What you wear on a first date sends a powerful message—often long before you say a word. In this episode of Getting Inside the Right Male Mind, Lisa and Benjamin Shield explore how overdressing and underdressing can quietly sabotage attraction, connection, and second dates. From men’s visual wiring to the difference between style and costume, this conversation reveals how clothing choices influence a man’s ability to relax, connect, and imagine a future with you, all through the lens of authenticity and emotional availability Lisa and Benjamin return from a brief hiatus to tackle a deceptively simple but critical dating topic: how you dress on a date—especially the first one—can make or break connection. They explain that because men are highly visual and first impressions are lasting, both overdressing and underdressing can create emotional distance. Over styling can make a woman seem high-maintenance, insecure, unapproachable, or more like an image than a person. Underdressing, on the other hand, can signal disinterest, low effort, or lack of care. Throughout the episode, Benjamin shares how men unconsciously extrapolate what a woman’s appearance means for long-term compatibility—imagining daily life, social settings, family introductions, and future ease. Lisa emphasizes that dating is not a fashion show, but an opportunity for authentic connection. Together, they highlight that true attraction comes from comfort, approachability, and clothes that move naturally with a woman’s body, allowing her real essence to come through. The episode ultimately reinforces the core philosophy of Emotionally Naked Dating: authenticity—not performance—is what creates lasting love
Men form strong first impressions visually—and those impressions are hard to undo
Overdressing can signal:
Underdressing can signal:
Men subconsciously ask:
Clothing that feels like a costume blocks authentic connection
Too much makeup, jewelry, fake lashes, extreme heels, or overly sexualized outfits are common turn-offs
Showing too much skin can create mixed signals and embarrassment rather than attraction
Comfort in one’s body is one of the biggest turn-ons for men
Classic, understated, well-fitted clothing is often the safest and most attractive choice
A crisp white button-down, flattering jeans, and comfortable boots are suggested as a reliable first-date outfit
Dating is about approachability, warmth, and emotional availability—not dazzling or performing
Authenticity allows a man to imagine a future, not just admire an image