October 20th, 2011 by Elizabeth Marie

What To Wear On A First Date

I can’t tell you how many times I’ve stood in front of my closet, clothes thrown everywhere, debating what I should wear on a first date.  I want to look pretty (duh), a little bit sexy but not too sexy, classy, and yet portray my own sense of style.  It’s exhausting!

The key is to keep it simple. A first date is not the time to out try a crazy new trend that you’ve never worn before.  If you’re uncomfortable with what you’re wearing, you’ll look like it, and your confidence will suffer.  If you’re anything like me, your outfit choices can set the tone for your whole day!  Another thing to consider is where you’re going on your date.  A cocktail dress won’t work on a hike, just like a casual pair of jeans would be inappropriate for a nice restaurant.  Rather than risk being improperly dressed, make sure you ask your date what the plans are. A girl has got to know!My favorite things to wear on first dates might seem boring, but they work.  I know I look good in them, I feel good, and I’m comfortable. Winning! Here are a few examples.

For a casual lunch date- A chic,casual dress, cute wedges, stylish accessories and laid back yet polished hair.  See how the dress is sexy but not slutty? Just like you! :) Image via

For A Dinner Date-The little black dress is legendary for a reason!  It’s flattering, classy and chic.  Again-sexy, not slutty! That is your mantra! I would pair this little number with a bright clutch, curled hair and a smile. Men can’t resist…

The Quick Coffee Date-You know, when you’ve just started talking to a guy online and you want to meet him in person and make sure he’s not a serial killer?  The date is short and sweet, and showing up dressed to the nines would be silly.  You don’t want to look sloppy though, so it’s important to be casual while remaining put together.  Rachel Bilson does this exceptionally well. Her jeans are tailored and her outfits are well thought out, yet totally relaxed and effortless. Image via

Gentleman, you’re up next!


Liz is We Love Dates social media manager. A former marketing account executive in the fashion industry, a bad breakup spurred Liz to start her first blog 5 years ago and she has been happily over-sharing with anyone who will read ever since. Obsessed with all things dating, love and tech, Liz has been referred to as the brunette Carrie Bradshaw on more than one occasion. If it's a day that ends in "Y", most likely you will find Liz furiously typing away on her laptop with a huge espresso nearby. Or two. Follow her every thought on Twitter and Google+.

6 Responses to “What To Wear On A First Date”

  1. October 20, 2011 at 10:54 am, my honest answer said:

    So true about not wearing ‘the latest trend’. I’m just not cool enough, and always end up feeling really uncomfortable tugging at the ridiculous fringing / massive shoulderpads / other short-lived fad. Not a good look on a date, however on trend you are.

    And men never know what’s fashionable anyway. They just know what sexy looks like, and what slutty looks like! It’s a fine line, I think you’ve trodden it perfectly with these recommendations. Particularly love the day dress BTW.

  2. October 24, 2011 at 6:10 am, Sydney Escort said:

    I love the little black dress! It suits any occasion. And, I agree that you should stick with the clothes you are more comfortable with on your first date. :)

  3. October 30, 2011 at 5:25 pm, YouMeetMe said:

    Your dress has to be simple, decent, classic, stylish, and it also potray your inner as well as outer personality

    • October 31, 2011 at 1:03 am, Liz said:

      Completely agree! Thanks for your comment!

  4. June 04, 2012 at 3:38 pm, Rachel said:

    I always wear sexy jeans and a nice top for a first date. I figure if a guy doesn’t like me in jeans, he isn’t going to like me any which way, so I prefer to save my smarter attire for a future date :)

  5. December 10, 2012 at 5:49 am, anniesmith018 said:

    Excellent Post!Thanks a lot for sharing this useful information.

Follow Us

Keep up-to-date on the latest relationship advice by following us on social media websites:

Our Sites

Niche sites specifically dedicated to finding you your soulmate

Free Ebook

Receive a bi-weekly recap, with exclusive content & offers just for subscribers!