My Journey to Learn How to Dress Well, Finally

Using the INDYX app to digitize my wardrobe, or not

Dunelair
Crow’s Feet
6 min readJun 13, 2024

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Shirts to photograph for INDYX app. Photo by author.

I lived 81-plus years paying little attention to my appearance.

During my career, I haphazardly tried to dress the part off and on, but I never learned and applied the basic principles of presenting oneself through one’s clothes.

I was always stumped trying to put together a travel capsule for a trip because my garments did not mix well. I occasionally read relevant articles, but I generally resisted following the crowd.

In my retirement, I have mostly worn my uniform of Gloria Vanderbilt jeans from Costco topped with a tee from L.L. Bean. Frankly, I have resisted thinking about changes due to aging.

Like many American women, I have closets full of clothes that do not serve me well. I seldom feel put together, and I have been in denial about how nonfunctional my wardrobe is.

Over the last year, I discarded many items following Marie Kondo’s principle of sparking joy. Although I did not get much pleasure from the process, I thinned out many garments that were not working for me. Nevertheless, my wardrobe remains problematic.

Downloading the INDYX app onto my phone

A few weeks ago, I learned about the INDYX app that you can use to digitize your wardrobe and create multiple “outfits” to help you choose what to wear when you lack inspiration.

A fashionista named Yidi Campbell assembled a team and created this impressive app. Not only does the app work beautifully, but Yidi and her team have produced an eight-week course with several well-written articles to guide new users.

Their articles explain how to use the app, but more importantly, they lead you through a structured thinking process about redefining your approach to shopping and fashion to improve your satisfaction with what you are wearing.

They also aim to raise awareness of today’s advertising practices, which lead to overbuying and attendant harm to the environment. While the app is free to download and use, the company offers styling and other services that you can purchase.

The readings focus on helping you understand your intentions and build knowledge and skills to meet personal goals in managing your wardrobe.

I wanted to avoid becoming burdened with data entry, so I decided to digitize only my clothes that I might wear to book club, going out to lunch, or similar activities. I am not abandoning my jeans and tees, which define my everyday look. My lifestyle is casual, so I do not need fancy party wear.

The eight-week course

As a writer, I appreciate that the articles of the eight-week course are well written. Reading them feels like having enjoyable conversations with knowledgeable advisors.

Their smart guidance begins with four weeks to help you define your style. During the next two weeks, you digitally catalog and evaluate your wardrobe, and in the last two weeks, you “Build Your Roadmap” to achieve your goals.

Early on, I realized that all my life I have resisted learning how to create a wardrobe that serves me well. I was in denial about the skills I needed to devise outfits I enjoy wearing.

I want to take pleasure in what I wear, buy better quality pieces that work well together, and be confident that I am well dressed.

Because of the course, I am paying attention to what people are wearing, and it is a revelation. Women like to feel “put together,” and they make a point of doing it well. And I can learn from them.

On the one hand, I am embarrassed to admit my backwardness in attending to my appearance. Still, I realize there must be many other women who lack skills in navigating today’s aggressive consumer environment to optimize their wardrobe for their lifestyle. Otherwise, there would be no need for INDYX-type apps.

Lessons I learned while creating my inspiration board

Following the course guidance, I clarified my intentions for my wardrobe and used Pinterest to collect images of outfits that appeal to me and are consistent with the words that define my style.

Chief among my insights were these:

(1) Jeans + tee is today’s women’s uniform. This surprised me; this is me. I also learned that I am not the only person who has observed the prominence of a monochrome approach to dressing today.

(2) If we are to be thought well-dressed, it is essential to combine the jeans + tee with a carefully chosen layering piece and accessories to be sure that all elements have the same vibe. The layering piece can be the defining statement of our style, and it can break the monochrome formula.

(3) A corollary here is that hair and nails are fundamentally important.

(4) Another precept is that shoes are far more significant than I had imagined.

(5) Although I fit in wearing my classic jeans and tee, I fell short in polishing and personalizing my look. As I develop my outfits, these are the areas I need to work on.

(6) Although I knew what an influencer is, this experience introduced me to many who work in fashion. I was struck by how alike they are. A few stand out for the quality of their work, but many are copycats.

(7) It is challenging to break from the uniform and express one’s personality when the entire world seems intent on wearing jeans and a tee, or pants and top of the same color. If our personality is to shine, we must personalize the formula.

According to the INDYX team, “Styling is a process of experimentation and critical thinking that makes your closet work better for you.” Do you want to express your personality, or do you want to project a look for some purpose?

I need to become more aware of what others wear and analyze what works and what doesn’t and why.

Digitizing my wardrobe

I jumped right into photographing my tops and bottoms and adding them to the app. Not surprisingly, it quickly became tedious, and I do not live in a major metropolitan area where the INDYX team provides the service. Even if I did live in their service area, I would consider their fee more than I could afford.

So, I decided to bear with it and return to the data loading process. However, in parallel with this activity, I was giving myself a crash course in fashion awareness, and I learned a lot.

Other influencers advised to take a selfie of each outfit as you wear it, and that seemed like a better approach for me.

At this point, my plan is to do this and devise a simple inventory to jog my memory when I feel frustrated trying to decide what to wear to an event.

The third part of my memory jogging gambit is creating better storage arrangements that allow me to visually inspect all items I have in a category.

My conclusion is that the INDYX app is primarily designed for a wealthy person with an extensive wardrobe who can afford to buy the company’s styling services. Nonetheless, it could be helpful for the patient do-it-yourselfer attuned to the app’s approach.

Evaluating my wardrobe

During the sixth week, my assignment was to audit and clean out my wardrobe to curate my dream wardrobe.

This is an ongoing process; it is not something I can do in one week, but I am making progress. Their criteria for evaluating items are helpful:

1. Is the item consistent with the words I now use to describe my style?

2. Does the item work for my lifestyle today?

3. Does it feel good to wear, physically and emotionally?

4. Do I have too many similar pieces?

5. Is the item in poor condition and needs to be discarded?

I have given away some redundant items and tossed some worn and stained things. I am getting closer to having a curated collection of clothes and accessories.

Along with these actions, I am reorganizing my storage to support combining pieces to create outfits and to add accessories to achieve finished looks.

My path forward

The last two weeks of the INDYX course provide suggestions for creating a Wishlist and testing their recommendations for sourcing one or two items from the list.

Their guidance is in tune with real life constraints. The sort of overhaul I want for my wardrobe is both minimal and maximal at once. It is going to be an evolving process.

For the present, I am shopping my closet for attractive outfits with renewed focus and understanding.

I will never become a fashionista, but over time I intend to transform my rather dull jeans + tee uniform into a spirited style that more accurately reflects my personality. It’s going to be fun!

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Dunelair
Crow’s Feet

: Friend, reader, and photographer with eclectic interests. Loves living on California's central coast. Born and raised in West Virginia.