Stylist Advice- How To Look Hot On A First Date but not too hot that you come off the wrong way

DIANE von FURSTENBERG Dress - Aurora Three-Quarter Sleeve Dress at Bloomingdale's

We sometimes get so confused as to what to wear on a first date. Through the years, I’ve been asked all sorts of dress questions, particulary from women re-entering the dating scene.

In this week’s 15th Anniversary post, let’s reflect back to what a lovely lady over 40 should consider to wear on a first date.  Oh, as far as her date, I have some advice for him here too. S.H.

>> MORE: Dating Dress Tips

q2Dear Sharon: I’m in my early forties and still find dressing to look hot for a first date to be mind-boggling.

I never thought that I would actually be one for Internet dating, but here I am meeting a guy for coffee or a drink for the first time and don’t want to give off the wrong impression or come off as stuffy.

FocusOnStyle.com, online since 1999!What can I wear for an after work blind date so I look hot but not TOO hot or like I’m glued to the office?  (Suzy via via fashion advice)

>>MORE: Stylist Advice and Figure Out What to Wear

A:

What’s your favorite outfit that makes you feel great about yourself? It’s really that simple when it comes to dressing for a first date.

Same Diane von Furstenberg  Aurora Mini Dress in Pink at Shopbop- Chic with effortless appeal, this DVF dress has a feminine, figure-skimming silhouette with darts that shape the bodice and a split V neckline that shows off the collarbones.
Same Diane von Furstenberg Aurora Mini Dress in Pink at Shopbop- Chic with effortless appeal, this DVF dress has a feminine, figure-skimming silhouette with darts that shape the bodice and a split V neckline that shows off the collarbones.

When it comes to dressing for a date, we can have a tendency to over analyze what the other person would think of us rather than focus on what makes us feel good. And just like a dress, a good relationship is with someone who makes you feel great about YOU and soar.

Most guys, unless they are in the fashion business, don’t know if you’re wearing Prada or Plucked From A Resale Shop. What they do notice, is the confidence and individuality that you evoke which makes you ever so captivating.

I would avoid anything that has you fidgeting, like a too short skirt that rides up when you sit or a low neckline that has too much”spillage” when you lean on a table.

Since you’re going on an after work date, I wouldn’t worry too much about wearing something provocative unless that’s your work outfit and a whole OTHER story.

Conversely, I would not wear anything too covered up as that sets up a “closed” vibe unless it is the dead of winter.

Show a bit of chic skin by way of 3/4 sleeves, cigarette pants with sexy shoes (not clodhoppers no matter how trendy), a fitted but not clingy figure-flattering dress, a V-neck that highlights your collarbone but not your cleavage, a fitted jacket with a drapy blouse underneath and leg-lengthening pants.

Get the picture with these work to date looks:

 

Add some glam to your office day look by perhaps switching out to non-distracting jewelry that doesn’t take away from your smile, a fab pair of heels, and maybe a dramatic, more smokey eye. Then go have fun and be confident in your own unique fabulousness. It’s only a date.

Have you ever been on an Internet date? Tell us your stories, good and bad, in the comments below. We are all ears…

JUST ASK: Do you need some quick stylist help to amp up your style?  Email us for Fashion Advice.

Lead photo: DIANE von FURSTENBERG Dress – Aurora Three-Quarter Sleeve Dress at Bloomingdale’s; also available at Shopbop and Sak’s

Originally Published on: Aug 23, 2012

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