Feeling Confident at Any Age
Let’s face it there are no hard and fast rules when it comes to dating over 50. Simply be yourself, show up wearing something that makes you feel good and confident yet not over think it. Dress in a way that helps you feel attractive yet allows you to relax and have fun not stressing about every detail. These are just a few suggestions to help give you some inspiration.
1. A Well-Fitted Blazer
Blazers are a surefire way to look pulled together and put-together without trying too hard. Make sure yours fits snugly at your shoulders and waist. You want it to look tailored, not rigid. Bonus points if it looks good tossed over jeans or a dress while still feeling comfortable.
2. Dark, Comfortable Jeans
Dark jeans can be your go-to because they work for almost any casual or semi-dressy situation. They’re form-fitting, comfortable, and feel just-usy-like-your-pajamas cozy. You’ll look stylish while still feeling like yourself.
3. A Soft Knit Sweater
As you’ll probably be sitting pretty close or giving those date-night hugs, soft fabric is important. Opt for a lightweight knit in a deep color that feels like a hug and looks chic, not bulky. It also subconsciously tells your date that you value comfort as well as style.
4. A Flattering Wrap Dress
Wrap dresses are a classic for so many reasons. They accentuate your figure while remaining quite forgiving. They’re effortless and something you can dress up or down depending on the plans.
5. Crisp Button-Down Shirt
Button-downs don’t have to scream “corporate America.” Simply leaving the top button undone and slightly rolling up your sleeves can completely change the vibe. It also gives off that “I woke up like this” confidence.
6. Statement Necklace or Bold Jewelry
Speaking of confidence, one bold piece of jewelry can be more powerful than an entire stack of bangles and bracelets. It draws the eye up and will be an instant conversation starter. Trust me, your date doesn’t need to see every sparkle in your jewelry box to be mesmerized.
7. An Easy Midi Skirt
Midi skirts have a way of swishing around as you walk that feels very feminine and effortlessly fancy. Throw on a simple tee and let your skirt do all the talking. Wear this when you’re in the mood to switch up jeans.
8. Leather or Faux Leather Jacket
Leather (or faux leather) jackets are a great way to add some edge and personality to your look. They scream confidence and let your date know you’re down to have some fun. You’ll feel cooler before you even step out the door.
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9. Comfortable Yet Stylish Shoes
While heels are great, your date shouldn’t have to watch you struggle walking in them. Not only will it take away from your confidence, but you’ll probably end up with sore feet halfway through the date. Wear shoes that are cute and comfortable.
10. Tailored Trousers
Trousers are great because like jeans they are form-fitting but can appear more chic. They create nice clean lines for your outfit. It’s a great base to build off of and you can truly wear anything on top.
11. A Dress in a Color You Love
Have you ever worn an outfit that just makes you feel happy? Clothes in colors that you absolutely adore will make you feel that way. They’ll warm up your complexion and bring life to your entire being. Confidence starts with loving what you look at in the mirror.
MariaBeatrice Alonzi on Unsplash
12. A Lightweight Scarf
Scarves are great because they add texture and dimension to your outfit. Not to mention, they’re functional if it gets cold in the restaurant or outside. You can always take it off and hang it around your shoulder. It’s a great accessory that allows your outfit to be flexible.
13. A Classic Watch
Watches are timeless. Wear one and it’ll speak volumes to your date that you love classic style. It’s a subtle way of showing you’re not obsessed with technology and you value quality.
14. A Flowy Blouse
Flowy tops are so comfortable and yet still look so put-together and intentional. They move with your body and won’t cling to any areas you might be self-conscious about. Look for a style with a flattering neckline that you love.
15. Clean, Polished Sneakers
Sneakers can totally work for a date as long as they look clean and aren’t falling apart. They’ll tell your date that you’re effortlessly cool and don’t take yourself too seriously. Another perk is you’ll be prepared if you decide to take a fun stroll after dinner.
16. A Structured Handbag or Tote
Structured bags help tie an outfit together. They give off the illusion that you put more thought into your outfit than just throwing on jeans and a shirt. Not to mention they help you stay organized so you aren’t digging through your bag for your car keys.
17. A Simple Black Dress
A simple black dress is never a bad idea. It can be as simple as that, but make sure the cut or details are modern and something you think you look great in. This is your fail-safe when you want something comfortable with zero thinking required.
18. A Casual Denim Jacket
Denim jackets are the epitome of casual and friendly. They pair amazingly with dresses, skirts, and pants without trying too hard. It’s the perfect solution for looking relaxed but still put together.
19. Thoughtful Grooming and Fit
Please don’t show up to your date with messy hair and crinkled clothes. I can’t stress how important it is to make sure your clothes are not only clean, but also pressed and fit properly. Certain clothes look great off the rack but will look 10x better when tailored to your body.
Katsiaryna Endruszkiewicz on Unsplash
20. Something That Feels Like You
This tip tops them all. Wear something that makes you feel comfortable. If you feel good in your clothes, your date will know. You’re going on a date to get to know each other, not to wear a crazy costume.
