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The Essential Guide to Style in Your 40’s

The Essential Guide to Style in Your 40's

An essential guide to style

A man’s style evolves over the years, reflecting his age, status and the multiple roles he plays at a given time of his life. Your style can be influenced by your job, relationship status, family and more, projecting your identity to others and the way you view yourself.

By the time your reach your 40’s, you should have the experience, knowledge and self-awareness of how to look like a man of great style. It’s this time in life when most men establish a confidence in their identity and apply that to what they wear, knowing what works and what reflects the image they want to project.

In fact, the 40’s may be your most stylish decade for a number of reasons. First, you are still young enough that your body can be fit and trim, allowing you to wear clothes that fit complimentary and are made by the world’s best designers.

Secondly, you’ve pretty much moved past “fashion” and trends and are focused more on style – and there is a difference. It’s not often that later in life, a man will see a photo of himself and be embarrassed by what he was wearing in his 40’s.

Also, a man in his 40’s can still dress in clothes that can be considered a younger man’s item without looking out of place. We’re not saying you should be shopping at an American Eagle store, but the 40’s allow you to dabble in the younger man’s style and of that of a more distinguished gentleman.

Finally, in your 40’s, many men have the means to purchase those quality items they may not have purchased in their younger days. The 40’s is when you really begin to invest in yourself and what you wear.

As your style evolution evolves with age, it can be confusing as to what works and what is appropriate. The following is an essential guide to style for men providing tips and ideas to allow you to keep turning heads and feeling good well into your 40’s.


Fit first

This is important no matter what your age or style, but it’s particularly important as you find yourself in your 40’s. It’s at this time, you lose more control over the shape of your body. Even if you are somewhat active and eat well, things start to change. So you want to make sure that your clothes fit properly to best compliment your body type, no matter what it is.

It’s probably in your 40’s that you can donate your ‘skinny’ fitted clothing, including jeans, tight sweaters, etc. We believe in dressing what makes you feel good, but skinny fitted clothing isn’t somewhat age appropriate in this decade.

perfect fit clothing for men
Proper fit should be your priority


Any essential guide to style – no matter the decade – is fit over colour and nuances of style. In fact, if you haven’t already, your 40’s is the ideal time to dive into the world of custom or bespoke suiting.

Whether it’s a suit, pants, shirt or even coat, if it doesn’t fit right, move on to something else.


It’s time for the essentials

Obviously your style is driven by your personality, the various roles you play in life and what makes you feel good. For the majority of men in their 40’s, they may be moving into management positions or roles of authority. Many are husbands, fathers, Little League coaches and other distinctive titles.

It’s at this time to start to dress to fit these roles, so it’s a good idea to ensure you have what we would call wardrobe essentials, because they never really go out of style. Some may consider this moving to a more conservative or traditional style, but there’s a reason they are called essentials. Because they are timeless and they look great.


wardrobe essentials


For this essential guide to style for the 40-something man, we’ve provided a link to our overview of some of our 15 recommended essentials that never go out of style, with more recommendations later in the article.


Time to lay off the street/sportswear

In the last 10 years or so, there’s been a massive growth in popularity in street or sportswear in a young man’s everyday wardrobe. If you’re a reader of GQ magazine, at least the American publication, you would see that this style makes up the majority of their features now. And it looks great on the athletes and young actors they profile in the magazine, but there’s a reason why you won’t see the same style applied to men in their late 30’s, 40’s and beyond.

athleisure wear
Avoid the athleisure wear in your 40’s

Partly due to the importance of fit listed above, but mainly due to the fact that athleisure wear outside of the house may not be appropriate for a man of more a more distinctive standing and vintage. The gym-to-office look that’s been embraced by the world’s biggest fashion houses is a trend best served for younger men. Unless you’re at the gym, jogger pants, elastic bands on pants and other athletic-inspired clothing outside of the gym screams of a man trying too hard to hold on.


