Dating can be nerve-racking enough, but add in the anxiety of planning your first few date night outfits and the anxiety increases tenfold! I turned to celebrity stylist Sandy Hapoienu to find out what the best possible date night outfits would be for a first meet and greet, meeting at a trendy bar, a dinner date and a night at the gala.  I had the pleasure of working with the talented Sandy Hapoienu at Bloomingdales in White Plains NY for the shoot, and Sandy chose her top picks for the following date nights.

Meet and Greet Outfit: Over the knee suede boots, long cashmere sweater paired with chunky necklace and camisole.

Sandy, why does this look work?

This look is perfect for a “meet and greet” coffee date because it’s casual, yet it looks pulled together and sexy. You only get one chance to make a first impression, so make it memorable. The cashmere sweater is the key piece. It is not chunky so it is figure flattering and soft to the touch. Different boots may have worked here but the over the knee boot is right on trend and adds some sex appeal. The statement necklace finishes the look for an overall polished look.

Drinks at a trendy bar: Tunic embellished top over leggings—very Coco.

No need to accessorize here as tops and dresses with built in jewelry are a great time saver.

Should you pair this with any accessories?

Wear it under a blazer for work so when the day is done you are ready for happy hour. This top has a playful tone and says you are ready to have some laughs and kick up your heels.

Dinner, 3rd date: Black wrap dress shoulder detail.

Why does this dress work so well?

This LBD (little black dress) has a lot going for it. First, it’s a wrap dress. Therefore it emphasizes Kris’s narrow mid section and curves without making her look vampy. The shoulder detail takes the dress from ordinary to fabulous while also adding to the hourglass shape.

The Gala: Opera green one shoulder faux wrap with long sexy slit.

How does this dress accentuate body tone?

I like this dress for many reasons. First, the color was complementary with her skin tone. Second, the dress creates a waist accentuating curves. Finally, the draped look created a conservative glamour, fitting for these occasions.

What are some style trends for the fall?

Please keep in mind that fit and portion are key to real style. If you want to update your wardrobe, here are a few of my favorites this season.

Camel and olive were the 2 strongest colors on the runway.

Leather and lace are strong in all garments from T-shirts to dresses. I actually love them together to show a little edginess and foster femininity at the same time.

Another strong trend is the sheer button up blouse; it’s prim but provocative at the same time. Pair it up with elements of menswear for contrast and a touch of excitement.

What are some of the most flattering styles to wear for the upcoming holiday season?

I am a strong believer in dressing for your body type. Fit is your number one accessory. That being said every girl needs something sparkly. Sparkle comes in all shapes and forms this season from gilded to sequins and from headbands to shoes. Stock up on belts and create an hourglass shape. Try belting everything from coats to dresses and see what it does for your shapes.

What are some of the biggest style mistakes women often make on dates?

Most women feel if they wear oversized clothes, they will hide a multitude of flaws, but what it actually does is create volume and draws attention to a larger silhouette.

Don’t wear clothes that are too tight as this can be as lethal as oversized clothes. My suggestion is that you buy for the largest part of your body and find yourself a good tailor.

Mom jeans—don’t wear them on a date. Do yourself a favor and get rid of them today. Contrary to popular belief, you don’t have to spend a lot of money for a cool pair of jeans.

Heavy perfume can be a big turn off.

What are your top 5 tips for women to always look glam and have great style on dates?

High-heels: Add sex appeal, to your jeans or dresses, as they look good and make you feel good too.

Make-up:  I love make-up…but there is day appropriate make-up and night time make up. Make sure your make-up is not too much or too little.

Look in the mirror.

Accessories: You can never have too many shoes or handbags—need I say more.

Mints: Always be prepared!

Top 5 tips for mens style on dates?

Listen up guys—casual does not mean sloppy. I think fit is just as important for the men as for the ladies.

You are what you wear, and clothes create an image. What do your clothes say about you? Do they say loyal and responsible, or I just don’t care… Look like you gave your outfit some thought and, at the very least, have a cohesive style and a wrinkle free look.

Shave: I am sure the lady is well groomed. If you don’t look like you are, she may be turned off at first sight.

Here are some don’ts: Please stay away from the following:

White socks, oversized clothes, sagging pants, sneakers and heavy cologne.

About Sandy Hapoienu:

Sandy Hapoienu is a New York based stylist. Her company “Styling Session” has worked with celebrities, the runways and editorial shoots. She also covers personal shopping, and corporate shopping for professional presence, closet edits and gift certificates. Sandy is also a fashion and market writer/editor. She has a strong presence as a fashion and home trend expert in print and web media with hundreds of bylines to her name. In addition, as a permanent fixture at fashion week, major trade shows and affiliated with global trend organizations, she is always looking for the next hot trend. If you have any questions, feel free to contact her at

*Clothes were provided by Bloomingdales White Plains, New York. Special thanks to Bloomingdales in White Plains, and to Meryl Lefkowitz and Sandy Hapoienu for donating their time to JDate for the shoot.

About the Author
Kristen Ruby is the President & Founder of Ruby Media Group, a Social Media Marketing, Public Relations & Personal Branding Agency. Follow Kris on Twitter @sparklingruby or via her blog.
  1. Sandy Hapoienu did such a great job with this shoot! I love the outfits she chose- especially the green dress for the gala- magnificent work Sandy! Thank you again to Bloomingdales and Meryl Lefkowtiz, and everyone at NARS for makeup. What a great shoot! I love all of the outfits and your tips are spot on!

  2. Looking your best never hurts…………….being obsessive about it does. Most of all, be yourself.

  3. Love this article! Especially the great outfits. Nice work! Style is important!

  4. How about some ideas for women over 50. Even though I am fit and love to wear modern clothing, I cannot picture myself wearing sweade boots over the knee or leggings.
    I would appreciate if you give us some classy trendy ideas!!

  5. “You are what you wear,” and “you are what you eat”.

    To avoid multiple-personality disorder or schizophrenia, you must wear suede when eating venison, you must wear pure cotton when roasting marshmellows, you must wear chaffron when you eat your chauffeur. When it’s his turn, you must have the chaffroff. You can’t eat corn flakes without listening to corny jokes on the radio, and you can’t drink Coca Cola without wearing an Uncle Sam get-up.

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