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The 75 Hard Style Challenge: Week 8

Week 8 of the 75 Hard Style Challenge was one for the books! This week brought a whirlwind of travel, girl time, and a much-needed change of scenery as I headed to New York City with my sister and cousin…

The 75 Hard Style Challenge: Week 8

Week 8 of the 75 Hard Style Challenge was one for the books! This week brought a whirlwind of travel, girl time, and a much-needed change of scenery as I headed to New York City with my sister and cousin. There’s something about being in a new city—especially one as vibrant as NYC—that makes you see your wardrobe (and yourself) in a whole new light. From airport outfits to dinner looks, and from thrift store adventures to cozy work-from-home days, this week was all about versatility, comfort, and celebrating the little moments that make style fun.

The 75 Hard Style Challenge: Week 8

Coming home after a trip always feels a bit like hitting the reset button. I found myself appreciating my favorite pieces even more, and realizing just how much my style has evolved since starting this challenge. Whether I was layering up for chilly city nights or keeping it casual for errands and work, I felt more confident and intentional with every outfit. Here’s how week 8 unfolded!

Weekly Reflections

This week was a reminder of how much joy and confidence can come from getting dressed with intention, especially when you’re out of your usual routine. Traveling to NYC with my sister and cousin was not only a much-needed break, but also a chance to put my wardrobe to the test in a totally different environment. I loved seeing how my favorite thrifted pieces—like my red wool coat and faux leather skirt—fit right in with the city’s energy, and it was so fun to get compliments on items that were true secondhand treasures.

I also realized just how important comfort and versatility are to me, especially when traveling. My sweat sets and wool coats were perfect for the plane and chilly city nights, while my go-to jeans and sweaters made it easy to transition from exploring to relaxing. Coming home, I found myself craving simplicity and ease—opting for casual, no-makeup days and appreciating the comfort of my favorite basics. This week reinforced that style isn’t about having something new for every occasion, but about making what you have work for your real life, wherever you are.

Daily Outfit Diary

2/19: NYC Arrival & Two Outfits

We’re in New York! I was so excited to kick off the trip with my sister and cousin. For the plane ride, I wore my favorite sweat set and my new brown wool coat—perfect for traveling and staying cozy. I’m convinced sweat sets are the way to go for flights.

For exploring and dinner in the city, I changed into an all-black look with my favorite sequin pants, a black top, and my new red wool coat. I got so many compliments on the coat, and both wool coats kept me perfectly warm all day and night.

2/20: Thrifting in NYC & Dinner

Today was all about thrifting! I wore my thrifted cashmere sweater, lightwash Levi Ribcage jeans, and my brown wool coat. The weather was unusually warm, and this outfit was just right for walking the city and hopping on and off the subway. I found a couple of cute tops at Goodwill but passed on a fur coat with sleeves that were too short. For dinner, I changed into my new thrifted faux leather skirt, a thrifted long-sleeve silk top, and my red coat—super comfortable and warm for a chilly NYC night.

2/21: Flea Market Day

The 75 Hard Style Challenge: Week 8
Purse: Saint Laurent – Scarf: thrifted – Coat: thrifted – Belt: Gucci – Sweater: thrifted – Jeans: H&MBoots: Nordstrom Rack

Saturday meant flea market day! I wore my thrifted cotton navy sweater, H&M inky jeans, and my red coat. We shopped all day, but I didn’t find anything for myself. I did pick up some fun things in Chinatown for my husband and kids, so the day was still a win. After all that walking, I decided to stay in for the night and save my planned dinner outfit for a date night at home.

2/22: Travel Home

The 75 Hard Style Challenge: Week 8
Sweater: thrifted – Belt: AmazonJeans: H&MSneakers: Target

Heading home today! I spent the morning at the airport catching up on work. I had planned to wear my sweat set again, but since I wore it longer than expected on Thursday, I switched to jeans and a sweater for the flight. This was actually the outfit I meant to change into after landing on Thursday, but the room wasn’t ready, so it got its moment today. As soon as I got home, I changed into pajamas and relaxed.

2/23: Dishwasher Shopping

The 75 Hard Style Challenge: Week 8
Purse: CoachVest: Marshalls – Tee: thrifted – Belt: Target – Jeans: Levi RibcageSneakers: Target

Back to reality! The hubby and I went dishwasher shopping since ours finally gave out. It was cooler than I expected, so I wore a long-sleeve tee, a vest, and my favorite Levi ribcage jeans. Sneakers were a must—my feet were still tired from all the NYC walking. The outfit ended up being perfect as it warmed up later in the day.

