The Case for Documenting Your Outfits

Sharing my favorite looks from April, what I regret buying, my big style "aha" moments, and my best tips for taking photos of your looks.

At the start of April, I decided to take a photo of every outfit I wore—not to post, just to see. What would I actually choose on busy mornings? What colors did I keep reaching for? What felt good, and what didn’t? Here is what I learned.

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When I started this journey to rediscover my personal style, I knew I had to do two things. The first was to get rid of any clothes that no longer fit me. I don’t need that stress in my life! The second was to take pictures of my outfits—every single day. And so, I started documenting my outfits in earnest in April.

A big part of what inspired this meticulous documentation has been Anna Newton’s “Everything I Wore This Week” series in The Wardrobe Edit. Reading about what someone wore initially seems rather generic, yet it’s become one of my favorite pieces of content to read online. (It helps that I love Anna’s sense of style, too.) I am nosy! I want to know what you wore to work from home and on a coffee date with a friend!

An outfit photo, however rote it seems, is an intimate portrait of you at any particular moment. I love knowing the what/where/why of an outfit. How did you land on it? What occasion were you dressing for? What was the weather like that day? What shoes did you try on with the outfit before deciding on this particular pair? How were you feeling? How were you hoping to feel after getting dressed? It’s easy to dress for the camera if you know you’re just going to pose for Instagram pics or TikToks. It’s another thing to dress for real life.

My “real life” style is pretty basic and practical—a lot of jeans and t-shirts. There’s nothing wrong with that, but part of this new personal style journey I’m on will be to figure out how I can marry practicality with creativity and self-expression. I love fashion! It takes up much of my brain and my feeds! But I struggle with translating inspiration into reality. How can I jazz up a look without sacrificing comfort and feel totally like myself and have fun with it? This is my goal.

My favorite looks in April, which I get into in detail below!

So without further ado, included in today’s post is:

• my five favorite outfits from April (and my biggest takeaways)

• my best tips for documenting your outfits

• a surprising realization about my “style words”

• something I regret buying!

Let’s get into it.

What I Wore: My 5 Favorite Outfits From April