What to Wear On a First Date

What to wear on a first date


Written by stylist Gayle Elizabeth Rich


What to wear every day can be challenging. Now add on the pressure of choosing an outfit for a first date!  One can become anxious with indecision, and the fear factor rises.

Before we get to your wardrobe choices, there is one thing you need to wear first that no designer can make for you – it’s called CONFIDENCE. Practice on a daily basis, whether you are dating or not, some positive self-talk and self-soothing. It is good to approach dating as if meeting a potential friend, that way there is less stress put on the occasion. Leave romantic possibilities outside your vision.  Be true to your real self while dating and allow your clothing choices to reflect that.

Generally speaking, your outfit should convey an effortless and comfortable you. Your choices should be flattering and represent your best self.  This is who you are.  This is your style personality.  Of course, this requires knowing yourself, your style, and some careful planning for the event.  Anyone can just grab a tee shirt and jeans, but if you want to leave a more lasting impression on your date, put some thought into what you wear. Don’t know where to start? No worries, keep on reading and let me stir your imagination by providing some styling choices for possible first date scenarios.

Remember that the clothing you choose is the way you want the world to see who you are.  Use this advice by showing your date who you are, and also by reaffirming it to yourself.  Honor your authentic beautiful self.

Please keep in mind that these are general recommendations that might not suit any individual body type and personality.


Café Dating


Meeting at a café is a perfect daytime first date meeting place. A daytime date contains less pressure, and is emotionally safer all around.  The following are some wardrobe choices I would recommend:

—From Anthropologie the Gianna” printed wrap top worn with white jeans for spring/summer.

What to wear on a first date

—The 3.1Phillip Lim short sleeve ruffle top worn with stylish jogger pants available at Saks Fifth Avenue.

What to wear on a first date

  

Brunch Dating


A brunch first date welcomes a pretty blouse and slacks, a casual dress, or a soft jumpsuit.  Enjoy your food, your company, and the beautiful day that is ahead of you while looking gorgeously elegant and relaxed.

—A soft feminine choice from Rebecca Taylor is their Sweet Briar” jumpsuit
What to wear on a first date

—A more tailored classic jumpsuit choice comes from Intermix. The jumpsuit is called "Delia Chambray" by L'agence.  

What to wear on a first date

—From Moda Operandi, consider a fun Giza cigarette pants by SemSem in cobalt blue. It would look stunning with the J.O.A.ruffle sleeve top from Nordstrom.  This black blouse has a beautiful and subtle white star print.

What to wear on a first date

What to wear on a first date
 
—Or choose Alice& Olivia “Idalla Cold Shoulder” silk blouse from Saks Fifth Avenue to wear with a tapered pleated pant by Piazza Sempione in a soft eggplant tone. It is also available at Saks Fifth Avenue.

What to wear on a first date

What to wear on a first date



Walk in the Park Date


Some people like to approach their first date in a more casual and relaxed way like meeting for a walk in the park. This walk can continue to dinner later, who knows…

—A striped shirting tie back dress by Tibi is a perfect dress for a casual stroll in the park, which can work well at an outdoor cafe for appetizers later. You can accessorize with a light fun small bag such as Khokoh Thembi Bucket Bag available at Intermix. 
What to wear on a first date

What to wear on a first date

       
What to wear on a first date

What to wear on a first date

As for your choice of shoes, pick something that is comfortable to walk in and yet nice enough in case you decide to go to a restaurant later. Try Carrie Forbes Driss Slide from Club Monaco, or Loeffler Randall Rhinestone Studded Blush Suede Sandals from Intermix.   

What to wear on a first date

What to wear on a first date




Sports Game Date


Maybe you found out that you are both fans of the local sports team and would like your first date to be at the game. If you run out of discussion ideas you can always talk about the game. You can make a sports game first date memorable by wearing jeans in a fun color like the Rag& Bone mid-rise skinny jeans in red at Saks Fifth Avenue. With the jeans, wear a tee with some detailing like the Current/Elliott ruffle roadie tee in sugar.  Cute sneakers to add are the grey gingham print sneakers by Superga.  Both the tee and sneakers are available at Nordstrom.

What to wear on a first date

What to wear on a first date

What to wear on a first date




Boating Date


And for the adventurous ones, who dare to go on a first date into the depth of the sea. Very courageous. A boating first date requires some extra planning.  Be prepared for swimming and a casual meal out later.  An easy one piece swim suit in sky blue by STAUD, available at Net-a-Porter, can be worn under light color shorts, tee, and faded denim jacket and sneakers, all available at Anthropologie.  Be sure to take a beach bag, such as TRUSS Weekender large woven raffia-effect tote available at Net-a-Porter. To change later into an embroidered “cape blouse” by Hemant & Nandita, available at Saks Fifth Avenue, and add some sandals.

What to wear on a first date

What to wear on a first date

What to wear on a first date

What to wear on a first date



Dinner Date


Finally, the classic choice of a date night – dinner, where you can get to know each other over the dimmed light of candles and the soft sound of music in the background. A dinner first date should be elevated with a dress, or skirt and top combination.  Just make sure you don’t over do it with over the top jewelry, dramatic make-up, or cocktail attire.  Making choices that resonate loudly with ‘trying too hard’ (or not trying at all) makes a negative impression.

Two dinner first date choices I like are:

—The off-the-shoulder postcard print dress, sandals, and earrings from J. Crew…and instead of the sandals, another fun choice could be the Loeffler Randall Vera Heel, available at Rebecca Taylor.

What to wear on a first date

What to wear on a first date

—Another idea to inspire you is from Net-a-Porter. The grosgrain-trimmed printed cotton poplin skirt by Jason Wu worn with a mustard yellow cropped knitted sweater by DKNY. Simple ballet flats in black complete the look.

What to wear on a first date

What to wear on a first date


Remember to have fun choosing outfits for dating. Put your best self out there in the world; and the first step is to care about the clothing you choose to wear. Others in your peer group, work colleagues and friends, may not care about their wardrobe choices, but let yourself shine with confidence when you spend some time making a creative effort to step up your wardrobe. 

Now, go have fun and dress as who you want to be.


Gayle Elizabeth Rich is a stylist from the Seattle area. To learn more about her style philosophy read The Meaning of Being Stylist.







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