FASHION & BEAUTY Just for Men  >  Menswear 101: Four Tips for Men over 50 Who Want to Look Their Best

Menswear 101: Four Tips for Men over 50 Who Want to Look Their Best

Menswear 101: Four Tips for Men over 50 Who Want to Look Their Best
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By Naakai Addy

Men’s fashion has enjoyed cyclical changes in almost every culture for centuries. The styles in vogue have matched the social attitudes and political climate in each time period, so it’s no surprise that a more open-minded America has adopted playful attitudes towards menswear for men over fifty. Even if you played it safe back in the day, don’t be afraid to breathe new life into your sense of style. From finding the right tailor to getting bold with color choices, here are four tips on how men over 50 can look their most handsome.

  1. Make the trends work for you

Events like Men’s Fashion Week have brought the creativity and exquisite tailoring inherent in today’s menswear to the forefront. Trends like skinny jeans and sheer shirts make seem too extreme to even be worth your notice, but a loose interpretation of these trends can be liberating.

Seventies’ style has made a major comeback, but rather than going for full-on bellbottoms, keep it classy with a subtle homage to the era. A light jacket with a wide, seventies-style collar in a modern fabric is just one way to stay on trend without looking like you’ve forgotten which century it is.

This season is also the perfect time to play around with patterns. Start small if you’ve never gone beyond pinstripes. Subtle florals and abstract prints add appropriate flare to a classic pair of trousers or jeans and a solid jacket.

  1. Find a trustworthy tailor

Getting older inevitably brings physical changes, but your wardrobe doesn’t have to suffer as a result. Have suits or separates that you’re determined to keep? Finding a great tailor can be the key to updating or rejuvenating an existing wardrobe. Minor alterations such as removing shoulder pads and altering waistlines are fairly cheap, and they give you the opportunity to test out the tailor and see how they handle your garments. Start with pieces in your wardrobe that are less expensive, and work up to the major ones once you trust the tailor.

If you don’t have a trusted tailor yet, read Yelp reviews about your local alteration shops. A good tailor can tell you upfront how much the alteration will cost, how long it will take, and will spend time getting an accurate sense of how you want the finished product to look. Services like Indochino ( take your measurements and send you clothes tailored specifically for you.

  1. Let someone else build your wardrobe

Investing in quality is especially essential as you get older, so now is not the time to drop the bar on durable fabrics and flattering cuts. Fortunately, there are several services out there that do all of the shopping for you; all you have to do is tell them a little bit about your size and sense of style. The marketing for many of these services targets men in their mid-late 20’s, but the personal stylists who work there understand how to make an older gentleman look confident in his own skin.

The top menswear services include ThreadTread (, Trunk Club (, and The Mr. Collection (, where you pay a monthly fee to be shipped high-quality suits, shirts and casual wear worthy of James Bond. In most of these services, you can select the amount of garments you’d like at a time, as well as the level of formality you need to supplement your existing wardrobe.

  1. Groom like a gentleman

The most important finishing touch to any debonair ensemble is a fresh haircut and facial hair that looks deliberate. Whether your signature style includes a shaped beard or a clean-shaven visage, grooming can be an almost therapeutic ritual and is an essential component to gentlemanly style.

Fortunately for men, greying hair can be the badge of a silver fox. The trick? Keeping those greys healthy, moisturized, and as full as they can be. Top brands like American Crew ( offer salon-quality haircare for men; these products are designed to make your hair the best it can be. If you’re going to dye your hair, work with a hairstylist to find a shade that matches your skin tone and doesn’t look unnatural or overprocessed. Any bald spots are best embraced, as covering them up rarely looks authentic or confident.

For decades, men’s shaving products seemed to be getting increasingly more disposable, but classic shaving kits are finally making a comeback. The benefit of a high-quality razor and natural shaving creams is less razor-burn, smoother skin, better precision and longer-lasting results. Find updated takes on vintage shaving products at modern-day grooming havens like The Art of Shaving ( and Dr. Sofkins (

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