I hate dressing myself

The pressure of finding the perfect outfit

Jun 01, 2026

I gasped when I saw the dress on the mannequin.

My mom and I had walked into a Magazine Street shop in search of an outfit for my SuperBloom Party, which was only a few days away.

While I was looking forward to the event, my outfit had been a persistent source of stress.

For the last several years, I’ve struggled to find clothes that feel like “me.” My body has changed shapes and sizes, and my sense of self has continued to evolve as I’ve gotten older.

I keep asking myself: How do I want to feel in my clothes? How do I want to be perceived?

Each day, I find it exhausting to decide what clothes to put on this human form of mine.

For the party, I wanted to feel vibrant and on-theme. I knew I could find something vaguely floral from my closet, but nothing felt right until I saw the mannequin.

The bright colors of the floral print dress aligned perfectly with what I envisioned myself wearing as I publicly announced my new business, Strategic Vacations.

The dress was particularly perfect because it was from SchweiStyle, my client and friend Katharine Schweighardt’s vintage business. Beyond the aesthetics, the dress felt like an embodiment of my vision for Strategic Vacations and the impact my coaching practice could have.

Katharine and I met years ago in the bathroom at a friend’s wedding. She had a gorgeous tiger brooch and a delightful sense of style that immediately evoked conversation.

I’d soon learn that she was burned out, having spent years in operations for a charter school network. She became a coaching client, working with me in a variety of formats over many years.

Fast forward to today, and she describes SchweiStyle as, “A secret dream that never felt truly possible.”

She’s made that dream a reality and you can now buy SchweiStyle at The Good Shop, at The Columns Hotel, and on Etsy.

Remembering our conversations about her style choices and aesthetics, I shared that throughout our work together, it felt like a vintage business had always been a twinkle in her eye.

She told me, “I have been preparing for years for this, long before I was able to articulate it aloud to someone.” She went on to say, “Any time I’m in your orbit, I’m pushed and inspired about what’s possible.”

Katharine has a gift for finding beautiful, wearable vintage and for giving women permission to make bold style choices.

It’s been exquisite to see her grow SchweiStyle and her impact, and it was a particular treat to surprise her at the SuperBloom Party wearing a dress she’d sourced.

The dress made me feel like my body was wrapped in my client and friend’s success. I felt emboldened and confident.

Huge thanks to Katharine for the outfit and to the 50 people who attended the SuperBloom party. It was unforgettable.

With such love,
Lelia

Katharine’s post on LinkedIn about our work together was deeply meaningful to me. I’m thrilled to share it here with her permission.

“I am forever grateful for the impact that working with Lelia has had — and continues to have — on my life and career.

Lelia is the kind of thought partner who truly gets it: the overwhelm, the pivots, the ambition, the messy middle, all of it.

She’s also insanely joyful and really fun to be with.

Lelia provided the space to think about my different identities and experiences and recognize what opportunities I have now.

Working with her has helped me feel more grounded, clear, and confident in seasons of transition and growth.

I highly, highly recommend connecting with Lelia if you’re a woman at a crossroads, feeling overwhelmed, or looking for someone who can help you move forward with both strategy and heart.

- Katharine Schweighardt

Curious about working together? I’d sincerely love to have a free 30-minute conversation. No prep needed. Bring your messy middle. :)

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