Wear Your Closet Challenge: Outfits 1–5

I thought I’d kick off 2023 with a brand new style challenge: the Wear Your Closet Challenge! Ya can’t keep me away from them for long, ha. I decided to challenge myself to wear different items every single day for an entire month as a way to figure out what I love to wear, discover any glaring wardrobe holes, and determine if anything needs to leave my wardrobe (and what). I realized I have WAY TOO MANY clothes. They’re seriously taking over; I have piles of clothes all over the bedroom that don’t have a home. I don’t know how this happened!

I originally planned to do this in the fall, but then I decided that I liked fall fashion too much to not do regular outfit posts. January was the next best option, and it worked out even better to do it this month. It always sucks to take outfit photos outside during the winter, and now I’m not going to! Plus, it’s a good challenge to kick off the new year, and I have a ton of winter clothes to wear. I also only have one short weekend trip planned. I might do it again in the summer with summer clothes!

Below are the first five outfits from the Wear Your Closet Challenge along with my thoughts on them! I’m sharing weekly outfit roundups on the blog every Friday in January (with the final outfits and a recap coming February 1st). Follow along on Instagram to see the outfits in real time on Instagram stories. I’m also sharing weekly outfit recap reels on Saturdays.

Two other creators are also wearing their closets this month, so be sure to check out their outfits and thoughts as we take on the challenge together: Rebecca of PhD in Clothes and Molly Wetta (formerly of Librarian Style). Join the fun by tagging us and using hashtag #wearyourcloset2023!

Catch up on the other WYCC outfits:

READ NEXT: Outfit Remixes, Capsule Wardrobes, and Style Challenges


Wear Your Closet Challenge: Outfits 1–5


Outfit 1 • Sunday, January 1st

Wear Your Closet Challenge: January 1, 2023 | cropped sweatshirt with joggers and sneakers | Cotton Cashmere Cat Hair

I personally LOVE it when a new month starts on a Sunday, the first day of the week in my mind. It feels like the perfect fresh start (though it does mean that the 13th falls on a Friday!). It’s even better if a new year starts on a Sunday, as was the case for 2023! We pretty much just hung around the house all day on January 1st and only ventured out later in the evening to play games at my parents’ house while my younger brother was still in town (I have three younger brothers, and one lives in Denver so we don’t see him as often).

On Sunday, I prepped my closet for the challenge by turning all of the hangers of my hanging clothes around so I can easily see what I’ve worn and what I haven’t. I have not figured out a good system for the items that don’t hang just yet. I also pulled out everything I am already planning to sell on Poshmark, and I added all of the items I’ve purchased into Stylebook. I went live on Instagram to share my pre-challenge thoughts and plan. It was terrifying but I’m glad I got over that fear!

The first outfit featured four items I still love: my pink velvet baseball cap (purchased via Poshmark), pink cropped sweatshirt, dappled grey joggers, and burgundy sneakers. The joggers were purchased prior to my pandemic weight gain, so they feel a little snug around the midsection and aren’t quite as comfortable anymore. I wore the baseball cap outside for a couple of minutes in a hailstorm and some of the hailstones water stained it. No idea how I’m going to attempt to get rid of those; any ideas for getting water stains out of crushed velvet?

OUTFIT DETAILS

Aliya Wanek sweatshirt / old; similar by Adidas or Nordstrom
Zella joggers / exact (limited sizes) or similar
Allbirds sneakers / exact style (also available from Nordstrom)
Madewell hat / old; similar from Amazon or Shopbop


Outfit 2 • Monday, January 2nd

Wear Your Closet Challenge: January 2, 2023 | cropped top with joggers and slippers | Cotton Cashmere Cat Hair

Day two (Monday) was equally not exciting. Buckle up, because probably 80% of my outfits are going to be not exciting LOL. Though I will say I haven’t put this much effort into my at-home outfits in a while, which is not really saying a lot because these 3-piece outfits aren’t taking a whole lot of effort. 😆 I have basically been alternating between a few sweaters/sweatshirts and sweatpants for what feels like months now.

Korri and I both had the day off of work. We just stayed home all day, and I spent a lot of time on the couch finishing a library book that was due back on Tuesday. I honestly can’t remember what else we did, haha. It was a nice lazy day!

As far as the outfit goes, these joggers are one of my least favorite pairs. They’re soft, and I love the pockets, but they’re a bit long on me and also now snug around the waist. I absolutely love the style of the tee, but the color has been trickier for me to style than I had anticipated. I wear the bone color much more often. I realized that I love cropped tops like this one; they’re the perfect length because they hit at the top of my hips and don’t require a tuck. I need all my tops to be this length!

