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Un-Fancy

DAILY OUTFITS

Catch Up Session! 28 Days of Outfit Prompts — Outfits 14-22

02/25/25

Here’s what I know:

The magic is in trying things.

Not for the outcome, but to show yourself you’re the kind of person who will try things.

This month, I’ve been getting dressed by trying out a new outfit prompt each day. (Wanna see all 28 prompts? Grab your copy of my one-page PDF right here.)

It’s less about nailing the outfit — it’s more about that boost of positive energy you get when you show yourself that you’re still here, still showing up, still trying new things.

Even if it means people see you efforting. Even if it means people see you kinda goof it up. Even if it means people see you fall flat on your ever loving face.

I’m convinced that the world needs more try-it energy. So don’t be afraid to show ’em you’re trying.

Okay, soapbox, climbing down now. :)

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 14

Prompt: Wear something borrowed or vintage.

OUTFIT DETAILS

Vintage faux fur jacket

Reformation Clara Cardigan

H&M Baggy Regular Jeans

Adidas Sambas

Amazon Chunky Hoops

DAY 17

Prompt: Pair something slouchy with something structured.

OUTFIT DETAILS

Everlane Cocoon Crew Sweater (I sized up 2 sizes for an oversized fit)

Everlane Men’s Premium Weight Long Sleeve Tee

Reformation Cary Low Rise Jeans

Old Vagabond Boots

Alienina Ruth Bag

Casa Ayllon Necklace

DAY 18

Prompt: Grab a piece that you’re not sure how to style. Sandwich it between two familiar, well-loved pieces.

OUTFIT DETAILS

Old Zara Jacket | Similar: ASOS Jacket

Aritzia Homestretch Tee

Reformation Cary Low Rise Jeans

Old Nike Cap

New Balance 530s

DAY 19

Prompt: Channel a character from a book/show that you’re *currently* reading/watching.

OUTFIT DETAILS

Old Madewell Denim Jacket | Similar: Sezane Will Jacket & Reformation Archer Jacket

Reformation Cary Low Rise Jeans

Reformation Cashmere Boyfriend Sweater

Birkenstock Soft Footbed Bostons

Madewell Canvas Cap

Target Hoops

DAY 22

Prompt: Domino dressing: Start with one thing you wore yesterday and build your fit from there.

OUTFIT DETAILS

Aritzia Mega Baggy Foldover Jogger

Aritzia Mega Raglan Hoodie

Aritzia Scrunch Ankle Socks

Amazon Silver Claw Clip

• • •

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. <3

 

2 Comments

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Comments

  1. Jen says

    February 26, 2025 at 10:54 am

    Your statement about the importance of showing yourself that you are the kind of person who will try things really resonates, Caroline.
    I am having so much fun with these prompts; they have become one of many ways I am making and honoring commitments to myself to be healthy, joyful, creative, and grounded as I move through these challenging times.
    Thank you! 💖

    Also, P.S. Nice touch with the Glimore Girls track on that post! It made me smile.

    Reply
  2. Amy says

    February 26, 2025 at 1:56 pm

    This has been such a fun challenge for me! I’ve been able to reimagine the clothes I have already without getting that fashion FOMO. Today I put on a regular fit button down and straight leg jeans (meh) and swapped out for a massively oversized one and barrel leg jeans. Same components, fresh feeling!

    Reply

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