and I know it. (This orange tank is my FAVORITE top! And I honestly probably would have never paired them with these grey pants. But, yowza.)

Day 18

Day 19: Black William Rast jeans. Also need to be hemmed, but they’re so freaking soft. And there’s a great story behind this top. I got this hoodie years ago at a store in Montreal, Quebec that specialized in small-production and sample sales from tiny, independent designers. This was a runway sample. The only one like it in the world. It’s long, warm, has a hood AND pockets. I’m never getting rid of it. But I had to pull it up in the back because you guys just need to experience my booty in these new jeans. I mean. Come on.

Day 19

Day 20: Further proof that absolutely NOTHING has been Photoshopped! I took this picture this morning, unshowered, greasy, running out the door to drop my daughter off at preschool. I threw on this beautiful pink hat that my closest neighbor (and closest friend) made for me. Fashionable, AND saved the world from experiencing the horrors of my bed-head. I’m also so happy that I finally found another t-shirt in my closet that doesn’t have stains!

What does everybody think? Did I do a good job picking out my new jeans? Have I gotten rid of something that is just too cute to bear? What should I do with that pale gold sweater?? Let me know! (Seriously. Help a sister out!)

What’s my wardrobe challenge? Check it out here: Dressing Like Cher

Missed my first ten days? Here’s the link!