5 Date Night Outfits For Men Over 50 (2024)

Whether you’re happily married and want to remind your other half that you’ve still got it, or you’re single and ready to mingle, these date night outfits for men over 50 are destined to get pulses racing.

Following on from our guide on how to dress sharp, we thought it was important to show you some prime examples of what men over 50 should wear on all-important date night.

At the end of the day, older men should be able to dress stylishly and stay in fashion.

The key to getting this right is remembering that less is more. Keeping your outfit simple and smart will tell your love interest that you aren’t desperately trying to stay “down with the kids” and haven’t yet conformed to old man, loose-fitting sweaters and bootleg jeans.

Dress appropriately on a date night and it’ll reignite some of that honeymoon magic back in the day – ooh la la! With this in mind, here are some examples to inspire your selection.

Men's date night outfits for over 50s

Tweed grey

5 Date Night Outfits For Men Over 50 (1)

If you have grey hair, then wearing an all-grey outfit for date night oozes sex appeal. Complement a stylish three-button grey tweed blazer with a lighter or darker great sweatshirt (if cold) and a crisp white shirt.

Finish the look off with a rich blue pocket square, patterned pair of grey trousers and a pair of smart Derby or Oxford shoes.

Waistcoat wonders

The next date night outfit for men over 50 involves a waistcoat. You only have to cast your mind back to the 2018 FIFA World Cup to remember the power of Gareth Southgate’s waistcoat attire.

The problem with a statement coat alone is that you’ll have to take it off as soon as you arrive. But with a waistcoat, you can maintain your smart appearance as you sit and enjoy the company of your other half.

Ideally, pair a muted-coloured waistcoat with a brighter/softer blue shirt – like the examples provided.

The statement

5 Date Night Outfits For Men Over 50 (2)

As we mentioned in our previous fashion over 50 article, investing in a statement piece of clothing such as a coat or scarf can elevate any outfit.

For example, adding a smart trench coat, pea coat or overcoat to a pair of dark blue jeans, white shirt and black or brown pair of Oxfords will ensure you make a perfect first impression on your date. For extra brownie points, include a statement scarf which matches with the coat – just like Mr Bond.

Summer vibes

5 Date Night Outfits For Men Over 50 (3)

When the sun is shining, you’re going to need a date outfit that doesn’t make you feel the heat. Channel beautiful Italia and long exotic sandy beaches with a white shirt (rolled-up sleeves), khaki chinos/trousers, a light brown belt and matching loafers.

Full marks if you have a stunning brown-strapped watch.

Turtleneck triumph

5 Date Night Outfits For Men Over 50 (4)

Turtlenecks are a prime example of how younger trends can work in men’s fashion over 50 too. Buy yourself a smart brown one and wear it with a brown tweed blazer/beige/khaki chino combination.

Or if it’s a more casual date, wear a white turtleneck with dark blue or black jeans and a pair of Oxfords or chukka boots.

Pay close attention to the shoes

You can spend all the money in the world on a date night outfit, but if you opt for an old tired pair of shoes, you’re going to undo all of your hard work. In fact, an article in Cosmopolitan revealed that women can tell what kind of partner you’ll be by simply looking at your footwear choice!

Picking a smart pair of Oxford shoes from our collection will tell your date that you’re a smart person and that you take care of your appearance. It also indicates that you’re taking your date seriously, as you’re clearly making an effort.

Simply start with a pair of Percy Strides and the rest of your date night outfit will fall into place.

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5 Date Night Outfits For Men Over 50 (2024)

FAQs

What should a 50 year old man wear on a date? ›

For example, adding a smart trench coat, pea coat or overcoat to a pair of dark blue jeans, white shirt and black or brown pair of Oxfords will ensure you make a perfect first impression on your date. For extra brownie points, include a statement scarf which matches with the coat – just like Mr Bond.

What style should a 50 year old man wear? ›

If you're not sure what to buy, go for a trim, two-button jacket with wider lapels and well-tailored, flat-fronted trousers. Give your ties a bit of a refresh, and if you're feeling adventurous, replace those old, tired dress shirts with a cool rollneck jumper.

What do men over 50 look for in a relationship? ›

Older Men Want Women To Be Themselves.

In a similar way that they want to be accepted as who they are, men also expect women to be themselves. They appreciate the spirit of compromise, but they want a partner who shows their true character.

How should a 60 year old man dress casually? ›

Here are a few examples of chic and casual outfits that are suitable for men in their 60s:
  1. Dark, well-cut jeans with a nice T-shirt under a cardigan.
  2. Tailored chinos with an untucked button-up.
  3. Dress pants with a nice polo shirt and fitted blazer.
Mar 24, 2022

How do I impress a 50 year old man? ›

Many old guys will be turned off if you are just looking for someone to take care of you. In other words, have a steady job and a well-established house or apartment. If an older guy is looking at you, those qualities will show him your mature enough to date him. Keep your cool.

