Okay! It’s time for a catch up!
This month, I’ve been getting dressed using a new outfit prompt each day.
(Wanna see all 28 prompts? Grab your copy of my one-page PDF right here.)
At first, I found myself really resistant to following the prompts.
But I did it anyway. And now — 18 days in — I’m pretty stunned by the results.
I’ve been falling in love with pieces I haven’t worn in a long time.
I’ve been confidently styling pieces I haven’t been sure how to wear. (Well, confidently-ish. :))
I’ve been feeling that wardrobe-nirvana feeling.
In short, the creative juices are flowing and I’m somehow happier with my closet/outfits than I have been in a while.
AND! I feel like the outfits are coming forth from me — not from a photo on the internet. Which, don’t get me wrong, is a great place to find inspiration. I mean, prompt #10 is all about internet inspo.
But the prompts have shifted my focus from looking at what others are wearing to looking inside my own closet. And that’s been pretty cool.
So, what started with some resistance, is now turning into something special. Jump in with me if you want! It’s never too late. :)
Here are the recent prompts + outfits:
P.S. If you’re reading this via email, and the images are looking a little funny, it’s because they are actually videos. Click ’em and it’ll take you straight to the blog where you can watch.
P.P.S. I’m taking weekends off of posting these fits to Instagram (mental health, bless), so that’s why the days jump sometimes.
DAY 7
Prompt: Try tonal dressing. Wear different shades of the same color throughout your fit.
OUTFIT DETAILS
Old Nike Cap
DAY 10
Prompt: Look at your 5 most recently saved outfit ideas on IG or Pinterest. Pick one to emulate.
OUTFIT DETAILS
Aritzia Low Rise Effortless Trousers
Lululemon Always Effortless Windbreaker
Aritzia Black Homestretch Long Sleeve
JEWELRY
DAY 11
Prompt: Wear a spring piece with your winter outfit (or vice versa).
OUTFIT DETAILS
Abercrombie Low Rise Baggy Jeans
Birkenstock Soft Footbed Bostons
Old Madewell Denim Jacket | Similar: Sezane Will Jacket & Reformation Archer Jacket
JEWELRY
DAY 12
Prompt: Channel a favorite era.
OUTFIT DETAILS
70s
Reformation Cary Low Rise Jeans
Old Madewell Denim Jacket | Similar: Sezane Will Jacket & Reformation Archer Jacket
Vintage Boots
Old Reformation Sunglasses | Similar: Coach Signature Pink Sunglasses
y2k
Aritzia Homestretch Crop Long Sleeve
Old Puffer Jacket | Similar: ASOS Quilted Jacket
Old Polene Paris Umi Bag | Similar: Madewell Sculptural Buckle Shoulder Bag
DAY 13
Prompt: Is there a color you shy away from? Wear it sandwiched between two colors (or neutrals) you love to wear.
OUTFIT DETAILS
Old Nike Hat
Everlane Men’s Premium Weight Long Sleeve Tee
Old Splits 59 Track Pants | Similar: Daydreamer Track Pants
Liffner Tulip Tote (mine is an old color)
JEWELRY
James Avery Delicate Chain (wearing 18 in)
• • •
There you have it! I’ll keep sharing daily prompts + outfits on Instagram and catch-ups here on the blog.
Thanks for reading Unfancy today. It means so much to me that you’re here. Take good care of yourself today.
This is the best challenge ever! It’s really inspiring me to come up with new outfits I love :)
Hi Carolyn,
I’ve tried several times to get the 28 Days file but I never get the email. The first few times I tried I didn’t even get a response when I clicked the link on your website. I tried again yesterday and got a notice that the email had been sent.
No such luck, not in inbox or junk. Not sure what the issue is.
Help :)
Hi Betty! Oh no! I’ll look into it, and in the meantime, I’ll manually send a copy to you. :)
My experiences with these prompts are similar to yours, Caroline. I am using 2025 to pause my clothes buying *and* my decluttering, challenging myself to wear everything I have, including pieces I may ultimately give away, to see if I can style them/wear them/enjoy them/better integrate them into my wardrobe. Your prompts are helping me to get creative with how I do that, and it’s so fun! My appreciation for all of my clothes is growing, and I haven’t yet seen an outfit or piece I like on someone else that I can’t recreate/repurpose from what I already own. How affirming!