As men over 50 age, their wardrobes undergo a subtle yet significant transformation. Gone are the trendy and fleeting fashion statements, replaced by timeless and sophisticated styles that exude confidence and comfort. A man’s casual wear is a reflection of his personality, attitude, and place in life – it’s a means of expressing himself authentically. Three key considerations for older men when selecting their everyday attire are fit, comfort, and luxury.
The result is a wardrobe that mirrors the refined gentleman he has become.
How To Dress In Fifties For Guys
When it comes to dressing casually as a mature man, there are certain guidelines to follow. Firstly, avoid the temptation to dress younger than your age – this can come across as insincere and may not accurately reflect your personality. Instead, focus on creating a cohesive look by sticking to a color-blocked wardrobe. Avoid bold or bright colors that may draw attention away from your overall style.
On the other hand, opt for smart, casual shoes that complement your outfit without overwhelming it. Additionally, refrain from wearing sneakers or brightly colored shoes, as these can give off a more casual and unrefined impression. By following these simple tips, you’ll be well on your way to developing a stylish and confident everyday look.
↓ 30 – Summer Dress Shirts
While many men over 50 prioritize comfort and decency in their attire, casual dress shirts often prove to be the perfect blend of both qualities. Not only do they provide a sense of relaxation, but they also exude a level of sophistication, making them an ideal choice for formal occasions. For individuals seeking stylish yet comfortable clothing, popular brands such as Banana Republic, Uniqlo, Bonobos, Everlane, and J.Crew are excellent options to consider.
↓ 29 – Dark Colored T-shirts
For men over 50, a stylish wardrobe staple is the humble T-shirt – specifically, dark ones. While any color will do, there’s something undeniably sleek about a well-chosen dark T-shirt that adds to their timeless appeal. Not only are these shirts comfortable and effortlessly casual, but they also exude a certain air of sophistication, courtesy of high-end brands like Gucci, Versace, Lacoste, Ralph Lauren, Puma, Abercrombie and Fitch, and River Island.
Whether you prefer to shop in-store or online, there’s no shortage of options to suit your taste.
↓ 28 – Sneakers & Tee For Casual Look
When it comes to creating a casual yet stylish outfit, simplicity is often the key. A plain or colored shirt paired with comfortable trousers or pajama pants can make for a great combination that exudes a sense of relaxed sophistication. To take the look to the next level, add a hat and a pair of quality sneakers. This ensemble is versatile enough to be worn on everyday casual occasions, as well as more adventurous activities like boating trips.
Feel free to swap out the sneakers for boat shoes if you want to dress up the outfit for a water-based excursion.
↓ 27 – Easy Going Jeans
Regardless of age, jeans remain a timeless fashion staple that can elevate any outfit. Whether you’re 20 or 50, jeans offer a versatile and stylish look that’s suitable for any occasion. They pair well with a wide range of shirts, from casual to dressy, making them an excellent choice for everyday wear.
While there are many great brands out there, such as River Island, Levi’s, and Calvin Klein, I believe it’s best to steer clear of ripped jeans and instead opt for high-quality denim that exudes sophistication.
↓ 26 – Simple Shorts
When it comes to summer fashion, shorts often take center stage as a staple in many men’s wardrobes. Not only do they provide relief from the warmth, but they also exude a sense of effortless cool and sophistication. For mature gentlemen, finding a pair that strikes the right balance between comfort and style can be a challenge. However, some exceptional brands have risen to meet this demand, offering high-quality shorts that are perfect for hot summer days.
Polo Ralph Lauren, Everlane, The Upside, and J. Crew are just a few notable examples, each bringing their unique touch to the classic short design.
↓ 25 – Button Down White Dress Shirt
Men over 50 can exude confidence and professionalism with formal dress shirts as their go-to attire. This timeless style is perfect for work, interviews, business meetings, or any other formal occasion. For a sleek and affluent look, opt for high-quality formal dress shirts that make you feel like a million bucks. Brands like Brooks Brothers, Joseph A.