What to wear on a night out in your 50s? ›

Wear with a white t-shirt, blazer and heels for a laid-back evening look or with a relaxed blouse and sandals in the summertime. Wide leg jeans are the current favourite style but go for a style that you feel flatters your height and body shape to keep them in your wardrobe rotation after the trends have passed.

How to look trendy at 50? ›

Our top 5 style tips for what to wear at 50
  1. Embrace color. While you can never go wrong with a dependable neutral color, bright and bold hues add excitement to your closet. ...
  2. Invest in luxe knits. ...
  3. Play up your waistline. ...
  4. Find your perfect fit. ...
  5. Chic loafers. ...
  6. A smart blazer.
Feb 15, 2024

What type of jeans should a 50 year old man wear? ›

Straight Leg Fit

Nothing can beat the timeless style of classic straight-leg jeans. This cut of jeans is well tailored to the body of older men and is well suited to their styles.

What not to wear if you are a man over 50 casual? ›

8 Mistakes Older Men Make Trying to Look Young
  • Wearing Athletic Clothing Outside the Gym.
  • Wearing Sneakers Incorrectly.
  • Wearing Baseball Caps as a Casual Accessory.
  • Wearing Tight, Trendy Clothing.
  • Wearing Unflattering Jeans.
  • Dressing like a College Boy.
  • Wearing Excessive Colors and Patterns.
Mar 20, 2024

What are the red flags for dating at 50? ›

By being aware of these eight red flags – rushed intimacy, lack of communication, inconsistent behavior, financial red flags, isolation from loved ones, avoidance of commitment, unresolved baggage, and trusting your instincts – you can enhance your chances of finding a fulfilling and lasting relationship.

How to flirt with a man in his 50s? ›

Flirting: 9 Basic Guidelines for the Mature Single
  1. Direct looks and genuine smiles. Your face is what they see. ...
  2. Subtlety. Ladies, men admire an understated approach, and men, women do too. ...
  3. Sincerity. Everyone likes a compliment—as long as it's genuine. ...
  4. Body Language. ...
  5. Touch. ...
  6. Conversation. ...
  7. Humor. ...
  8. Attention.

How to tell if an older man is attracted to you? ›

1 He opens up to you. 2 He shows genuine interest in your life. 3 He makes an effort to spend time with you. 4 He tries to help you out, however he can.

What should a 60 year old man wear on a date? ›

So, opt for a straight-cut but nothing overly baggy. They'll tell you this already, but you should look for blazers and not suit jackets, as these will be far too formal. Find one with decent shoulder pads so you look broader and stand straighter, and wear it with some smart jeans or chinos.

How should a 52 year old man dress? ›

How A Man Should Dress In His 40s and 50s
  1. Avoid Big Logos. As your age increases, the amount of visible branding on your clothing should do the opposite. ...
  2. Approach Sportswear With Caution. ...
  3. Keep It Classic. ...
  4. Keep Colours Muted. ...
  5. Focus On Fit.

What pants should a 60 year old man wear? ›

Slim Jeans for Older Men – And the Younger Ones, Too

As you get older, skinny jeans are a style you've likely aged out of. That doesn't mean you should be avoiding all slim styles, though. Some of the best jeans for older men are slim-leg pairs that are comfortable, age-appropriate, and stylish.

What do guys want girls to wear on a date? ›

For women, go with a little black dress or a casual blouse and jeans finished with feminine accessories and a natural makeup look. Stick to solid colors or small-scale prints and avoid anything with loud patterns and obnoxious colors that may distract your date.

How do I meet a good man over 50? ›

We'll also give you some tips on how to make the most of these opportunities!
  1. Local Bars. Local bars can be great places to meet men over 50. ...
  2. The Gym. The gym is a great place to meet men over 50 for many reasons. ...
  3. Sporting Events. ...
  4. Social Clubs. ...
  5. Church Groups. ...
  6. Book clubs. ...
  7. Online Forums. ...
  8. Volunteering Organizations.
Jul 11, 2022

What age range should a 50 year old man date? ›

The “creepiness rule” states that the youngest you should date is “half your age plus seven.” The less commonly used corollary is that the oldest you should date is “subtract seven from your age and double it.” According to this rule, society should accept a 50 year old man dating a 32 year old woman.

What to expect on a first date over 50? ›

Starting your first date in your 50s can be a fun and exciting experience. With the right mindset and preparation, you can make your date a success. Remember to choose a comfortable location, dress appropriately, be open-minded, listen actively, avoid talking about past relationships, stay positive, and be yourself.

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