A Simple Style Challenge to Reimagine the Clothes You Own

Fashion

Jan 17

Happy Saturday! Today, I’m introducing a style challenge that I was actually going to start the challenge today, but I’ve decided to wait until Monday…just makes more sense to do Monday - Friday. I’m sharing the challenge for each day below and I think it’s going to be so much fun! Each day next week, I’ll be sharing a picture of what I’m wearing for the challenge. I’ll talk about why it works and why I love it. Then….if you like you can hop over to my Substack where I’ll go deeper into the whole thought process and share other options I thought about as I was getting dressed. I’ll also post on my Instagram Subscription page. I hope you’ll join me and maybe even post a picture of what you wore! This challenge is all about thinking a little out of the box and wearing what’s already in your closet…familiar pieces styled in different ways!

Read through the daily challenges below and keep scrolling for some inspiration that may help spark your imagination! I am constantly snapping screenshots on my phone when I see an outfit (or decor or food) that I like so that I can reference them later. This helps me sometimes when I feel stuck or need an idea! I don’t always like the whole outfit necessarily, although sometimes I do…normally it’s just one element that I really like and can incorporate into my look! I’m also including a few recent pictures of me wearing outfits that I really like…and one in my messy closet that shows my creative process sometimes!

I hope you’ll join me in this challenge!

1. The Unexpected Pairing

Wear two pieces together that you’ve never paired before, even if they live in the same closet.

The Challenge - Choose two items you love but have never worn together. Let them surprise you.

2. The One-Piece Anchor

Start with one piece you adore…a coat, jacket, scarf, bag, or pair of shoes and build the outfit around it.

The Challenge - Let one beloved piece lead the way today.

3. Old Favorite, New Mood

Take something you’ve owned for years and wear it in a slightly different way…casual instead of dressed up, or vice versa.

The Challenge - Revisit an old favorite and give it a new mood.

4. Color Where You Least Expect It

Add color somewhere small but intentional…gloves, lipstick, jewelry, a bag, or shoes.

The Challenge - Introduce color where you normally wouldn’t…just enough to change the feeling.

5. Elegantly Undone

Wear something with presence, but keep the rest relaxed - simple hair, minimal makeup.

The Challenge - Choose one expressive piece and let everything else stay effortless - a long strand of pearls, a black leather jacket…whatever you feel is elegant but doesn’t try too hard!