What Women Should Wear on a First Senior Date

If you’re a senior lady and you’ve got a first date scheduled, a nagging thought you probably have immediately after accepting the gentleman’s invitation is, “What on earth am I going to wear?!”

Have no fear. That’s what I’m here to do: help you with all things related to senior dating, including your wardrobe. Read on to learn more about what I, as a professional senior dating coach, recommend you wear on a first date to make you feel confident and make the occasion really special. It doesn’t matter if you met him online or through friends, and it doesn’t matter if this is your first or 30th date in months. These tips apply to everyone.

First, think of the tone you want to set for a senior first date. It’s probably romance, right? Senior men and women tend to prefer a casual first date so they feel comfortable sharing details about themselves. That means you two will probably select a venue like a coffee shop, cafe, or park.

However, you don’t want your outfit to be so casual that the gentleman thinks this is just a friendly outing. When it comes to your image, you want to emphasize romance as a single senior lady on a first date. You want your senior date to leave daydreaming about you as his potential leading lady — not his new buddy. He’s got enough of those.

To emphasize romance on a date, you want to accentuate your feminine body, so I recommend to my midlife dating coaching clients that they wear a dress or skirt, and that’s what I recommend to you, too. Wearing pants or shorts may signal that you consider this just a friendly day date. You don’t want to be put into the friend zone or have him think you’re putting him into the friend zone.

However, a flowy skirt is whimsical, and you can play with it while you talk to him. If you choose to wear a dress, a floral dress looks great on practically everyone. Floral dresses come in so many styles that you don’t have to wear them just during the warmer months.

The color of your first date outfit should also put a spotlight on romance. What colors do that? Reds, pinks, salmon, dusty rose, coral, and burgundy. All these colors highlight your sexuality and sensuality in a subtle and graceful way.

Wearing shades of reds and pinks brings out your sensual side and signals to your date that this is a romantic outing.

You want to be careful with solid bright red dresses, though. Sometimes it’s too much for a casual day date, so you’ll want to wear red highlights instead. Maybe try a red blouse with a black skirt, a red scarf with a white top, or just red lipstick and red nails. Hints of red are fine. On the first date, I suggest you highlight romance, not a straight line to the bedroom.

If you’re worried about coming off as too sexy with any kind of red in your outfit, you may feel more comfortable sticking to the more subtle colors I mentioned above, which are both flattering and romantic. It also depends on the time of year. Pastel pinks look great in the springtime, while burgundy is a fantastic color to wear during the winter months.

If it’s been awhile since you’ve been out on a date (or even gone out for a nice evening with friends), it may be time to go shopping. I’m sure you love hearing that! It’s true, though. This is a special occasion, and you deserve to treat yourself. It’ll give you a self-esteem boost for your date.

Even if you two decide to go for a coffee or lunch date, you want to impress him with how you dress. Go to that unique boutique in your town, and try on a few dresses and skirts that you normally wouldn’t wear. It can be exciting, and you may come across a new style that will turn heads. If you don’t find anything, stick to the styles that you know and are comfortable with. The point is to just put in some effort.

Or, if you prefer shopping online, browse for a date-worthy dress on your phone or laptop. There are plenty of online shops that are dedicated to serving midlife women.

You don’t have to make this a major expense either. I’ve found plenty of affordable dresses, skirts, and tops in town and online for about $30 each. Just dedicate some time to it. Maybe ask your friends for some advice, and bring them along on the shopping adventure to get their opinion.

Let’s say you’re still working and are heading to meet your date at the wine bar right from the office. You can jazz up your work attire by wearing some conversation-starting accessories.

Scarfs, earrings, rings, headbands, necklaces — choose a statement piece that’ll catch his eye and get the conversation going.

I’m thinking big hoop earrings, a colorful ring, your mother’s pearl necklace, or a romantic shawl that you got on your trip to India. Get creative! Dig through your drawers, or borrow from a friend.

As a woman over 50, you probably know by now that many single men have trouble making small talk and breaking the ice on a first date. Wearing a conversation-starter accessory assists him in making appropriate and engaging small talk without it leading into the pitfalls of oversharing.

When it comes to picking an outfit for a first date, you don’t want to try too hard. Follow your instincts. Ask your friends for advice. Keep your accessories casual and your outfit exciting, or keep your outfit casual and your accessories exciting.

When you dress to emphasize romance and authentically accentuate your femininity on a first senior date, you feel fantastic, attractive, and your best. When you do that, you greatly improve your enjoyment of the date.

Most importantly, think confidently and smile. Those two things go a long way.

I’m sure you’ll look nice, and your date will be so smitten that he won’t be able to wait to ask you for a second date. After all, who wouldn’t want to spend more time with an alluring and engaging senior woman such as yourself?