Plus other general tips and advice for mature dating
“The way you dress is a silent language that speaks volumes.”
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Every time I give style advice, I repeat the same statement confidence is sexy. This notion applies to how you feel when you are getting ready for a first date. If you don’t feel confident and comfortable with whichever outfit you have selected to wear on that first date, it’s going to show.
I must admit that I searched online for what to wear on a first day more than once. Although we are mature women and supposedly “experts” on dating by now (at least some of us), that doesn’t mean that we don’t want to look our best. Whether you’ve finally taken the plunge and agreed to that first date or you are a seasoned pro and have been on the dating circuit for a few years, figuring out what to wear can send even the most put-together of women into a spin.
We all know that first impressions are paramount. Whether it’s a blind date (you two met on a dating app) or you are having a first date with someone you have already met in person, you need to look great on that first date.
In my opinion, there are three key elements to look for: elegance, sexiness, and comfort. If you achieve all three, you are way on your way to success.
In this peace, I will be providing general advice to consider when you are ready to go on a first date. The rest of the post will focus on style tips, advice on what not to wear, and suggestions on what type of clothes or outfits work best to look fabulous on your first day with a potential partner.
Before getting into style advice, here is some essential general advice about mature dating, regardless of whether you are dating again after divorce or you have been dating for a while with little or no success.
General Tips for mature dating
- Be the best version of you
It’s important to be true to who you are, but also want to put your best foot forward, so dress to showcase the best version of you.
No matter what style personality you are (sexy, bohemian, preppy), be sure to look polished, well-groomed, feminine, and a little sexy, too.
- Communicate well
Dating again at 50 or over can be nerve-wracking if you have not dated in a while. The first date’s success depends on how well you connect, and that depends on how well you communicate.
Communication is a combination of what you say, what you don’t say, how you listen, and what your habits and body language transmit. Communication is the foundation; it helps build chemistry. The basic rules of communication are straightforward.
Before your date, think about what to talk about or what to say or not say. You want topics that interest both of you that are respectful and that help you get to know each other.
Communication don’ts:
- Badmouthing an ex or using any derogatory terms when referring to him.
- Bragging about a job and how well you are doing.
- Playing the victim.
- You are giving someone a novel about your life instead of asking your date questions. In dating, listening is as much or more important than talking.
Communication Dos:
- Say things that give your date a sense of what you do regularly.
- If you talk about work, think about what this listener would like to know about you. Are you disciplined? Hardworking? Say something that gives your date an idea of your work and shows the good sides of your character.
- Make the other person feel important, unique, and like he matters. Listen and be interested in what they have to say. You can never be wrong treating someone with this kind of respect.
- Level with your date. Don’t be afraid to be upfront about what you want.
- Feel good about yourself, be confident.
One of the biggest secrets of a great date is feeling good about yourself. Remember that if you like yourself, he most likely likes you, too.
If a woman dislikes herself, it is impossible to feel or look confident. If this is your case, I suggest you work on this issue before anything else. This blog offers valuable information about self-love and self-care that can help you achieve that elusive self-confidence.
- Relax.
First dates are meant for playful conversations, fancy cocktail drinks, and getting to know someone new over a nice meal or shared dessert.
That first date might be a dating app pick, a friend’s fix up or a “let’s grab a bite to eat” from a high school ex you friended on Facebook. Whatever the source, it’s an audition. At the very least, you’ll get some dating practice and perhaps lots of fun conversation. At most, you may gain a blazing romance. And if it doesn’t work, so what? You will go to the next one. Believe me; there is always a next one.
And now it’s time to focus on looking beautiful and confident by picking the perfect outfit. First dates give you the chance to dress up and put on an outfit that makes you feel and look like a million dollars. To help you get inspired, I will give you style advice and outfit ideas to make you feel gorgeous.
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But first, there is a fine balance between looking attractive, elegant, and interesting versus looking inappropriate, like you tried too hard or you are too high maintenance. You want your clothes to help communicate who you are on a first date, not give the wrong impression. Knowing what not to wear is as important as knowing what to wear.
