😎 Is your attire killing your deals?

There's a narrow window between "unprofessional" and "trying too hard" on video calls, and most remote sellers miss it.

January 21, 2026

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IN THIS EDITION

  • How sales people really feel about fake urgency

  • Why this gay sales manager is suing the Steelers

  • The Quarter Zip Doctrine

  • If paying out commissions is a pain, this is for you

  • And more…

LIVE FROM THE SALES FLOOR

Tips + Tricks

Other Stuff

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BOS PODCAST

This week on the Because of Sales Podcast:

Newsletter growth, Sponsorships and monetization, AI conducted interviews, Claude Cowork and AI tools, Business model types and the corresponding sales roles, Remote sales attire, Personal branding, Referrals and organic sales growth.

You can listen on Youtube, Spotify, or Apple.

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SELLER’S SECRETS

The Quarter Zip Doctrine

There's a narrow window between "unprofessional" and "trying too hard" on video calls, and most remote sellers miss it.

We talked about this on the pod after seeing Casey Woodard's take: if you're a high-ticket closer, the only acceptable outfit is a quarter zip. Show up in a dress shirt, and you look like you're LARPing as a professional. Show up too casual, and you look unprofessional and childish.

Quarter zip only. According to Casey.

Here's why it matters more than it should: remote selling stripped away most of the context clues buyers use to assess credibility. They can't see your office, your team, or how you carry yourself in a room. All they get is your face, your voice, and what you're wearing from the chest up.

That's the entire canvas.

When you overcorrect with a full suit or dress shirt, you're signaling that you think this is formal. It reads as compensation. Like you're performing professionalism because you don't naturally have it.

When you underdress (hoodie, T-shirt, whatever), you're telling the buyer this call doesn't warrant effort. That might work if you've already built trust or your role is purely transactional. But in certain fields, you're cooked before you start.

The quarter zip sits in the middle. It says: competent, put-together, not trying to impress you. It's the uniform of someone who does this every day and doesn't need to prove it.

This isn't about fashion. It's about removing friction. Every little thing that makes a buyer pause, even subconsciously, costs you momentum. And on a video sales call, momentum is everything.

The dress code debate is really a trust-building debate. What you wear is the fastest, easiest thing to control. It won't close deals for you, but it can kill one before you get started.

If you're on camera selling anything above $5K, default to the quarter zip. You can experiment once you've built enough credibility that what you wear stops mattering.

Until then, stay in the window.

Where do you fall on the sales attire spectrum?

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