What Should You Wear?

It was a nice restaurant—nicer than I thought it would be.

I was dressed in jeans, a polo shirt, and running shoes. I looked around to compare my clothes to what everybody else was wearing.

I was underdressed.

They were mostly in suits. Everybody was dressed in grey, blue, or black, and there were a few stylishly dressed women in bold colors and high heels.

I was underdressed—big time.

I was standing in the entry area right near the host stand. The space opened into the dining room.

Was it my imagination, or were they staring at me? I could feel heads turning.

I had to be imagining that anyone was paying attention. I knew intellectually that I was just being paranoid, but it felt like people were staring at my running shoes.

Yeah, total paranoia. It had to be.

I chatted with the hostess. “I’m underdressed for this place,” I said with a smile. “Maybe I should come back another time.”

She wasn’t going to let me leave. “Oh, no” she said, glancing at my jeans. (They weren’t even the fancy $350 jeans you probably wear: they were from Target.) I could feel my face turning red.

“You’ll be fine,” she said as she pulled together menus and started walking me across the room to a table.

My paranoia was going full force now.

They had to be staring.

They had to be wondering, “What’s the repair guy doing here in the middle of the dinner service? Is he going to start hammering now?”

I’m sure they were wondering whether I’d lost my tool belt.

I didn’t look at them in their suits, ties, and shiny shoes. I just walked with my eyes straight ahead.

I got to my table, sat, and hid behind the menu.

My paranoia subsided once I disappeared into my table, and I shifted gears to some of my other anxieties.

You Need to Match More Than Your Socks

Have you ever felt awkward about your appearance? Is it just me?

I’m pretty sure I’m not alone in this.

Right? I’m not alone? Right?

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We want to fit in. We want to feel comfortable in the group.

Come on, tell me I’m not alone in this, okay?

Okay, okay, enough about me…let’s talk about you.

What does this analysis of my neurotic tendencies have to do with anything pertinent to your life?

When you’re building your network by taking folks to lunch, breakfast, coffee, etc., you need to dress like they dress.

You need to help them feel comfortable. You need to match their clothing choice.

When you’re trying to make a favorable impression, the last thing you want is for them to have in their head the conversation I had with myself as I entered that restaurant.

You want them to feel like they’re in the right place, at the right time, with the right person.

You don’t want them obsessing about why you’re in a suit and they’re in jeans and a t-shirt and how awkward they feel.

If they feel awkward and uncomfortable, you’re losing.

When they’re feeling off, they’re not connecting with you. They’re not getting to know you, like you, and trust you.

When they’re feeling awkward and uncomfortable, they’re associating it with you. That’s not good. You want them to associate happy thoughts with you. When they think of you, they should think of rainbows and sunshine, not deep-seated anxiety.

Got it?

How to Get in Sync With Your Prospective Referral Sources

So what do you wear to coffee?

You don’t need to call them and ask them what color shirt they’re wearing. You don’t need to match them item for item.

You do, however, want to be in the zone they’re in. You want to be close, especially at the outset of the relationship.

If they’re wearing a t-shirt and jeans, you can get away with business casual. The same is true if they’re in a suit: business casual is fine for you.

You don’t, however, want to be in a suit if they’re in a t-shirt and jeans at Starbucks. That’s a pretty big gap.

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You just need to be in the same clothing range so they’ll feel comfortable.

You should give fair warning if you’re taking them somewhere that’s dressier than some might expect. Let them know in advance.

Bottom line: They need to be comfortable, and you need to make sure they are by giving them information when clothing may be an issue and by matching them in terms of the level of formality.

Dress like they dress, and they’ll connect with you. It’s one thing to walk into the restaurant alone and underdressed. It’s a whole different thing to walk in with your friend who’s dressed just like you.

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