What NOT to wear on a first date
- Super high heels that you can’t walk in
- Anything that shows too much skin
- A brand new outfit or new shoes
- Anything that is out of character or you wouldn’t wear normally
- Anything that doesn’t fit well. At all costs, avoid skin-tight clothing
- Athletic wear
- Too much makeup
- Bare face
- Stiff hair
- Dramatic silhouettes
- Any new trends you haven’t fully mastered
- Turtlenecks
- Plaid shirts
- Baggy tops
- Clunky shoes
- Rough fabrics
- Muted, sad colors like beige or industrial blue
- Outfits that cover you head to toe
Style tips to succeed on a first date
The 3 golden rules:
-Stick to pieces that make you feel great and are comfortable. You want to focus on your date rather than nervously tugging at a hemline or sleeve.
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-Pay attention to proportion. For instance, if you show off your legs, keep your chest covered with a high neck design. Conversely, if you show cleavage, balance the proportion with a nice tailored trouser or an a-line skirt.
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-Be fearless with fashion. Clothes are not about fitting into the latest trend but finding what works for your body, the occasion, and how they reflect your personality. It’s time to be fearless with fashion, and bold is choosing what’s best for you.
Essential tips for style over 50
- Classic is always classy
A good starting point for a first date is to find a happy medium between casual and classy.
- Wear your hair down. Luscious hair moves. This is not the time to pull your hair back in a tight ponytail or wear a hat.
- Prioritize tops and accessories. Be high visibility from the waist up. It’s your top half that’s on show for 90% of the time. Think color, neckline, sleeve length, and jewelry.
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- Show off your best features. Wear a statement belt if you have a defined waist, show off your toned legs or arms, whichever part of your anatomy you like the best.
- Wear color! Color is an overlooked but rather easy way to boost your confidence, look, and energy.
- Don’t look like you are trying too hard. Jeans work everywhere on everyone, so have your favorites on call. You will never go wrong with those.
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- Comfort is key. An additional golden rule for fashion over 50 is comfort. You shouldn’t sacrifice style for comfort, but without comfort, you can’t be stylish.
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- Have some edge. Boring clothes are well? Boring. Add something a little unexpected or wild-snakeskin booties, leather leggings, bold glasses, or smoky eye makeup.
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- Make an effort. It’s disrespectful for the other person to show up on a date looking like crap.
- Look like you. It’s ok to use filters to tweak online photos, soften lines, or brighten skin. However, at 50, your weight, hair, and looks do change. Don’t apologize or explain; just show up and be yourself, looking your best.
- Find your fit. Try out new looks and styles, and decide what works for you and your body.
- Elegance is attitude. Ask Audrey Hepburn or Coco Chanel. True beauty and elegance start on the inside and work their way out from there.
The ideal outfit is both well-fitted and comfortable, in a cut and material that flatters you. You can dress like a lady and present yourself well. However, It’s also essential that you work on your attitude towards yourself. Being comfortable on your own skin is the best look on anybody.
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Best first date outfit ideas if you are 50 or over
- A simple fitted knee-length sheath dress is a foolproof option. Accessorize with a statement necklace or drop earrings and classic heel pumps or heeled sandals.
- Dark-wash jeans paired with a colorful or printed blazer. Add a simple plain blouse or shirt underneath and team with ballet pumps (or heeled booties) and a structured bag.
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- Squareneck knit dress with a trench coat, heeled boots, statement earrings, and shoulder bag.
- Straight leg jeans, silk blouse, hoops, leather shoulder bag, and neutral low-heeled mule (daytime) or red heels (evening).
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- Little black dress. The ultimate classic, every woman looks great in a LBD. Make sure you accessorize it well.
Shop Dress the Population Catalina Dress
Remember, you want to look cute and pulled-together, but also feminine and sophisticated.
The Takeaway
Don’t try to dress up as someone you are not. Be your authentic, genuine self and have fun with it! This is particularly important on the first few dates because you want your date to see you for who you are, not a contrived version of yourself.
At the end of the day, fashion for women over 50 is about feeling fabulous and healthy-mentally, emotionally, and physically. Great style is about feeling excellent. Make sure you take care of yourself, respect yourself, and allow your light to shine bright. There is nothing more attractive than confidence and character.