The slippers are OLD! Pretty sure I bought them in 2008 when I went to Cabela’s with college friends (we got a photo on Santa’s lap, lol). I’ve been debating donating them for so long but they’re still in good shape overall. The fluff on the interior is definitely squished down now. I might turn them into my garage/outdoor slippers. Just haven’t done it yet for whatever reason…

OUTFIT DETAILS

MATE the Label top / exact or similar by Everlane
Amour Vert joggers / old; similar or similar from Nordstrom Rack
Cabela's slippers / old; similar by Minnetonka via Zappos, Nordstrom, or Nordstrom Rack


Outfit 3 • Tuesday, January 3rd

Wear Your Closet Challenge: January 3, 2023 | boxy cashmere sweater with skinny jeans, velvet ankle boots, and wool baseball cap | Cotton Cashmere Cat Hair

Tuesday was supposed to be my one day working in the office this week, but I went to bed the night before with an upset tummy and woke up with a headache and lingering upset tummy, so I took a sick day. Pretty sure I just ate something that disagreed with me (like one of our expired bagged salads, lol). I slept for half of the day and felt better enough to get dressed (in hard pants!) to go out to dinner to celebrate Korri’s mom’s birthday.

Korri thought I looked dressed up lol. I guess because of the velvet ankle boots? I admit that they were a random pick for this outfit, but I went for it because the ground was dry and there was no precipitation. I still adore this sweater and wear it constantly. It’s the perfect shape, and I don’t even hate the dropped shoulders. These jeans are still a favorite but are feeling more snug than usual, though that could be because I had just washed them. I wear this baseball cap all the time in the fall/winter/spring—the wool texture is fun!

OUTFIT DETAILS

Everlane sweater / old; similar or similar by Gap
Madewell jeans / old; similar from Saks Off 5th or Everlane
Earth boots c/o / old; similar by Bella Vita or Target (last seen here)
Madewell hat / old; similar from Saks Off 5th or Nordstrom


Outfit 4 • Wednesday, January 4th

Wear Your Closet Challenge: January 4, 2023 | sweater with sweatpants, no-show socks, and cashmere beanie | Cotton Cashmere Cat Hair

On Wednesday, I worked from home and then went to my parents’ house to hang out before my brother from Denver and his cat flew home. I went digging through a storage box in my closet and found these sweatpants. I had forgotten how lovely they are! They shrunk in the wash and fit quite slim around the legs now, but they remained roomy around the waist and hips. They’re just a touch long, but I still love. They’re so cozy and perfect for winter! I wish they were still available to buy but definitely check for them on Poshmark (Naadam fleece sweatpant).

My brother from Denver so generously gave me this sweater this past Christmas! I had to wear it before he left. It’s made with “extra-soft yarn” and I can definitely attest to the softness. I am not 100% sure why I put my socks on for the photo, but here we are. I love these socks and wish Smartwool still made this particular style! They’ve since replaced them. And this cashmere beanie is my favorite of all of my beanies; it’s so soft. Definitely planning to buy another color or two!

OUTFIT DETAILS

J.Crew Factory sweater / exact
Naadam sweatpants / old; similar from Amazon
Smartwool socks / old; similar from Zappos or Backcountry
Naadam hat / exact


Outfit 5 • Thursday, January 5th

Wear Your Closet Challenge: January 5, 2023 | flannel shirt with joggers and slippers | Cotton Cashmere Cat Hair

Thursday was another work from home day, and I stayed home in the evening. I wanted to wear one of my pairs of Vuori joggers (I own three); I definitely wear my navy pair the most of the three. This sky blue color is a little trickier to style. I thought a blue flannel shirt would look good, but now I’m second guessing it lol. Oh well, at least you’re the only ones that saw this outfit!

I absolutely love my pairs of Vuori joggers and am always tempted to buy more, but three pairs is more than enough already especially when you consider all of the other loungewear I own. I also still like this flannel shirt. It’s an old one from Uniqlo and features a lighter weight compared to some of my other flannels. I love the blue plaid! The slippers are my default when I’m home; I’m almost always in one of my pairs of Ugg slippers. My navy pair didn’t coordinate that well with the other blues in this outfit though, lol.

TOTAL NUMBER OF UNIQUE ITEMS WORN THIS WEEK: 18 (15 not including socks or slippers)

OUTFIT DETAILS

Uniqlo shirt / old; similar from Amazon
Vuori joggers / exact style
Ugg slippers / old; similar from Zappos