The Daily Outfit Diary Experiment

What if one photo a day could help me show up like I want to? Asking questions that matter to you can turn a camera into a personal tool for self-discovery.

Here’s something I nevah-evah-evah thought I’d do: Take pictures of myself every day and appreciate it.

Credit: Death to Stock

As Health magazine’s former diet editor and in my current role (I’m content manager for a telehealth weight care company), I can tell you that even in an era where the average American takes 20 photos a day, of all the weight loss success stories I’ve written or edited, no one’s ever had more than one or two pictures of themselves at their highest weight.

I didn’t, either.

As I started losing weight, people in my support groups encouraged taking photos along the way for motivation. I rarely did it.

If you avoid photos as I did, using selfies as a tool of self-discovery might feel impossible. For many, there’s weight bias and body shame to overcome.

Changing my relationship with the camera

How’d I begin turning this around?

It started with something I wanted to track. I set a goal of building a capsule wardrobe around color. Indyx, a digital wardrobe app, has a feature that tracks the color composition of my wardrobe, how often I wear colors, and even the cost per wear by color.

Indyx also has an outfit tracker that allows you to upload daily selfies. I thought that would be a cool way to track how well I’m reaching my color goals.

Then, while reading Big Dress Energy by fashion psychologist Shakaila Forbes-Bell, this statement in her version of the proximity of clothes to self survey hit deep:

I’m aware of the impression my personal style gives off.

I really wasn’t. Sure, U.S. culture has basic style concepts, like a single-breasted blazer = professional. But that wasn’t my personal style.

Plus, I often felt that my size primarily shaped what people thought of me. No matter what outfit I wore, I thought my weight trumped it.

I wanted to start looking at myself in the mirror differently. Not just to check for things like stray threads, zipped zippers, and aligned buttons, but to look for alignment with who I want to be.

This can be deep work, and some days you gotta get out the door fast. No time for intense style introspection when you’ve got to make your way through Atlanta traffic. So, selfies made sense. Reviewing a group of photos allowed me to see trends more easily than a daily moment in front of the mirror. I also noticed I wasn’t as meh about studying pictures.

I experimented with taking daily photos for three weeks. I set aside time to review the images with a list of questions.

Ask open-ended questions that matter to you

Here’s my list. Some are more practical than others. Some helped me tune in to myself. This set helps me work through how much I never really loved my clothes and how I mentally checked out when it came to getting dressed.

• How do my clothes fit?

• Am I wearing color the way I intend?

• Am I comfortable?

• How do my outfits make me feel?

• What vibe is my outfit giving?

• What do I like about what I’m wearing?

• What do I need to get closer to the person I want to be?

I thought of this three-week experiment as part one of a style selfie diary. My goal’s been to learn from it, change some things, take a break, and when I’m ready, repeat with a different list of questions.

If you try it, ask yourself questions that address what you want to learn or work on. I’d recommend keeping it to three to five questions. I also suggest doing it for a limited time—a week or two, or as you’re comfortable. Check in with yourself.

You don’t have to post these publicly. This exercise is personal. It should feel for you.

The daily outfit diary

Here are pics from my first go at a daily outfit diary. I had fun with some—they started to look too much like lineup photos, and I wanted to build a positive relationship with taking pictures.

I’m happy with how I’m incorporating color. This exercise also helped me see some things I want to work on. (Accessorizing, for one!)

Live Convo!
Using Your Imagination to Discover Your Style and Yourself

with Josh Miller, host of Adorned in Imagination
Tuesday, June 24 at 7pm ET / 4pm PT | Register + calendar reminder

This is going to be a powerful conversation! We’re going to talk about using imagination to define and express our style and ourselves.

Josh Miller is a multi-disciplinary artist whose life’s work is creating a more inclusive world. They’ve been on a journey to uncover their identity and find new forms of self-expression through style, and that journey’s taken Josh around the globe to learn about culture, clothing, adornment, identity, liberation, and transformation. They’ve taken all that and put it into a new video series, Adorned in Imagination. (Link to episode 1 is below.) Join us or catch the recording.

1. To learn more about fashion psychology and how to apply it to support your style, confidence and well-being, pick up Big Dress Energy (hardcover, $28 USD, Bookshop.org) by British fashion psychologist Shakaila Forbes-Bell.

2. I mentioned Indyx above, a digital wardrobe app that’s great for cataloging individual pieces, creating outfits, categorizing by season, and tracking cost, cost-per-wear, usage, and more. Download & use the app for free; get access to more features for $9 USD monthly or $74.99 USD per year. (The Indyx site says Insider pricing is as little as $5 USD a month.) The hurdle of using a digital wardrobe is initially uploading all your pieces. Indyx will send someone to do it for you starting at $295 USD per 100 items. Personal styling is also available for an additional cost. Download Indyx from the App Store or Google Play.

3. I can’t send you off to use pictures as a lens for self-discovery without pairing it with some guaranteed positive vibes. Check out Joy Bombs, a deck of 52 brightly-colored affirmation cards from SoCurious. Normally $22 USD, they’re currently $10.

• None of these are affiliate links.

• I know the world is insane right now and shopping can seem frivolous. Here’s my perspective: small businesses need regular customers more than ever. (It’s all about jobs, families, communities, generational wealth…) Spending money intentionally is one way you can create the world you want to live in. I link to companies owned by marginalized people when I can. If you know any that are related to fashion or self, please turn me on—I’ll share some here.

Thanks for reading re:dressing! If you know someone who would enjoy this, please share!

Re:dressing is a currently free newsletter I publish every other Tuesday.

My goal with re:dressing is to build a community for people who want to grow and feel confident about expressing themselves through style after weight loss and other physical and life changes. Subscribe to stay connected.