Whether you’re single, married, or newly divorced, you go out on dates. If you’ve been married thirty years your dates might be going to Costco with your hubby and catching an In-and-Out Burger afterward, but it’s still a daytime date (at least I consider them dates!).

Whatever constitutes a date in your mind, a common challenge my clients face is creating outfits for any special occasion or date night because they feel like they just don’t have date night quality clothes in their closets. The theme I hear from women over 50 who are back in the dating scene is CONFUSION. These are mature, successful, very capable women in every aspect of their lives, but dating outfits bring on all the old self-doubts. Let’s face it, we’re not twenty anymore. The question of how much skin to show on a first date is not even relevant at this point. The question is how do you find clothes that cover the skin you WANT covered up, while still looking vibrant, interesting, and perhaps flirty? That’s the crux of the matter!

If you’re new to the dating scene, you don’t want to be like one of my clients who called me in a panic before her first date (who later became her husband). She was literally having an anxiety attack about what she was going to wear. When I drove to her house, her bedroom looked like it was hit by a tornado. I finally got her to calm down and talk to me about what she wanted to express with her outfit that night, where she was going on the date, and what pieces in her closet made her feel the most comfortable and beautiful – the most like herself. It took no time at all to dig out of the pile a beautiful, sophisticated and sexy outfit for her first date.

When I look in a woman’s closet, I can identify the issue right away. Most of the time, there are plenty of special pieces she could wear on a date, but she doesn’t see the possibilities because her dressier clothes are either in a different closet or tucked way in the back of her closet.

Let’s face it, the term “dressy clothes” has changed its meaning. Nowadays, dressing up means wearing jeans that don’t have holes poked in the knees! For women over 50, we still remember the good old days of wearing a pretty dress and high heels for a special occasion. The reality is, whatever you wear is acceptable, it’s more a matter of FEELING DRESSED UP and special when you go out on a date.

So, how do you take your current wardrobe and find outfits that make you feel attractive, comfortable, and special at the same time?

Here are my tips for a date night outfit:

Tip #1: Shop Your Closet

You don’t always need to go shopping in order to have an amazing date night outfit. Go shopping in your own closet. The first step is to see everything in your closet as POTENTIAL.

Look for ways that your existing pieces can play and work together that you might not have tried before. For example, throw a gorgeous scarf around your neck with a Covered Perfectly (I’m getting my 20% stylist discount I can share with you soon!) top and dark pants. Or, combine a short dress with a pair of leggings and booties or sexy sandals. Set aside some time to mix and match, and even invite your girlfriends over for a fashion show.

You could also take a blazer (from a suit you never wear anymore) and spruce it up. Pair the blazer with a loose-fitting, long, silk blouse and wear skinny or ankle length pants. The feel of a soft, silky top against your skin will make you feel alluring and comfortable.

Add sparkling accessories, such as bronze or silver shoes, crystal earrings, or that huge ring you’ve been saving. SPARKLE! Simply adding a pin or brooch to the lapel of your suit jacket will completely change how it feels and looks on you.

Let the items work together. Re-purpose things. Experiment. Play in your closet! This process is a lot of fun when you approach it with curiosity and a sense of play.

Tip #2: Wear Your Best Colors

Color is energy. Color can change your mood. Why not use color to create a happy, relaxed, fun mood for your date?

Your best colors will help you look young, healthy, vibrant and interesting! Here are some color combination suggestions:

  • If you’re a GOLD (spring), wear a coral top with a teal blue pencil skirt and top with a camel trench coat, shiny gold bracelet and heart-shaped necklace.
  • If you’re a SILVER (winter), wear a simple black dress or 2-pc black sleeveless tunic and black pant, bold silver jewelry and a short jacket in a jewel-tone color.
  • If you’re a PLATINUM (summer), wear a mauve, pleated maxi skirt with a gray, lightweight sweater, velvet jacket and wrap a gorgeous scarf around your neck for a sophisticated, soft look.
  • A COPPER (autumn) can rock her look with a long suede skirt, a silky animal print blouse, dark denim jacket and chunky necklace to pull it all together.

I recommend wearing the color that gets you compliments every time you wear it. People notice color first thing. You want to meet your date with sparkling eyes and radiant skin, and the right colors will do it!

Tip #3: Pick Your Favorite Piece and Build An Outfit Around It

What is your absolute favorite piece of clothing or accessory to wear? If it’s a pair of shoes, build an outfit around it. If your favorite piece is a vintage jacket, choose a top that looks great underneath, a pair of pants or skirt, and vintage accessories. Or, in my case, below, I’m wearing a favorite silk top that makes me feel flirty every time! The point is to start with one piece and build around it. You don’t have to always start with a top or bottom – it can be a favorite necklace or pair of shoes.


Tip #4: Go Flowy and Silky

What could be sexier than wearing your silky pajamas out on a date? Well, I’m kidding…sorta. Street lingerie is so acceptable now that you can basically be as comfortable as you want.

For a warm summer evening, wear wide-legged, cropped pants with a loose-fitting silk or rayon tunic top. Throw on a couple layers of long necklaces, some bangle earrings, and low-slung kitten heel sandals, and you’re set! Bring a pashmina to wrap around your shoulders when it gets chilly.

Tip #5: Dress Your Personality So You Feel Like Yourself

The quickest way to relax on a date (especially if it’s a FIRST DATE) is to wear clothes that make you feel like YOU. For example, I don’t normally wear lace. Although I admire it on others, it just doesn’t feel like me. I think if I wore it on a date I’d feel like someone else! The whole point of dating is to get to know someone and allow him/her to get to know you.

Put an outfit together that is authentic and the best form of YOU. Wear something that is comfortable and expresses your personality. The key is to look approachable and low-key. If you love wearing romantic, flowy styles, wear a cowl neck silk blouse over cigarette pants and a long, flowy cardigan. Or if you like a simpler style, wear a lightweight sweater in a beautiful color (matching your eyes) over a satin tank with skinny jeans. Add strappy sandals or a cute platform shoe, whatever is easy to walk in. Add a bracelet and a handbag in a pop of color. Think comfort. Wearing clothes that express who you are inside is a powerful way to step fully into yourself. Your date will receive your confident messages loud and clear.


If you’d like more personalized style tips for date night or a special occasion outfit, be sure to take advantage of my
FREE 30-MINUTE STYLE CALL WITH LINDA. Click here to get on my calendar.