Lay off the trends

It’s best for a man to be considered stylish as opposed to fashionable – and there is a difference. Style is timeless and the all time great men of style typically didn’t cling to whatever the latest fashion trend was at the time. Fashionable means wearing the trends of the day and at times can result in significant cringing when looking back at old photos.

untucked and rolled up cuff
Yes many 40-ish have this look. Don’t be one of them.

That said, trends can be specific to men in their 40’s. For example, a trend that was recently widely adopted was the look for men between 40 to 60 to wear jeans and an untucked button down shirt with the cuffs rolled up once to reveal a different pattern or colour. It became a uniform for men of this age at bars, parties and events all over North America. Whether you liked the look or not is up to you (and we certainly didn’t), but it conveyed a lack of individualism or natural style because it was the look of the day (or at least the look for this age of men for a few years). Avoiding trends also means that focusing on essentials and what specifically works for you means you’ll get more out of your wardrobe investment in that you don’t have to donate clothes that are no longer on trend.


Don’t follow everyone else

Through this guide, we want to convey tips for dressing in your 40’s, but like any guide, you have to make this work for who you are and your own personal style. Although you want to dress for your age, you also want to make sure that you don’t look like a clone of all other men your age. Go to any large corporation that still maintains more professional dress code, and chances are you’ll see the uniform of a dark, charcoal wool suit, black suit, white shirt and tie. This can be a great look, but don’t get caught up in following suit (pardon the expression) that others set. This applies at work, when you’re out socially or anywhere else in life.

Follow the style that makes you feel good and reflects who you are – and if that means you stand out – then take that as a compliment.


Details matter

As your style matures and you focus on a wardrobe that works for you, it’s important to pay attention to your accessories. This means it’s a good time to add a heirloom watch to your family, such as a Rolex Submariner, an Omega Seamaster, Breitling Navitimer or a Tag Hueur Carrera.

omega seamaster 300 watch
Omega Seamaster 300

No disrespect to ZZ Top, but cheap sunglasses aren’t going to cut it anymore. Invest in sunglasses you won’t have to replace every other year or ones you’ll take care of so they won’t get lost. You can’t go wrong with the classics, including Ray Ban Wayfarers or Aviators, Persol 714’s or Vintage Carrera Aviators. You can also find great newer designs, including Tom Ford Bradbury sunglasses or Gucci Frame Acetate Sunglasses.

Persol 714 sunglasses
Persol 714 sunglasses – Steve McQueen style

Finally, we all carry a little baggage in our 40’s, but now when you carry a bag, it should be one of quality. Your bag is a statement in the workplace and while you travel and it’s important to make the right statement. It’s time to move past the nylon messenger bag and carry a bag for grown ups, particularly one made of quality leather. A great option is the Bottega Veneta Nero Intrecciato Calf briefcase.

The same can be said when you travel. Nothing says spring break like packing duffel bags or a mix of suitcases. Invest in good matching suitcases, such as a brand like Tumi, and they will last you for many years and convey that you’re a man of the world.


Essential guide to style quick hits

Before we move on to some specific items we’d recommend for a man in his 40’s, a few random tips for your best decade:

  1. Age gracefully. Avoid dyeing your hair, cosmetic surgery or other ways of cheating the ageing process. The more you accept ageing and make it work for your style, the better you’ll look and the better people will look at you.
  2. Take care of yourself. Stay in shape by exercising and eating right. Clothes look best on a body that is lean a toned. Besides, it’s good for you and you’re still a young man. You’re in your 40’s, not your 80’s.
  3. Regularly purge your closet. We like the idea of doing it twice a year – once at the beginning of spring and once at the beginning of fall. If you haven’t worn an item since the last time you purged, consider donating it to charity.
  4. Don’t forget swimwear. The long boardshorts aren’t off limits, but they’re also not great – particularly with a loud design. We like swim trunks with a 6-7″ inseam by brands like Orlebar Brown or Saturdays NYC.


40-something men doing it right


Idris Elba


David Bekham


Ryan Reynolds


Michael Fassbender


Jude Law