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What To Wear On A Date | CrunchyTales

Back In The Game: What To Wear On A Date After 50

6 min read

No matter what age you are or how many dates you’ve been on, dating can be daunting. Meeting with a potential partner after 50 can be even more complicated due to personal circumstances such as previous marriages, children, and having more responsibilities than when you were younger. Simply thinking about how long you’ve been ‘out of the game’ is enough to make you feel like you’re embarking on a hike through the wilderness unprepared. The good news is that at our age, we know exactly what we like and don’t like in a romantic partner and we tend not to waste our time with anyone that doesn’t meet what we are looking for.

Stepping up your game

Whether you’re new to dating at this age or have been at it for a while, there are a few things to keep in mind to make the process more fun. Going out with someone nowadays is completely unlike 20 or 30 years ago and as a result, the experience is vastly different. In recent years and especially due to the pandemic, online dating has taken over as a popular choice compared to traditional avenues. I am a firm believer in it and I am proof that it can work because at 53, I was lucky enough to find the love of my life this way.

However, even if styles and approaches to date might have been changed, wearing the right outfit on your first meeting is still important; knowing how to pull together a look that works for you can make a difference. Once you figure out a formula that works for you, having that “first date uniform” will give you the confidence boost you need.

Here are my top tips on how to look your best on a first date and beyond.

But first…pamper yourself!

Before even thinking about what to wear, it is a good idea to prep yourself and get in the right headspace. Take the time to get ready and enjoy looking and feeling good, for you! Pamper yourself and let it be a full experience. Whether you like to do face masks, paint your nails, take a walk or your favourite exercise class, do whatever it is that makes you feel happy. Starting with this step will help you put your best foot forward on your date because you’ll be much more relaxed and self-confident.

Effortlessly Chic

Give yourself enough time to pick out an outfit and try it on before your date. Use a full-length mirror to check yourself out from all angles to make sure what you chose fits well. The ultimate goal is selecting something that gives off an effortless vibe like you just threw on your outfit and left the house. Even though the last thing you want to do is to pick out an outfit at the last minute, stress yourself out and have to rush out the door feeling frazzled!

To emulate this effortless look, you’ll want to choose something that will make you feel put together and self-assured. Pick something that reflects you and your personality that you will feel great in. Being comfortable is key no matter what you are doing on the date because wearing something that you feel good in will help you to feel more at ease.

Keep it simple

Natural and minimal is always best for a first date. Choosing something simple yet understated does not have to be boring, though. You can’t go wrong with the classics; try to stay away from too many accessories or something too trendy that will create distractions and make you feel not like yourself. The last thing you want to be doing is fidgeting with your clothes.

Choose an outfit that will boost your self-esteem

There are certain colours that complement your complexion and really pop on you. Wear one that you have been complimented on in the past. Now is the time to focus on wearing something that makes YOU feel good. The more confidence you have, the more comfortable you will feel and the more engaged you’ll be! 

Dress ‘age appropriately’

This is not to say that you can’t look youthful or have to dress matronly, but try to pick a sophisticated look that will exude poise and grace. Stray away from showing too much skin or wearing something too tight or short that will look like you are trying too hard. Closet staples like a crisp white shirt never go out of style and you can dress the outfit up or down, depending on the date. Embrace your age and what you have to offer and accentuate your favourite features.

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Complement your outfit with natural hair and makeup

On a first date, it has been shown that less is more. I prefer the natural makeup look because it is really flattering for everyone. This fresh-faced look is not only super easy but is fast to do and you don’t have to be a pro to pull it off; it is all about letting your natural beauty shine and looking effortless. Playing up your features will help you to focus on your date and not give a second thought about your makeup.

A virtual date is still a date

Chatting on the phone or going on a virtual date before you actually meet in person can be a good way to dip your toes in the dating pool or you can use it as a way to decide if you want to go out on an in-person date next. First-date jitters are common and doing a virtual first date might still leave you with butterflies in your stomach. Here are a few tips for you to keep in mind to make a lasting first impression online:

  • Good posture will help you to come across the screen as engaged. Try leaning slightly forward to show you are fully present
  • Sit further back from the camera so your date can see your gestures and so that you aren’t too close to the screen. By showing your nonverbal cues, it will help you to come across as being attentive and can portray warmth and energy that you wouldn’t otherwise be able to if you were too close to the camera
  • Wear what you would wear on an in-person meeting, see above for tips!
  • Don’t forget to add lipstick to help define your smile, since bare lips can get washed out over video
  • Make sure your room is well-lit and that your camera is centred
  • Try to pick a neutral background for your virtual date so that your date isn’t distracted by anything behind you and also to protect your privacy. Make sure nothing too descript is in the camera’s view

Dating Safely

I would be remiss if I didn’t touch on the importance of safety when dating. Here are things to keep in mind and what I have done while navigating the dating world:

  • Mini background checks or Googling your date beforehand. It doesn’t hurt to do some research before you get too invested in someone and can help to determine if someone is worth pursuing or not. Get those deal breakers out of the way early on!
  • Stay alert, limit yourself to one or two drinks and never leave it unattended (the same goes for your food!)
  • Consider a double date and invite a couple you trust. Or try a group date. This can help break the ice and make you feel safer if you are uncomfortable with one-on-one dates.
  • Meet in public at a time when there will be lots of people around.
  • Keep your friends and family in the loop. Let someone know where you are meeting up and what time.
  • Keep your phone charged and near you.
  • Drive yourself so you can leave when you want and protect your privacy until you trust who you are with.

If you find yourself on a bad date after a bad date, don’t give up. Dating can be hard, period. Among the highs and lows, there will probably be rejection from your side and also directed toward you. This is the hard part of dating that you tried to forget the first go around. Try to enjoy the journey with an open heart and mind because you never know when you’ll meet your match!

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About The Author

Kristen Jensen - Lifestyle Specialist

Expert Kristen Jensen

Kristen, the owner of Kristen Jensen Productions LLC., is a lifestyle expert, content creator, author, videographer, photographer and public speaker. As a former international fashion model with Ford Modelsshe made an easy transition to the other side of the lens. Kristen has a wealth of knowledge and experience plus an exceptional eye for those special details that trademark her style bringing an enlightened and gracious touch to advertising magazines, portraits, video and keynote speaking presentations. “I’m in the business of making people feel and look their best, she says about herself. This unique perspective comes as a result of her years in front of the camera.

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