What Senior Men Should Wear On A First Date

Senior Dating

What Senior Men Should Wear on a First Date

April Braswell
April Braswell Posted:
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You put your single self out there, met a sexy senior lady, and asked her out on a first date. Good for you!

But now you’re probably left wondering what you should wear, especially if it’s been a long time since your last first date. Maybe you wore corduroy pants in the ’60s, leisure suits in the ’70s, gold monogram buttons on your blazer in the ’80s, and biker jackets in the ’90s. Well, those fashions won’t really work today.

I’m here to help you make a great first impression and make sure your date can’t take her eyes off you. Read on to discover what senior men should wear on a first date to increase their chances of getting a second date.

Start With a Business Casual Look and Develop It From There

The advice I give to my male senior dating coaching clients is to start with a business casual look and go from there. This is especially helpful if it’s your first date since your divorce or the death of a spouse. You’re being brave enough as it is for getting back into the dating scene, so you shouldn’t have to stress too much about your outfit.

An attractive dress shirt and a blazer can serve as your starting point and be the foundation for your wardrobe. When managing your clothing budget, the blazer is the bigger investment. Splurge a bit on two of those, and then you can buy more budget-friendly dress shirts.

Black and navy are the classic colors for blazers, and they tend to look good on almost everyone. For pants, I recommend khakis. You can dress khakis up if you’re going somewhere kind of fancy, and you can dress them down if you’re going somewhere casual.

Photo of a stylish senior man

If you have a few staple items, you can build a more creative wardrobe with accessories like ties.

It’s good to have one staple outfit, but I also think you should play around with other colors for your other outfits. Be adventurous and bold every now and then.

If you’re feeling sartorial, you can add a pocket square in an accent color. If you’re going for a walk in the park, consider leaving a button or two open at the collar. If you’re going to a restaurant with white table clothes, think about putting on a tie. It’ll take your outfit to the next level, but since you’re not wearing a full suit, you won’t look too overdressed. Get the picture?

The good news is you can find these items at all price points whether you’re at a famous department store, a midlevel department store, or even a consignment shop. Every store regularly offers deals to fit your budget and style, so keep an eye out on their website, on their social media profiles, or in commercials in between your favorite TV shows.

I also recommend getting some professional assistance from the employees at the stores you shop at. You want to have someone else’s opinion to confirm that the colors you chose are flattering to you and that the attire is well-constructed. These employees can also make sure you’re getting the right size. So many men I know are wearing clothes that don’t properly fit them. They’re either too small or too big. It’s amazing what wearing the right size will do for your appearance.

Be Consistent with the Man You Are — Just the Dapper Version

If you’re not preppie, you don’t have to suddenly don the latest line from Brooks Brothers. If you’re not country or Western, you don’t have to buy the coolest new cowboy boots.

Your senior lady wants to see the man you presented yourself to be when you two first met. She’s interested in you. You don’t have to dress to be an entirely different man. You just need to spiff up and be the dapper version of that same man.

Know the Style for Your Geographic Region

Don’t worry. I’m not suggesting that you have to have every style tip from GQ magazine memorized. However, you should know what’s in style in your region and what’s not.

For example, if you’re in a tropical location, it doesn’t make sense to wear a suit for a first date. An open-collar dress shirt will do. You don’t even need a tie or blazer. If you live in the Northwest, and it’s fall or winter, it probably doesn’t make sense to wear shorts or flip flops on a first date.

Next time you run errands around town, take notice of what other men are wearing, especially younger men as they’re more likely to know what’s in and what’s out. That’ll give you a few ideas for what you should look like.

Dressing Up Should Be Fun, and It’ll Show Your Date That You Care

I’ve had many single midlife men — whether it’s a friend, a family member, or a coaching client — complain to me, “Why do I have to dress up for a first date? Doesn’t she want to see the man I am every day?” And, I hate to say it, but more often than not, that comment comes from a single-never-married man and/or a man who hasn’t learned that women are visual creatures, too.

Photo of man looking in mirror

This isn’t just about looking good. It’s about feeling good. When you feel good, you’re more likely to be yourself on a date.

There are senior women who literally will never consider a man as a serious romantic contender if he doesn’t know how to dress properly for a date, whether it’s the first or 10th date. It’s a sign of respect to your date if you invest some time in your appearance.

Making an effort can also be fun. You aren’t just doing this for her. You’re doing this for yourself. You get to express yourself through your outfits. Not to mention when you look good, you feel good. Nothing is more attractive than a confident man. Make sure you feel like your authentic best self.

Once you’re looking your best, you’re truly ready to impress your date on that first romantic outing. Happy dressing, and happy dating!