Two weeks into the 75 Hard Style Challenge, and I’m already noticing how much more intentional I’m being with my wardrobe—and how much I’m learning about what I actually like to wear.
This week was a mix of errands, family outings, and plenty of time spent working from home, but I still made the effort to get dressed with purpose every day. I’m finding new favorites, letting go of pieces that don’t work, and discovering that sometimes the little details (like accessories!) make all the difference.
If you’re curious about what a real week of intentional dressing looks like, here’s my daily outfit diary, what I’m learning, and the surprises that popped up along the way.
Weekly Reflections
Two weeks into the 75 Hard Style Challenge, I’m starting to see some real shifts—not just in my wardrobe, but in how I think about getting dressed each day. I’m noticing patterns in what I reach for, what makes me feel good, and what I’m ready to let go of. This week, I found myself paying more attention to the little details, like accessories (or, honestly, forgetting them!), and realizing how much they can change the feel of an outfit.
I’m also getting more honest about comfort and fit. If something doesn’t feel right—like jeans that ride up or pants that are too soft and lose their shape—I’m not hesitating to add them to the consignment pile. It feels good to let go of pieces that just aren’t working, and it’s making space for the things I truly love.
Another thing I’m learning is that I don’t need a special occasion to wear something fun or bold. My sequin pants, for example, used to feel like a “special event only” piece, but I’ve realized I can style them for everyday and actually enjoy them more. I’m also getting better at sticking to my low-buy goals, only picking up things I really need and using gift cards when I can.
Overall, I’m feeling more confident and less overwhelmed by my closet. I’m still figuring out how I feel about certain styles—like straight leg jeans—but I’m enjoying the process of experimenting and refining my preferences. I’m excited to see how my style continues to evolve as the challenge goes on!
Daily Outfit Diary
1/8 – Dentist, Goodwill, and Favorite Jeans
Had a dentist appointment and made a quick stop at the Goodwill boutique to see if they had anything new on my needs list—left empty-handed this time. I also dropped off three bags of clothes for donation and returned some gloves I bought for my husband. I really liked my outfit today: my favorite jeans (just in a different wash), a soft sweater tee, and a new jacket for the season. The jeans were a bit shorter than I wanted, and I should have chosen different boots, but I liked the casual vibe. I totally forgot to add accessories, which made me realize how much those little details can finish an outfit.
1/9 – Work-from-Home & Jeans That Didn’t Make the Cut
Stayed home and worked today. Instead of defaulting to an outfit set, I put on jeans and a shirt. After a few hours at my desk, I realized I don’t like these pants anymore—they’re too soft, lack structure, and keep riding up. Into the consignment bin they go! Comfort and fit are becoming non-negotiables for me.
1/10 – Family Outing & Rhinestone Pants
Took the kids to monster mini golf and then out to dinner. I loved my outfit, even though I wasn’t quite dressed for the colder weather. I’ve always wanted rhinestone/sequin pants, and when I found these Levi’s in my favorite cut last year, I had to have them. This is only my second time wearing them, but I’m determined to style them more often. I realized you don’t need a special occasion to wear sequins—sparkle can be for any day!
1/11 – Target Run & The “Keep or Purge” Test
Just had a quick run to Target today, then came home to work and write in my new planner. I stuck to my list and only bought what I needed (thanks, low-buy challenge!), and even used a gift card. I loved my outfit: favorite jeans (different wash), a nice sweater, and a trench coat for the cold. I noticed that if I don’t immediately want to change into comfies when I get home, it’s a sign the outfit works. If I do, it’s time to reevaluate those pieces. This was not one of those times.
1/12 – Day Date & Rediscovering Favorites
Returned some pants for my husband and grabbed lunch together—trying to do more day dates while the kids are in school. I worked for a few hours in the morning and really liked my outfit. The pants from H&M are my second favorite after my Levi’s Ribcage: structured, high-rise, wide-leg, and the perfect length for a heel. The cardigan is a longtime favorite that I haven’t worn much, but that’s going to change. Felt put together and well-dressed all day.
1/13 – Dentist, Thrifting, and Straight Leg Jeans
Daughter’s dentist appointment, some lab work, and then thrifting after school drop-off. My outfit was quick and easy—perfect for thrifting, though not something I’d wear for much else. The sweater was soft and comfy, and the jeans (Levi’s, straight leg) are a nice baggy fit. I’m still on the fence about how I look in straight leg jeans, but they’re comfortable and good for sitting at my desk.
