Shorts, Flip-Flops, and Investor Meetings—What Really Matters in Business Dress Code?
Dress codes are really trust codes. Show up prepared, deliver results, and the flip-flops become a talking point—not a disqualifier.
Shorts, Flip-Flops, and Investor Meetings—What Really Matters in Business Dress Code?
Lesson: Comfort Over Costume
My default outfit? Shorts and flip-flops—even at investor meetings or speaking engagements. I’ve shown up to conferences, boardrooms, and client sites wearing what looks like vacation gear. Reactions range from chuckles to awkward reminders that “next time we’d prefer slacks.” My most buttoned-up moment was a sports coat in Des Moines; locals still joked about how laid-back Californians were while I felt so uncomfortable all day trying to be dressed up.
Insight: Skill > Suit
- Competence Trumps Clothes – Your value is your expertise, not your lapel width.
- Confidence Is Contagious – If you’re comfortable in your own skin, people relax too.
- Context Still Counts – Sometimes the venue requires dialing it up a notch—but only to respect the audience, not to mask insecurity.
Dress codes are really trust codes. Show up prepared, deliver results, and the flip-flops become a talking point—not a disqualifier.
Action Item: Define Your Personal Dress Spectrum
- Pick a Comfort Baseline – What lets you perform at your best without being distracting to your work.
- Identify Mandatory Upgrades – Boardroom? Court appearance? Funeral? Know your limits.
- Communicate Early – If attire matters to a client, ask upfront and avoid surprises.
Your Turn:
Do suits empower you or suffocate you? Let's talk about your dress-code philosophy—I’d love to compare wardrobes (or lack thereof like mine).
