Confidence Dressing: What To Wear On A First Date When Over 50

Are you over 50 and getting back into the dating scene? It’s never too late to find love, but if we really never get a second chance to make a first impression, then when it comes to first dates it’s better to get it right.

Having been out of the game for a while can make women over 50 feel a bit rusty but that doesn’t mean they should neglect their look, especially if they hope to score a second date.

Remember, the key to confidence dressing is to be true to yourself and to showcase your unique style. Let CrunchyTales help you out with some tips.

First date outfits: dos and don’ts

As a rule of thumb, though the best outfit for a first date depends largely on where you’re going and what you’ll be doing, it’s best to stick to simple outfits using classic styles that make you feel confident. 

The goal is for your first date outfits to seem effortless and while you don’t want to look overdressed, you don’t want to look sloppy either or someone who is trying too hard.

• Avoid anything too-fitting (from super tight tops to shoes that rub), as you might spend the whole evening fiddling with your outfit, which is never a good look.
• Do show off your best part, focusing on revealing your long elegant neck, your shoulders or toned arms but without revealing too much (showing a bit of cleavage on a first date may help catch your partner’s attention, but showing too much may actually hurt your chances of finding love).
• Just remember the golden style rule; if you’re showing off your legs, keep your chest covered with a high neck design or vice-versa.

But don’t worry, chances are you have a capsule wardrobe full of items that can easily be styled for a first date. From your best jeans to the best dresses, whatever you decide to wear, there’s one key thing to remember, be comfortable. According to Rachel Sommer, PhD, a clinical sexologist and relationship expert, “being comfortable breeds confidence, ultimately translating to more smiles and genuinely engaging with your date.” 

The best first date outfits for confidence dressing 

Ultimately, what we wear has cognitive, social and emotional consequences. They not only affect other people’s opinions of us but can also alter our moods.

Professor Karen Pine, a renowned psychologist from the University of Hertfordshire and the author of the book “Mind What You Wear”, has explained that clothes have mind-altering properties. 

“I believe we can feel happier and more confident in the right clothes. And now science confirms that not only are we what we wear, but we can also actually become what we wear“, she says.

Amongst the items likely to induce a more positive mood and confidence in the wearer she includes:

• a well-cut dress in a beautiful fabric (a flared peplum shape, for example)
• flowered prints, lacy tops and floaty fabrics (which are associated with spring, making us feel ultra-feminine and glowing with health)
• mismatched pieces (e.g. a leather jacket over a floaty dress, formal with informal, vintage with new, give us a buzz because the brain enjoys novelty and surprise).

When it comes to accessories, Professor Pine encourages you to be a bit more daring. They are a good way of injecting some personality into your look without going overboard, so opt for a bold piece that can provide your date with a snapshot of your personality.

However, there is a special accessory she always recommends: your smile: “If you smile whenever you wear an item of clothing, you’ve probably found the right piece for you“, she concludes.

In the end, your outfit should reflect your personal style. Wearing clothes that are comfortable and practical allows you to stay fully engaged in the conversation.

Try different outfit combinations 

When it comes to choosing your outfit for your first rendez-vous, you have also to consider whether it’s a daytime or evening date. 

• Daytime

The first one tends to be more casual than the latter, so a stylish top to wear with jeans is a fail-safe option and when paired with a colourful or printed blazer, strikes the perfect smart-casual balance. Add a pair of ballet pumps and a structured bag and voilà you’ll have a pulled-together look. If you need an extra layer, your best trench coat will keep you warm and smarten up the look in case it runs into the evening, which is definitely a good sign.

• Evening

On the other end, a dinner date invitation requires a little more effort. As a general rule, a simple fitted knee-length dress is a foolproof option. Opt for a slim fit (not super-tight) style with a ruched middle that will help minimize your waist and create a smooth silhouette, then ring changes with a statement necklace or drop earrings and add classic mid heels as an elegant way to finish off your look.

Having said that, there’s rarely a need to do an entire closet overhaul when prepping for a first date. On the contrary, getting ready for a first date is about nailing down your personalized formula, rinse and repeat. Good luck.

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