Bank, and Ralph Lauren are iconic players in the men’s fashion industry, offering classic designs and exceptional quality that caters to baby boomers and beyond.
↓ 24 – Casual Printed Shirts
For individuals who crave excitement and flair in their wardrobe, printed dress shirts offer an unparalleled level of versatility and style. These shirts, with their vibrant colors and engaging patterns, provide a relaxed yet put-together look that can be effortlessly paired with jeans or trousers to create a cohesive and stylish ensemble.
Brands like Stacy Adams, Boss Hugo, and JCPenny are renowned for crafting high-quality, fashion-forward printed dress shirts that cater to this unique sensibility.
↓ 23 – Solid Colored T-shirt
T-shirts have long been a timeless fashion staple that transcends age boundaries. While often associated with younger men, they can be just as stylish and appropriate for individuals over 50. A plain T-shirt is an excellent choice for a summer outfit in this age group, offering a perfect blend of casualness and sophistication. Top brands that excel in creating high-quality T-shirts include Express Inc, Kenneth Cole, Jack Wills, Dolce & Gabbana, and Iwin Clothing, among others.
↓ 22 – Tank Tops
For a man looking to make a stylish statement, a sleeveless tank top is an excellent choice. Not only is it incredibly comfortable to wear during the summer months, but it also provides a sleek and sophisticated aesthetic that’s sure to turn heads.
↓ 21 – T-shirt With Jeans
For a polished appearance, pairing a T-shirt with jeans is always a winning combination. This laid-back yet stylish look is perfect for older gentlemen on a daily basis, making it an excellent choice for casual summer outfits. When it comes to selecting the right jeans, consider reputable brands like Levi’s and River Island, or opt for high-end labels such as Dolce & Gabbana.
Meanwhile, T-shirt enthusiasts can explore reliable options from H&M and Iwin Clothing, or splurge on luxury brands like TXC Brand and Burberry.
↓ 20 – Dress Shirt With Jeans
For a more polished appearance, pairing jeans with dress shirts is a great option. You can either tuck the shirt in or leave it untucked, depending on your personal style and the occasion. This combination works well for formal events and can be dressed up or down. Consider pairing your jeans with high-quality dress shirts from brands like River Island, Banana Republic, J. Crew, or Topman. To complete the outfit, add a tie from The Tie Bar or a similar brand.
For the perfect jeans to wear with your new look, consider styles from Gucci, Guess, Levi’s, or Escada.
↓ 19 – Leather Belt
When it comes to elevating a man’s style, combining a T-shirt with jeans and a high-quality leather belt can make all the difference. These accessories not only add a touch of sophistication but also exude luxury and refinement. To achieve this look, men can opt for stylish leather belts from renowned brands like Ralph Lauren, Stussy, Anderson’s, and Fjallraven, which are available on their online stores.
↓ 18 – Muscle Fit Style T-shirt
Maintaining a healthy physical appearance is crucial for overall well-being. Regular exercise helps to achieve this goal, and as a result, it’s always beneficial to opt for clothing that accentuates your physique. Slim-fit or tailored shirts are excellent choices when you’ve put in the effort to tone your muscles. These styles of shirts not only provide a flattering fit but also create a sense of confidence and self-assurance.
Brands like GAP, Giordano, and The Texture offer high-quality options for those who value their physical appearance and seek to showcase their hard-earned results.
↓ 17 – Pocket Style Casual Shirt
For a relaxed yet stylish appearance, consider opting for a pocket-styled shirt. This versatile look is perfect for everyday casual wear and can be easily dressed up or down to suit various informal events. Brands like Burberry, Prada, Hartford, and Ralph Lauren are renowned for their high-quality pocket-styled shirts that exude effortless charm.
↓ 16 – Khaki Pants
Pairing casual shirts with khaki pants is a timeless combination that exudes elegance and sophistication. The slim-fit linen shirt in particular, when worn with khaki pants, creates a stylish ensemble that’s perfect for everyday wear. This classic combination works beautifully with a range of tops, including white, navy, and pastel-colored t-shirts or polo shirts from renowned brands such as Nordstrom, Topman, and Zappos.
