Over 50

Dating Confidence: How to Look and Feel Beautiful on a First Date

November 22, 2023

Dating Confidence: How to Look and Feel Beautiful on a First Date

After you have cleared the way for love to come into your life, the inevitable next step is dating. Dating either excites you or terrifies you. In either case, it’s what we have to do to test the waters and find out if there is chemistry. Let’s say you’ve just accepted a date with Mr. Potentially Dreamy. What are you going to wear? How much thought and preparation will you put toward your date outfit? I recommend putting enough thought into your outfit so you feel confident, comfortable, and a little flirty!

If you’re new to the dating scene, you do not want to be like one of my clients who called me in a panic before her first date with a man 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 we talked 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. It took no time at all to dig out of the pile a beautiful, sophisticated and sexy outfit for her date.

Here at 5 tips to dress confidently on a first date:

Tip #1 Start planning your date outfit as soon as you accept the invitation. I recommend you decide on an outfit several days in advance of your date because you may be missing a key piece or accessory that will pull it all together. Where is the date? Hiking? Movie? Dinner? Concert? Choose an appropriate outfit that makes you feel pretty, sexy, confident and comfortable. You will be so much calmer and happier knowing that every detail of your outfit is taken care of, so you can focus on feeling fresh instead of stress.

Tip #2 If you’re new to dating, get a style update. This could include hairstyle, eyeglasses (if you wear specs), or a makeup refresher with a professional consultant. It will renew and refresh you inside and out!

If you’re over forty, it’s important to find the most flattering hairstyle and hair color for your face. When I turned fifty I changed my look completely by cutting my hair super short in a pixie. It reflected a different side of my personality and I felt sassy! If you’ve chosen to go silver/gray, a trendy pixie or Bob cut looks sophisticated. If you don’t have time for the whole enchilada, just get a blow out before your date.

Update your makeup routine. Visit a department store or find a makeup consultant, and ask for a makeover. Try a smoky eye or a shimmery eye shadow! In general, warm colors suit warm complexions, and the same goes for cool colors. Makeup should be fun, not fussy or over-done. It’s not about changing your features or looking another age. It’s about wearing colors that complement your skin-tone and bring out your radiance!

Tip #3 Put an outfit together that is authentic and the best form of YOU. Wear something that is comfortable and expresses your personality while also looking approachable. If you love wearing romantic flowy styles, wear a cowl neck silk blouse over cigarette pants and a long flowy cardigan. If you prefer a simpler style, wear a lightweight sweater in a beautiful color (matching your eyes) over a satin tank top with skinny jeans. Add strappy sandals or a cute platform shoe that is easy to walk in. Add a bracelet and a handbag in a pop of color. Think comfort and style. Wearing clothes that express who you are inside is a powerful way to step fully into yourself. Your date will receive your confident message loud and clear.

Tip #4 Resist showing too much skin. This is advice I would give a woman of ANY age. Be mysterious; make him wonder what’s underneath. Here’s a style tip: if you are showing your legs in a dress or skirt (no shorter than an inch or two above your knees, pleeeze!), then cover your bodice and arms; if you show modest cleavage and arms, cover your legs (wear leggings, skirt with tights, tall boots, or pants). Don’t wear anything too revealing or uncomfortable that will distract you from your date experience.

Tip #5 Wear your best colors. This is SO important! Your colors will help you look healthy, vibrant and interesting! Here are some color combination suggestions in your color palette:

If you’re a GOLD (Spring), wear a coral cashmere sweater with a teal blue pencil skirt and top with a camel coat, shiny gold bracelet and heart-shaped necklace.
If you’re a SILVER (Winter), wear a simple black dress, bold silver jewelry and a short moto jacket in a jewel-tone color.
If you’re a PLATINUM (Summer), wear a mauve-colored, pleated maxi skirt with a short, soft gray sweater, dark gray or purple velvet jacket and wrap a gorgeous scarf around your neck for a sophisticated, soft look.
If you’re a COPPER (Autumn) you can rock your look with a dark suede skirt, tall boots, silky blouse, jean jacket and rich teal-colored scarf to pull it all together.

Written by Linda Waldon

Linda Waldon is a personal stylist living in Santa Fe, New Mexico. She offers virtual style consultations, closet cleanouts, and online style courses. Her recent book, Turn Your Closet Into Cash! is available on Amazon Kindle. If you want to know your color palette, take this free quiz, and learn more about how to mix and match colors with her self-guided color course, Color Me Stylish!

Big hugs ~