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The coolest cocktail attire for men: How to style yourself

Strike the right chord with the perfect ensemble

Man in a suit
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It may feel like the world has been getting more and more casual over the last few years. Especially during the “year that will not be discussed,” but the truth is, fashion is beginning to shift back the other direction. As the vintage looks are starting to return to prominence, you will likely begin receiving invitations to cocktail parties, get-togethers, and more with the label “cocktail attire.”

Deciphering dress codes is something we do here, what is business casual? What is the difference between business casual and smart casual? When it comes to cocktail attire for men, there are some rules, and there is some wiggle room. Here is what you need to know.

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What is cocktail attire for men?

Man wearing suit with boots
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Cocktail attire falls on a similar plane as business professional. If you were to look at a hierarchy of formal dress, this is what it would look like:

  1. White tie: Think tuxes with white vests, ties, coattails, and even sometimes top hats (someone invite us …)
  2. Black tie: Think prom and most weddings you go to. Basic tux and mostly black vests and ties.
  3. Black tie optional: This is one of those times when people say one thing and mean the other, they are just being nice. It usually means they want you to wear a tuxedo, so just do it.
  4. Business professional: What it sounds like. Think Harvey Specter in Suits. Suits in basic colors. Ties in subtle patterns and solids. Shoes in classic form. This is appropriate for the office.
  5. Cocktail attire: The best way to define this is business professional with personality. It’s going to feel very similar to the above; only you can feel free to wear things you wouldn’t normally wear to the office.
  6. Smart casual: Elevated version of business casual. No polos or denim here. Dress pants and dress shirts. Everything is sharp and high quality.
  7. Business casual: Have you seen your IT guy lately? That is what it is. Almost a standard uniform of chinos and a polo with hybrid dress sneakers.
  8. Casual: Wear whatever you want, just be covered.

What is the perfect cocktail attire outfit?

A man in a suit looking in a mirror
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The perfect cocktail attire look is going to, of course, depend on the kind of place you are going, the time of day, the people attending, and on and on and on. But there are some things you can look to that will help you stay on the right path. Here are some ideas for you to keep in mind when you’re looking for inspiration.

The suit

Tailor stretching measuring tape across suited chest
Pressmaster / Shutterstock

The best thing about a cocktail attire event is that it is the best time to break out all those things you can’t or shouldn’t wear to the office. The wild tie, the bright suit, the crazy shirt, all of those things are going to be tempting. However, keep in mind that you want to look like a stylish man, not a kaleidoscope.

For your event, if it’s after 6 p.m., which most of these events are, then you want to stay more on the darker side of the spectrum. Black may feel too aggressive and charcoal and navy may feel too much like the office. This is when you want to break out that burgundy suit your partner told you was a waste of money because you would never wear it or the forest green one that always felt a little too loud for the office but still has a dark hue to its mystery.

You can also play with patterns a little, too. If you have a charcoal or navy suit with a pattern that felt a little too much for the office, then this is the place you can try out and see if it fits the after-6 p.m. vibe.

The shirt

Button-up shirts on hangers
Nimble Made / Unsplash

The truth is, there is never a wrong time to wear a crisp white dress shirt. It is the perfect partner to any suit, any tie, and any overall look. However, you get to wear one of those any day of the week at the office, so it’s best if you try to pair something else with your ensemble. Go the same route as the suit and grab yourself a darker hue of a color like burgundy, navy, evergreen, or even a black if there is enough contrast with your suit.

Solids in the shirt make the tie easier to go all out with, but don’t be afraid to pick up some pattern as well. If you want to do a subtle check or a stripe, that goes a long way to give your look depth that your business professional looks often lack. One thing to keep in mind: If you can make it happen, a French cuff is always going to look stellar here. It also gives you a great reason to break out a pair of cufflinks to catch people’s eye.

The tie

Man adjusting his tie on suit
Ruthson Zimmerman / Unsplash

If you’re showing off personality, most men go with the tie. That’s because we have been sold novelty ties since Mugatu designed the piano key tie in the ’80s. Please, for everyone’s sake, leave the novelty ties at home. That doesn’t mean you can’t throw some color in there, just don’t be obnoxious with it.

Instead, go with one of two approaches: 1. Stark contrast. If you’re wearing a solid shirt, do a paisley tie. 2. Monochromatic. If you’re wearing a navy suit with a navy shirt, don’t stop there. The second look may feel a little boring, but there is something to be said about perfection. A well-fitting, perfectly monochromatic look is insanely attractive. Just ask John Wick.

The shoes

Brown double monk shoes
Jia Ye / Unsplash

When it comes to the shoes, we have one major thing to say: Whenever possible, this is where you should be wearing your black dress shoes. Your dark brown dress shoes may be needed if you are electing to go with a dark navy (although, if you have a bright enough navy, black shoes can look great — just be careful that it doesn’t look like you thought you were wearing a black suit and the light changed on you). Your tan dress shoes should be left in the closet. They get enough wear around the office.

This is also the perfect time to wear your sleek black Chelsea boots that you always feel are a little too much for the office. Slide these on with your monochromatic look and you will be the talk of the party. Another piece of advice, if you are wearing a burgundy suit, avoid the black dress shirt and black Chelsea boots, unless you’re hoping for Martin Scorsese to cast you in the next mafia flick.

Finally, don’t forget the accessories. Pop a pocket square into your chest pocket for a dash of color. Take out the watch you’re afraid to damage other places. And if you are a fedora guy, go for it. Just take it off when you go inside. Have fun and be safe.

Mark D McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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