The Ultimate Style Guide: What to Wear on a First Date

Choose your first date outfitBy Erika Ettin

I used to love the show “What not to Wear” with Clinton Kelly and Stacy London. (In fact, I was actually an extra once when they filmed an episode in Washington, DC… I couldn’t resist!) On the show, Clinton and Stacy dressed up their clients like they had never been dressed before. I want to highlight one of the outfits that holds the most importance — the first date outfit.

Now, I’m not saying we should all be fashion experts. I wouldn’t know a name brand pair of jeans if they bit me on the nose. But for the first date, whatever you’re wearing, it’s important to put yourself together nicely. First impressions are the key, especially in a world where it’s so easy to move on to the next person with a click or a swipe.

The Basics

Some first dates are right after work, for perhaps a happy hour cocktail, so that’s easy since you’ll just come in your work clothes. Be sure, though, to put a bit more thought into getting dressed that particular morning. For women, a nice business casual outfit works well, but try not to look too “business” and no fun. A nice pair of pants or skirt and a top that shows off your shape but isn’t too revealing works well. Save the low-cut, curve-hugging stuff for going dancing Saturday night. And save the buttoned up black and gray shirts for the board room. A pop of color always goes a long way in terms of being both feminine and memorable. Studies have actually shown that red is the color of choice if you’re looking to make a great first impression. When it’s cold, try not to wear anything like a huge turtleneck because it makes you look somewhat closed off. And in the winter, a good pair of tall boots can always be very sexy.

Red is the color of choice

Iron, Iron, Iron

For men (and women), all I can say is that the iron is your friend. I can’t think of anything worse than someone showing up in clothes that are completely wrinkled. I’m not even saying you need to iron anything yourself! I often bring my shirts to get dry-cleaned because I really just want them pressed. Other than that, just go with your style. Check your teeth, make sure there are no stains on your shirt, and you’re good to go.

For the dates that aren’t after work — perhaps a weekend coffee or a walk — a good rule of thumb is to dress to match the venue or occasion: Elegant bar? Elegant outfit. Casual coffee shop? Casual outfit. Outdoor hiking? Something sporty.

Here are a few additional pointers to keep in mind:

  • DO wear something that makes you feel confident and attractive. (This is the most important.)
  • DON’T wear something you took out of your hamper and Fabreezed.
  • DO dress in a style that’s “you,” even if it defies the norm.
  • DON’T second guess your fashion choice once you’re on the date. Own it.
  • DO flatter your best features but not in an over-the-top revealing way.
  • DON’T forget that your clothes will never outweigh hygiene. Make sure you’ve brushed (hair and teeth) and shaved.
  • DO have a few go-to outfits ready so you never have to stress out about it.

With all of this said, if you do go on a date with someone you consider to be a “bad” dresser by your standards, it’s important to remember that while his/her personality may not change, the wardrobe can, so try not to let it be a deal breaker. In the end, while the clothes make the first impression, someone’s values and personality make the lasting one.

For more first date tips from another dating expert, read about why you should get raw and vulnerable on your first dates.



Disclaimer: We work hard to offer you valuable and reliable information about all of the products and services we review. In order to provide you with this free service, we use links on our site that provide us with commissions for referring you to the seller's site. We guarantee that this does not influence the material we present, but may influence the positioning on our site, and only supports our efforts to offer you the best and most relevant information possible.

Advertising Disclosure

This site is a free online resource that strives to offer helpful content and comparison features to its visitors. Please be advised that the operator of this site accepts advertising compensation from companies that appear on the site, and such compensation impacts the location and order in which the companies (and/or their products) are presented, and in some cases may also impact the rating that is assigned to them. To the extent that ratings appear on this site, such rating is determined by our subjective opinion and based on a methodology that aggregates our analysis of brand market share and reputation, each brand's conversion rates, compensation paid to us and general consumer interest. Company listings on this page DO NOT imply endorsement. Except as expressly set forth in our Terms of Use, all representations and warranties regarding the information presented on this page are disclaimed. The information, including pricing, which appears on this site is subject to change at any time.


The Best Dating Sites

Must Read

How much does Zoosk cost?

Zoosk Cost: Get the Full Pricing Plans

Read more
match free trial plans to find love

How to Use for Free

Read more

How to Choose a Dating Site According to Your Personality

Read more

Dating Apps or Dating Sites, Which Is Right For You?

Read more
eharmony membership plans & prices

How Much Does eharmony Cost?

Read more

The Ultimate Guide to Boosting Your Zoosk Dating Profile

Read more