The Modern Man's Guide to Cocktail Attire

I recently received an invitation to a charity event requesting "cocktail attire," and I have a confession: I still looked it up.

While I had a general idea, I always need to double-check these things. Why? Because as time moves forward, so do the rules of dressing. There are the established traditions of menswear, and then there's the modern reality, where comfort and confidence play a huge role. You can feel overdressed, even if you technically aren't.

Given that, I put together a quick guide on nailing cocktail attire, including where you can strategically bend the rules without breaking tradition entirely.

What Exactly Is Cocktail Attire? 

The term originated in the 1920s, referring to a dress code for semi-formal events. I've always suspected it was born out of convenience—allowing gentlemen to transition straight from the office to an evening event without a complete change, in an era when men dressed sharply every day, that made perfect sense.

Today, however, it means putting in a little effort—ditch the tech polo and golf shirt!

Key Pieces: What to Wear

Cocktail attire is less formal than Black Tie (semi-formal) or White Tie (overtly formal). You're aiming for a sharp, sophisticated look that pays tribute to its origins.

• The Suit: A classic, understated suit is your best bet. Focus on darker tones, such as navy, charcoal gray, or black.

• The Shirt: A crisp white dress shirt is a timeless foundation.

• The Shoes: Ground the look with an elegant shoe, like a round-toe Oxford or a Double Monk Strap.

Where to Bend the Rules:

• The Tie: I would wear one to complete the look, but depending on the event's atmosphere, you may be able to skip the tie. This is where you can assess the setting.

• The Pocket Square: Do not skip this. You must "finish" the outfit. A pocket square is the essential final detail. Always.

Are Sport Coats Acceptable?

Traditionally speaking, no. Cocktail attire calls for a suit.

However, this is the most significant area for modern interpretation. Please know your setting and who else is in the room.

• If you're hosting or if the event is more relaxed, you can get away with it.

• If you opt for a sport coat, choose a dark navy or another deep color and avoid loud, over-the-top patterns.

• The goal is to be comfortable while looking dressed up. A sharp sport coat can achieve this without sacrificing sophistication.

What I Saw at the Event

At the recent "cocktail attire" gathering I attended, the dressing spanned the spectrum:

• Most people wore sharp suits.

• Some wore nice sport coats.

• Others clearly missed the mark, showing up in golf slacks and white athletic shoes.

Don’t be the golf slacks guy. A little effort goes a long way.