1/14 – Simple, Casual, and Styling Straight Leg Jeans
Another simple outfit for a day of working at my computer, with a quick Walmart run for the kids’ shoes. No makeup, casual clothes, and trusty boots for errands. These jeans are labeled wide leg from Old Navy, but they fit more like a straight leg on me. I like them—they’re comfortable and slightly stretchy. I’m noticing I prefer straight leg jeans with a little heel instead of sneakers; it makes the look cleaner and less bunchy at the bottom.
What I’m Learning
This second week of the challenge has really reinforced how much the little things matter when it comes to getting dressed. I’m realizing that accessories, shoes, and even the right outerwear can completely change the vibe of an outfit—and that I’m not always great at remembering those finishing touches! It’s something I want to be more intentional about as the challenge continues.
I’m also learning to listen to my body and my comfort level. If something doesn’t feel good—like jeans that ride up or pants that are too soft and lose their shape—I’m not afraid to let them go. It’s freeing to be honest about what works for me now, instead of holding onto pieces out of habit or guilt.
Another big lesson is that I don’t need a special occasion to wear something I love. My sequin pants, for example, used to feel like a “just for parties” item, but I’ve realized I can style them for everyday and actually enjoy them more. It’s fun to bring a little sparkle into the ordinary.
I’m also noticing that my “needs” list is evolving as I pay more attention to what I reach for and what I wish I had. I’m getting clearer about what would actually add value to my wardrobe, rather than just shopping for the sake of it.
Most importantly, I’m learning that intentional dressing is a process. Some days are hits, some are misses, but every day is a chance to learn more about my style, my preferences, and what makes me feel good.
My Current Wardrobe “Needs” List
As I continue to get dressed with intention and pay attention to what I actually wear (and wish I had), my wardrobe “needs” list is evolving. Instead of shopping on impulse, I’m focusing on filling real gaps—pieces that will help me get more out of what I already own and make my wardrobe feel more complete.
Here’s what’s currently on my list:
I’m still prioritizing thrift and secondhand options whenever possible, and I’m only adding something if it truly fits the bill. The goal is to build a wardrobe that’s versatile, timeless, and genuinely useful for my lifestyle—not just a collection of random pieces.
Wins, Challenges, and Surprises
This week brought a new set of little victories, a few frustrations, and some unexpected discoveries as I kept up with the 75 Hard Style Challenge.
Wins:
- I stuck to getting dressed intentionally every day, even on the days I was just working from home or running errands.
- I let go of jeans and pants that didn’t fit right or weren’t comfortable, making more space for pieces I actually love.
- I wore my sequin pants for a regular family outing and realized I don’t need a special occasion to wear something fun.
- I stuck to my low-buy goals, only buying what I truly needed and even using a gift card for my Target run.
Challenges:
- Remembering to add accessories and finishing touches to my outfits—sometimes I forget, and it really does make a difference.
- Still figuring out how I feel about straight leg jeans and which shoes work best with them.
- Letting go of pieces that used to be favorites but just don’t work for me anymore.
Surprises:
- How much my mood improves when I wear an outfit I love—even if I’m not leaving the house.
- Realizing that comfort and fit are non-negotiable for me now; I’m much quicker to let go of things that don’t feel good.
- How much more confident I feel when I take the time to get dressed with intention, even if it’s just for a simple day at home.
This week has shown me that progress is about the small, consistent choices I make every day. I’m learning to celebrate the wins, face the challenges head-on, and stay open to the surprises that come with experimenting and refining my style.
Looking Ahead
With two weeks down, I’m feeling more motivated than ever to keep going with the 75 Hard Style Challenge. I’m excited to keep experimenting with new outfit combinations, especially as I get more comfortable mixing and matching pieces I might have overlooked before. I want to push myself to try styling some of the items on my “needs” list in new ways, or see if I can find creative substitutes with what I already own.
One of my goals for the next week is to be more intentional about accessories and finishing touches—maybe even set out a few options the night before so I don’t forget in the morning. I also want to keep refining my list of wardrobe wants and needs as I notice what I’m reaching for (or wishing I had) each day.
I know there will still be days when I feel uninspired or tempted to shop, but I’m reminding myself that this challenge is about progress, not perfection. I’m looking forward to seeing what I’ll learn in week three and sharing more of the journey here. If you’re following along or doing your own style challenge, I’d love to hear how it’s going for you—let’s keep each other motivated!
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