👕 From Fashion Disaster to Style Connoisseur

3 tips for finding your fashion groove

Good Afternoon!

Welcome to a late Wednesday edition of Daily Self, I’m happy to see you today. For our new subscribers, Wednesdays are dedicated to physical self-care topics. Today’s focus is on clothes—a topic that I previously cringed at even thinking about.

Here’s what you’ll find inside…

1. Afternoon Microdose: 👕 From Fashion Disaster to Style Connoisseur

2. Myth of the Day: Replaced with fashion influencers

3. Action Item: Is it time to excavate your closet?

Let’s get started!

(1) Afternon Microdose

👕 From Fashion Disaster to Style Connoisseur

When it comes to appearance and how we present ourselves to other people, the clothes and shoes we wear are probably the easiest to change. You could argue that getting a haircut is as simple as picking up a pair of scissors; however, there is a horrifying semi-permanence to it (anyone who’s ever had bangs will agree).

Clothes and shoes are fluid, simple to change, and can be adjusted all at once or one small component at a time. Even with little to no money, it’s possible to trade clothes online with Poshmark, ThredUP, and Ebay, or through brick and mortar stores like Crossroads.

Over the last couple months, I’ve been slowly “rebranding” myself, and a big part of this has been updating my wardrobe. Every time I go through a personal rebrand, there’s an significant shift in what I wear, and the way I present myself. When I started my self-care company, for example, I was mainly meeting and working with hikers and backpackers. This led to me purchase 90% of my wardrobe from REI.

This time around, I’m rebranding based on my new identity as a personal development writer. Age is also a factor; as a 42-year-old semi-silver fox, I’m not sure a baggy graphic sweatshirt with high-waisted jeans and Birkenstocks is the right look. Here’s what I’ve learned during my wardrobe odyssey.

3 lessons learned from a former fashion disaster

1. You look better in a $100 outfit that fits perfectly than in a $500 outfit that fits poorly. When something fits well, it looks like it was made for you. If clothes are consistently too big or too small at the stores you shop at, go to different stores. For example, I’m 5’6”. If I go to Banana Republic, everything I try on is made for someone 4 inches taller than me (even a small). The patterns are based on taller models, which means that NOTHING from Banana Republic ever fits well. Luckily, I discovered a store near me that specifically works with designers who make clothes for men 5’8” and under. Now, my clothes actually fit well. Essentially, find stores that sell clothes specifically made for people with your body shape.

   

2. Dress your persona. When I was shopping at REI for all my clothes, I was shopping for the “outdoorsy hiker who owns a backpacking gear company and goes to the mountains every weekend” persona. Now, I’m shopping for the “mature LA-residing self-development writer” persona. TOTALLY different personas. If you are considering your own rebranding, think about your target persona—i.e. who do you want people to see you as when you meet them for the first time? Shop at stores and buy clothing that aligns with that vision of yourself.

   

3. Invest in high-quality foundational pieces. Rather than suggest “dress for the occasion” which is what everyone else says, I suggest categorizing the occasions you wear clothes for (yes, I can think of several occasions that do not require clothes 🍑), and buying foundational pieces for those categories. Foundational pieces are the items that can be worn with nearly anything and that you will wear the most often (e.g. black shoes, black coat, dark-wash jeans, lightweight leggings, etc.). Categories may include work, lunch out, dinner with friends, dinner date, high-energy party/nightclub, mid-energy adult socializing, low-energy Netflixxing, sports/recreation, etc. Buy high-quality pieces that will last you a lifetime—or at least, the lifetime of your persona.

   

(2) Myth of the Day Fashion Influencers

In place of the Myth of the Day, I wanted to share some examples of #2: Dress your persona:

⚪ Harry Styles (pearls!) has become known for his gender-bending and eclectic fashion sense, which often includes bold prints, statement accessories, and vintage pieces. His style has inspired a new wave of gender-neutral fashion, with Gen-Z embracing more fluid forms of self-expression. Timothée Chalamet (again, pearls!) in a similar way is recognized for his unique gender-neutral and avant-garde style.

💚 Billie Eilish is known for her oversized silhouettes, neon colors, and quirky accessories such as bucket hats and chunky sneakers. Her style has become emblematic of Gen Z fashion, where comfort, individuality, and sustainability are prioritized over traditional notions of glamour and luxury.

👩🏿‍🎤 Lizzo is known for her bold, colorful, and body-positive style. She is unapologetic about her curves and often wears outfits that accentuate her figure. One of Lizzo's signature looks is the bodysuit, which she often wears in vibrant colors and prints. She has also been seen wearing jumpsuits, crop tops, and thigh-high boots, all of which showcase her confidence and individuality.

(3) Action Item

Are you in a state of rebranding? If so, put some thought into how fashion plays into it, and whether or not your new persona dresses like your old persona. If not, then it may be time to excavate that closet of yours!

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