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A Gentlemen's Guide on What to Wear on a Casual First Date

A Gentlemen’s Guide on What to Wear on a Casual First Date

Some research says you only have 27 seconds to make a good first impression. Clothes, facial expressions, actions, and speech all count.

So figuring out what to wear on a casual first date is super important!

Most first dates call for a laid-back attire. You do not want to put extra pressure on the date or seem too stuffy. But at the same time, you want to look like you have made an effort and care about your appearance.

It is difficult to find that middle ground. This guide will help you decide what to wear on a first date so you can start the (potential) relationship as you mean to go on.

Casual First Dates Call for Collared Shirts

T-shirts are casual, but collared button-down shirts are first date casual. If you are a man dating a woman, she will likely see a collared shirt as a sign of you making an effort.

For a casual coffee or drinks date, choose a light denim shirt over a plain white (or striped) t-shirt. Button it up or leave it open, that is up to you. Pair the light denim shirt with dark-colored jeans to sidestep a potential double denim fiasco.

If you are going to watch a concert or movie, choose a cotton flannel shirt over a graphic t-shirt.

Dinner dates call for a more structured, long-sleeved collared shirt. Choose one with a fun pattern that you feel comfortable in. You can still wear a plain t-shirt underneath if you prefer, but keep it buttoned up.

There are certain types of casual first dates where you can get away with a t-shirt:

  • Hiking/sport
  • Mini golf
  • Beach

But for any other casual first date, opt for a collared shirt. Never wear anything sleeveless.

Scrubbed up Sneakers or Work Boots

The main thing to keep in mind when considering your first date attire is to wear clothes that are clean and presentable. This is 100% the case with shoes. Even clean running shoes are better than muddy boots.

That said, nice white sneakers or leather boots are preferable to compliment a first date outfit for men. But make sure they are everyday-wear sneakers and not gym shoes.

Jacket and pants Levi’s, sneakers Sandro

Steer clear of oxfords or brogues (too formal) and loafers or sandals (too informal). You must wear socks on a first date. That is non-negotiable.

Can’t Go Wrong With Jeans

Jeans are the Goldilocks of casual first-date attire. Not too formal and not too informal. Perfect.

If you are struggling to find a great pair of jeans, opt for a dark pair with straight legs. But do not dull your personal style because you are on a first date. If you love grey skinny jeans or acid wash ripped jeans, you do you.

For those who do need style help, avoid chinos, khakis, and any other type of pants. You risk looking too smart.

Considering jean shorts or board shorts? No. One thousand times no. 

If you need to wear a belt with your jeans, a simple black or brown leather belt is spot on. If you are wearing leather shoes, pick a leather belt to match.

Jackets Yes, Hoodies No

Jackets are easy when you are deciding what to wear on a casual first date. Almost anything goes!

Jean jackets are okay if you are wearing black jeans or vice versa. As long as they are in contrasting colors, you will pull the look off.

Bomber jackets and soft black leather jackets are easy wins. A nice wool sweater is fine if that is your style and the weather does not call for a jacket.

If it is cold, opt for a wool pea coat and thin scarf.

Never, ever, ever wear a hoodie as part of a casual first date outfit. Unless you are 13-years-old and you are going to an arcade. Dress your age and do not forget to dress like you are making an effort.

Tone Down the Accessories

You might be a dude who pulls off the “dripping in jewels” look. In which case, stick with your vibe! But if you are a guy who does not wear a lot of accessories in everyday life, a first date is not the time to start.

A watch and a belt are all you need. You can wear a beanie and gloves if it is cold. But otherwise, leave the headwear at home.

Do Not Skip Your Grooming Routine

It does not matter if you look like Leonardo DiCaprio on your first date if you smell like his character in The Revenant

Shower, shave and brush your teeth before a first date. Before any date.

Make sure your fingernails are clean. Beautiful smelling cologne is a worthwhile investment. 

But that is it! Again, a little bit of extra effort goes a long way which is also one of the best relationship tips and advice for men.

Which Shaving Razor Is Right For You? Here's What You Need To Know

You do not need to reinvent the wheel for your first date outfit. Style your hair how you always style it. Now is not the time to try something new. Present an elevated version of your most authentic self.

Bonus Casual First Date Attire Tips

Learning what to wear on a casual first date is important, but how to wear casual first date attire is important too. Here are some other style tips:

  • Feel comfortable in what you wear
  • Make sure the clothes fit you well
  • Wash and iron the clothes
  • Check the clothes for stains, holes, and rips

If you are going to dinner on your first date, it may be a good idea to wear black if you are nervous. You do not want to spill spaghetti on a white shirt!

And in case the date goes in a particular direction, wear your best underwear. Nothing wrong with being optimistic, right?

Wojtek Czerski is modeling part of the new Linen Collection Spring 2016 for UNIQLO USA. Including fresh items like Lightweight sweaters and cardigans made from high-quality French Linen.

Now You Know What to Wear on a Casual First Date

When considering what to wear on a casual first date, the most important thing is that you feel comfortable. If you think you have made an effort and look great, then it is likely you do. He or she is bound to agree if they are the right person for you.

Do not stress about it too much, and have fun!

Like this article? Check out our other style posts for more tips and advice.

  1. Totally right this article. Great options.

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