I Spent 75 Days Styling Outfits With Pieces I Already Owned—Here’s What I Learned


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​At the beginning of January, I was scrolling through social when I stumbled upon the #75HardStyleChallenge. I’m not usually one for New Year’s resolutions, but as someone who had recently fallen into the style end of TikTok, I was definitely intrigued. Based on the fitness challenge of a similar name, the #75HardStyleChallenge is the brainchild of fashion creator Mandy Lee (aka @oldloserinbrooklyn): it encourages you to dress with intention, avoid new purchases, shop your closet, and document your outfits for 75 days to explore your personal style.

I’ve always been interested in fashion, but between Chicago winters and my work-from-home wardrobe, I’ve been in a small style rut. During the pandemic, I got rid of a lot of my corporate, office-y clothing that no longer served my remote work setup. And although both my style and my body transitioned in the past few years as I moved into my late twenties, my wardrobe didn’t necessarily come along for the ride. I wanted to push myself to use the 75 Hard Style Challenge. Here’s how it went.

What Is the 75 Hard Style Challenge?

The 75 Hard Style Challenge is a testament to what you already own in your wardrobe. The “rules” include getting dressed every day for 75 days (no matter what you’re doing that day), documenting your daily outfits, and not buying anything new. By shopping your own closet, the goal is getting creative with how you style pieces you already own while simultaneously figuring out a bit more about your personal style.

What I Learned From the 75 Hard Style Challenge

From January through March, I got dressed each day as if I were leaving the house, even if I was working from home. I reorganized my closet, tried new looks, and documented everything via Instagram Stories to create a lookbook to reflect on after the challenge was over. The results were better than I could have ever expected and completely changed how I get dressed each day. Here’s what I learned throughout the course of the 75 days.

I’m more intentional with my time

One thing I always underestimate: how long it takes to get ready. In hindsight, I should have tracked how many hours I spent thinking through my fashion choices over the past 75 days, but I think I added an additional 20 to 30 minutes to my morning routine. And to be clear, I’m OK with that! Experimentation takes time and intention to produce the best results. While it’s a great feeling when your visions work out on the first try, more often than not, something doesn’t fit right or those shoes don’t match or other accessories work better. Giving myself more time to play helps me make sure I’m happy with my final look.

I ask more questions

I mentioned that experimentation takes time—some of that time includes physically trying things on, but most of it is spent thinking through your wardrobe with intention. As I get dressed every day, I ask myself:

  1. What pieces haven’t I worn in a while? I tend to fixate on certain garments. This challenge pushed me to consider what I’ve been neglecting at the back of my closet. Whatever doesn’t fit anymore or no longer suits my style goes in the donation bin.
  2. Will I wear this in public? I’ve spent the better part of the last four years in cozy pajama shorts, sweatpants, leggings, joggers—you name it. Half the time it’s business on the top with a work-appropriate shirt and a party on the bottom with the most comfortable pants I can find. The #75HardStyleChallenge prompted me to get dressed from head to toe (with shoes and all) every day and make sure my outfit is appropriate for public consumption.
  3. How else can I style a piece? Fashion creators like Rachel Spencer and Heather Hurst have inspired me to rethink the way I wear my garments and utilize accessories to transform a look. I’ll try adding layers, wearing something backward, matching different colors, or changing up my jewelry to take my outfit to a different level.
  4. Does this match my personal style? Stylist Allison Bornstein encourages people to describe their wardrobe in three words—classic, bohemian, maximalist, minimalist, etc. These three words aren’t designed to fit you in a box, but rather give you a loose roadmap to looks that you like and feel comfortable in. My descriptors are still a work in progress, but if my outfit doesn’t fit into one of the three categories I’ve selected, I’ll add a layer or accessory that makes the look more “me.”
  5. How do I feel in this outfit? This question goes two ways: physical and emotional. Clothing should never be physically uncomfortable, but it’s good to step outside the metaphorical comfort zone. Even if an outfit looks off, I’ll often wear it for the day anyway. Sometimes a look doesn’t photograph well but I like it in real life; sometimes I just needed a different pair of shoes. Taking time to ponder the details helps me pinpoint what I don’t like about it and what I’d do differently next time.

I know more about what works and what doesn’t

It’s easy to scroll through Pinterest, Instagram, TikTok, etc. and see other people embracing the latest trends or rocking a specific silhouette, but that doesn’t mean that everything will look good on my body type (or that it fits my personal style). After 75 days of experimentation, examination, and critique, I have a much better sense of what styles make me feel the most comfortable—literally and figuratively. Barrel jeans will likely do nothing for my shorter frame, drop shoulder seams make me look top-heavy, and capris are just not for me. Figuring out what works and what doesn’t has helped curb my consumption of clothing that doesn’t work for me, strategically plan new purchases, and renew my sense of confidence to wear whatever I want however I want to.

What started as a fun challenge quickly became a deep journey into my sense of style that transformed my daily routine. 75 days later, I feel better about my wardrobe, my consumption habits, my spending, and myself. If you’re struggling with your wardrobe or want to reset for a new season, I truly recommend giving the #75HardStyleChallenge a try—it’s never too late to start exploring your style.