↓ 15 – Relaxed Pants
When it comes to dressing down, casual pants can be a great option. Pairing them with a T-shirt creates a decent and slightly formal look that exudes maturity. This style is particularly well-suited for men over 50, as the relaxed fit of the pants adds a touch of sophistication to their overall appearance. Brands like John Players, Raymond, Van Heusen, Peter England, Blackberry’s, Park Avenue, Louis Philippe, and Invictus offer high-quality casual pants that are perfect for this look.
↓ 14 – Pocket Style Dress Shirt
A pocketed dress shirt is a stylish and sophisticated choice for formal occasions. Whether you’re heading to a job interview, a networking event, or a black-tie affair, this classic design exudes professionalism and elegance. The subtle addition of a pocket adds a touch of refinement, making it an excellent option for those seeking to make a lasting impression. Top brands like Thomas Pink, T. M Lewin, Charles Tyrwhitt, J.
Crew, Club Monaco, and Brooks Brothers offer high-quality examples of this timeless design, perfect for dressing up or keeping in your wardrobe’s arsenal.
↓ 13 – Short Sleeved Suit
For men over 50, a sleeved suit – also known as a safari suit – is a staple of formal wear that can be dressed up or down to suit various occasions. Whether attending a business meeting, job interview, or simply enjoying a leisurely stroll in the park, these suits exude an air of sophistication and elegance. Made from a range of fabrics including linen, wool, and nylon, the choice of material often depends on the season or weather.
Well-known brands like Raymond, Vimal, and Mayur Suitings offer high-quality sleeved suits that cater to diverse tastes and preferences.
↓ 12 – Formal Pants With Suspenders
Men over 50 can exude a sense of sophistication and professionalism by incorporating formal pants with suspenders into their wardrobe. This classic combination is perfect for formal occasions such as office settings, meetings, interviews, and events. The addition of suspenders adds a touch of elegance, making it an excellent choice for those looking to project a confident and put-together image.
With various types of suspenders available, including clip-on, button-on, and work suspenders, individuals can easily find a style that suits their personal aesthetic.
↓ 11 – Check Shirts
Printed dress shirts offer a unique and stylish approach to dressing. The vibrant prints and patterns can be paired with both jeans and trousers, making them suitable for both casual and formal occasions. Brands like J.Crew, T.M. Lewin, Club Monaco, Brooks Brothers, and Thomas Pink are known for their high-quality printed shirts that exude sophistication and elegance.
↓ 10 – Funky Shirt With Hats
When looking to add a touch of whimsy and casual flair to your outfit, pairing funky shirts with hats can be a winning combination. The resulting look embodies a vibrant and carefree personality, exuding a sense of fun and playfulness. When it comes to selecting the perfect hat to pair with your statement shirt, consider iconic brands like Brixton, J. Barbour and sons, Borsalino, Lock and Co.
Hatters, or New Era Cap Company – Christy’s are also great options, offering a range of stylish designs that can elevate your entire look.
↓ 9 – Collared T-shirt Styled
When it comes to dressing up for formal events or office attire, collared T-shirts are a popular choice. They exude a sense of professionalism and modesty, making them an excellent option for both men and women. To complete the look, pair your collared tee with trousers or a skirt for a put-together appearance that’s perfect for formal gatherings.
Some well-known brands that offer high-quality collared T-shirts include Tommy Hilfiger, Burberry, Brooks Brothers, Hugo Boss, Fred Perry, Ralph Lauren, and Lacoste.
↓ 8 – V-neck T-shirt
V-neck T-shirts are a staple for casual outfits, often paired with jeans or shorts for everyday wear. Top brands like Calvin Klien, Adidas, Hollister, and Tommy Hilfiger offer high-quality options in this style. With their versatility and timeless appeal, V-neck T-shirts are a must-have addition to any wardrobe.
