We’ve all been there. First date with a person you’re really interested in. You have the perfect date, perfect place, but now, you need to find the perfect outfit. Here is where the tough part comes in. Should you be sexy, cute, casual, sporty, or all of those rolled up into one. How do you feel cool, comfortable, and at the same time look your most appealing?

It’s easy to say “be yourself,” but sometimes that doesn’t work on a date (especially a new date). For example, I love nothing more than wearing oversized kaftans during the summer….but, I think I would save that part of myself for a few dates in! While I encourage my clients to dress for themselves, date night is an occasion where you should keep in mind what your date will like (and not your fashion-crazed friends). Of course, your date should be interested in what’s on the inside, but it never hurts to keep the outside sexy.

Here are some of my picks for date night tops that will make you look and feel great. I hope you have great dates this fall!

Quick Tip: It never hurts to toss a spare tank or t-shirt in your bag to avoid the much dreaded “walk of shame” the morning after!

The Row: Kristi Top
This LBT is timeless, slimming and made from soft fine knit jersey (i.e. comfortable) while accentuating a gorgeous shoulder and neckline.

The Row - Kristi

Roksanda: Ranae Sleeveless Peplum Top
I must show this top paired with slim black pants and heels to do it justice! This flattering look is sexy and cool yet still manages to appear feminine and sophisticated.

Roksanda - Ranae top


Rosie Assoulin: Off-The-Shoulder Silk-Gazar Top
This top is very “of the moment” and might just be the perfect shade of red! Remember, you’ll likely be sitting at a table for dinner or drinks, so plan your outfit accordingly. That dress that looks amazing when you’re standing can bunch up in unflattering ways when you’re sitting. This off the shoulder shirt looks amazing in any position and has a gorgeous neckline that will enthrall your date. It is best paired with a wide leg denim pant and heel or a narrow black pant.

Rosie Assoulin top


Isabel Marant: Cotton-jersey embroidered top
Here is another LBT that is easy and feminine. The cut is great – cap sleeves, plenty of décolletage reveal and side-hem slits so the shirt will sit nicely on the hips. The beautiful embroidery and beadwork make it interesting in a subtle way.

Isabel Marant top

REDValentino: Macramé-lace top
This lace and macramé top with a sheer neckline and sleeves has a romantic and delicate feel. It pairs perfectly with denim for a more casual date.


Oscar De La Renta: Daisy-print lace-trimmed top
This top is a perfect transition from work to date. Slip off your blazer to unveil a sleeveless daisy print shirt with a sheer floral-lace front that leaves a little for the imagination. This shirt gives off a sexy, mysterious vibe that is perfect for a dinner date and can transition to cocktails after dinner.

Oscar De La Renta Daisy top


Last bits of advice for choosing a date night top:

  • Plan ahead.
  • Try different tops with a variety of bottoms – dark denim, cigarette pants, pencil skirts.
  • Make sure you feel confident in it.
  • Don’t wear white if you’re going for dinner that splatters (pasta, etc.)
  • Wear it with a smile.

Visit my Date Top Pinterst page for more date night top ideas.