QUESTION

"Can I wear flip-flops at work?"

MY TAKE

It depends on the flip-flop—and it depends on your workplace.

Think about flip-flops the same way you think about athletic shoes. You probably wouldn’t wear the sneakers you work out in to the office, even if your workplace is business casual. Beach flip-flops belong in that same category.

A polished leather sandal or elevated slide is a different conversation.

Shoes don’t exist in isolation. They’re part of the message you’re sending.

One question I always ask is: Do these shoes look intentional, or do they feel like an afterthought?

The shoes you choose help communicate whether you dressed with purpose—or simply grabbed the closest pair by the door.

TODAY'S MOVE

Before you leave the house, look down. Ask yourself whether your shoes support the impression you’re hoping to make.

QUESTION‍

"Is There Such a Thing as Being Overdressed?"

MY TAKE‍

Yes—but most people who ask me this question aren’t.

More often, they’re worried about standing out. There’s a difference between being overdressed and being stylish, and the two are often confused. A ball gown at a backyard barbecue is probably overdressed. Shorts at a black-tie wedding probably are, too. Context matters.

Being stylish means developing good taste. It means understanding how the pieces of an outfit work together and putting them together with intention. If someone compliments you because you look polished, put together, or well dressed, that doesn’t mean you’re overdressed. It often means your style is communicating exactly what you hoped it would.

Many people dim their own light because they worry they’ll make someone else uncomfortable. Showing up as a smaller version of yourself rarely feels authentic. Once you’ve read the room, there’s plenty of space to let your personal style come through.

TODAY'S MOVE

The next time you wonder if you’re overdressed, ask yourself: Am I ignoring the context, or am I simply uncomfortable being noticed?

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