↓ 7 – Plain T-shirt With Shorts
When it comes to creating a carefree and relaxed summer outfit, shorts are an excellent choice. Not only do they offer a stylish addition to your wardrobe, but they also provide comfort during the warmer months. As informal wear, shorts can be worn in various settings, making them a versatile staple for any summer look. If you’re looking to upgrade your shorts game, consider checking out top brands like Tommy Jeans, Everlane, Ralph Lauren, The Upside, and P.
E Nation, which offer an array of stylish and comfortable options.
↓ 6 – Casual Dress Shirt With Trousers
When it comes to summer formal wear, casual dress shirts paired with trousers are a timeless and versatile choice. The combination can be elevated to a more classic and professional look by adding a tie. This stylish ensemble is perfect for office settings, formal meetings and gatherings, as well as special events.
For those seeking high-quality options, brands like Anna Matuozzo, Battistoni, Ralph Lauren, Barba Napoli, Brioni, Charles Tyrwhitt, Hilditch And Key, Brooks Brothers, Gitman, Lorenzini, Charvet, Emanuele Maffeis offer exceptional casual dress shirts. For trousers, reliable choices include Uniqlo, Beams, J. Crew, Cos, Incotex, Acne, Wooyoungmi, and Theory.
↓ 5 – High-waist Trousers
Pairing high-waisted trousers with crisp dress shirts creates a sharp, stylish look. When combined with a quality belt, this ensemble is perfect for formal events. The versatility of these trousers makes them suitable for nearly any occasion that requires a touch of sophistication, from business meetings to black-tie gatherings.
↓ 4 – High Waist Trousers With Suspenders
When it comes to styling high waist trousers, another great option is to pair them with suspenders. Not only do they make for a sharp and stylish outfit, but they’re also an excellent choice for formal occasions. And when it comes to finding the perfect suspenders, there are many great brands to choose from, including John Deere, Trafalgar, Carhartt, and Harley Davidson – all of which offer high-quality options that will complement your trousers perfectly.
↓ 3 – Single Collar Polo Shirt
The single collar polo shirt embodies a relaxed summer vibe, making it an excellent choice for everyday wear. Its versatility allows it to be paired with both trousers and jeans, perfect for casual outings or simple daily activities. When it comes to quality brands offering this style, Lacoste, Ralph Lauren, Burberry, and Tommy Hilfiger are notable mentions.
↓ 2 – All Jeans Attire
Pairing a denim shirt with jeans pants creates a effortlessly chic and casual outfit that’s perfect for everyday wear. This stylish combination looks great on men and is suitable for any occasion that calls for relaxed yet put-together attire. Brands like Van Heusen, Roadster, Blackberry’s, and Here&now offer high-quality denim shirts that are sure to elevate your wardrobe.
↓ 1 – Dress Shirt with Shorts
When it comes to creating a relaxed yet stylish outfit, pairing dress shirts with shorts is an excellent option. This combination offers a perfect blend of comfort and versatility, making it ideal for casual summer gatherings or everyday wear. The result is a look that exudes effortless cool, allowing you to transition seamlessly from a day out with friends to a night out on the town.
Frequently Asked Questions
Q. What Not To Wear In Your 50s?
When dressing down, it’s often best to keep things straightforward and unassuming. Opt for trousers in solid colors or subtle patterns, and steer clear of bold designs or ripped jeans. Similarly, when it comes to footwear, eschew high-top sneakers and instead choose shoes that exude a sense of maturity and sophistication.
Q. Where To Shop From?
In our previous discussions, we’ve explored the top brands for various clothing items. When it comes to men’s fashion beyond their 50s, a select few stand out from the rest. Our top three recommendations are Marks&Spencer, Oliver Spencer, Mr. Porter, John Smedley, and Lacoste – each offering something unique that resonates with this demographic.
Q. Can I Wear Skinny Jeans in 50s?
For those who exude confidence when wearing skinny jeans, there’s no logical justification for abandoning this wardrobe staple. Its comfort factor is undeniable, making it a great choice for everyday wear.
