Why Men Regret Underdressing More Than Overdressed | A SUITBAE Guide
Why Men Regret Being Underdressed More Than Overdressed | A SUITBAE Guide
Most men worry about one thing when choosing what to wear:
“I don’t want to look like I’ve tried too hard.”
But in reality, that’s rarely what causes regret.
What men almost always regret is the opposite — realising too late that they didn’t dress smart enough for the moment.
This guide explains why underdressing lingers longer than overdressing, and how to avoid that feeling altogether.
Regret Comes From Visibility, Not Comfort
When someone feels overdressed, it usually passes quickly.
They take their jacket off. They relax into it. The feeling fades.
When someone feels underdressed, it does the opposite.
It stays with them all day — because underdressing is visible, especially in photos, formal settings, and milestone moments.
Why Underdressing Feels Worse
- You feel out of place
- You second-guess yourself
- You become aware of your outfit instead of the moment
That awareness is what causes regret.
Overdressing Is Easier to Correct
Being overdressed is flexible.
- wear your jacket open
- remove it later
- relax into the outfit
Being underdressed offers no correction.
You can’t add structure once you’re there.
Photos Are Where Regret Shows Up Most
At the time, an outfit might feel “fine”.
Months later, in photos, the difference becomes obvious.
You don’t notice who was slightly overdressed. You always notice who didn’t quite look right.
Suit Examples That Help Avoid Underdressing
These suits quietly prevent regret — they’re structured, appropriate, and flexible enough to relax into as the day goes on.
Lawrence Navy Three-Piece Suit
A three-piece navy suit looks correct at almost any formal event and still feels appropriate when worn open later. It gives you margin — which is exactly what prevents regret.
Jake Midnight Three-Piece Suit
Midnight blue sits slightly smarter than standard navy. It photographs cleanly and works from day into evening without feeling heavy.
Diablo Black Three-Piece Suit
Black removes doubt entirely. When the concern is “what if I’m underdressed?”, black answers that question immediately.
FAQ: Dressing for Important Events
Is it worse to be underdressed or overdressed?
Underdressed. It’s more noticeable, harder to correct, and shows up clearly in photos.
How can I avoid underdressing?
Lean slightly smarter than you think you need. Structure gives you flexibility later.
Why do three-piece suits help?
They keep the outfit looking intentional even when jackets come off.
Does colour matter?
Yes. Navy, midnight blue, and black are safest when you’re unsure about formality.
What’s the safest option if I’m unsure?
Choose a structured three-piece suit — you can always relax it as the day goes on.
Regret doesn’t come from trying too hard.
It comes from realising you didn’t try enough.
When in doubt, choose the option that lets you relax later — not the one you’ll wish you could improve.
SUITBAE — Made for the moments that matter.