2/24: Casual Work-from-Home Day

The 75 Hard Style Challenge: Week 8
Sweater: TargetJeans: Levi Low Pro – Clogs: Walmart

Today was super casual—just working from home and a quick grocery run. I wore a cropped sweater, Levi Low Pro jeans, and clogs for errands. No makeup today; I wanted to give my skin a break after wearing it all week in NYC. Honestly, I felt a little lazy and didn’t put much effort into my outfit, but sometimes that’s exactly what you need.

2/25: Tax Meeting & Home Day

The 75 Hard Style Challenge: Week 8
Purse: CoachSweater Tee: TJ Maxx – Jeans: H&MBoots: Marshalls

Another work-from-home day, but a busy one! We had our tax meeting with the CPA, and I was a little anxious about it. I went with simple H&M jeans and a knit top to feel put together. If I was going out, I would have added boots and my brown Coach purse. The new dishwasher was also delivered today, so even though I was home, it felt like a full day.

What I’m Learning

This week really drove home the importance of versatility and comfort in my wardrobe—especially when traveling. I realized that having a few go-to pieces, like my sweat set and wool coats, makes packing and getting dressed so much easier. I also learned that it’s okay to repeat outfits or lean on favorites, especially when they make me feel confident and comfortable in new environments.

I’m also noticing how much my style has evolved since starting this challenge. I’m reaching for thrifted pieces that feel special and unique, and I’m more willing to pass on things that don’t fit perfectly or don’t add real value to my closet. Coming home after a busy trip, I appreciated the simplicity of casual, no-fuss outfits and the comfort of my everyday basics. Most of all, I’m learning that style is about feeling good in what you wear—whether you’re out exploring a new city or just working from home.

My Current Wardrobe “Needs” List

Even with all the shopping and thrifting in NYC, my wardrobe needs list is holding steady. I didn’t find anything this week that truly felt like a must-have or filled a gap in my closet, so my wish list remains the same.

The 75 Hard Style Challenge: Week 7 - Wish List

I’m proud that I didn’t settle for anything less than perfect, even with all the temptation of new stores and city shopping. This challenge has taught me to be patient and intentional, and I know the right pieces will come along when the time is right.

Wins, Challenges, and Surprises

Wins:

  • Packed and wore outfits that were both comfortable and stylish for travel and city adventures.
  • Got lots of compliments on my thrifted red wool coat—proof that secondhand finds can be true statement pieces.
  • Didn’t settle for anything less than perfect while thrifting in NYC, even with the temptation of new stores and unique pieces.
  • Came home and embraced simple, no-fuss outfits that made the transition back to routine easier.

Challenges:

  • NYC shopping was fun but a little disappointing since I didn’t find any wardrobe staples to cross off my list.
  • Felt a bit lazy and less motivated to dress up after returning home—sometimes the post-trip slump is real.
  • Balancing the excitement of travel with the reality of everyday life and responsibilities (like tax meetings and appliance shopping).

Surprises:

  • Realized how much I rely on a few favorite pieces for both comfort and confidence, especially when traveling.
  • Appreciated the value of girl time and how it can recharge my mood and outlook, even if it doesn’t result in new wardrobe additions.
  • Noticed that my style is becoming more about how I feel in my clothes than about chasing trends or newness.

Looking Ahead

With just a couple weeks left in the 75 Hard Style Challenge, I’m feeling both reflective and motivated to finish strong. I want to keep focusing on comfort, versatility, and only adding pieces to my wardrobe that truly feel right. As I settle back into my routine after NYC, I’m excited to see how my style continues to evolve and how these new habits stick once the challenge is over.

I’m also looking forward to a little more spring weather, experimenting with lighter layers, and maybe finding that perfect piece I’ve been holding out for. Most of all, I want to keep enjoying the process—celebrating the small wins, learning from the challenges, and staying true to what makes me feel my best every day.

Style Challenge Series
Operation Organization Operation Organization - Jennifermeyering.com
The 75 Hard Style Challenge The 75 Hard Style Challenge
The 75 Hard Style Challenge: Week 1 The 75 Hard Style Challenge: Week 1
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The 75 Hard Style Challenge: Week 7 The 75 Hard Style Challenge: Week 7
The 75 Hard Style Challenge: Week 8 The 75 Hard Style Challenge: Week 8

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