The search for the perfect wardrobe is one that men who value style will have to work through for their entire lives as styles and trends change. As men age, so too do their tastes evolve as each stage of life brings a new sense of direction that comes with change.
Whether you are just beginning to build your wardrobe as a young man in his 20s, or looking to add the perfect pieces to accentuate an already curated collection, here are the style points that men should take into consideration at each stage of life that will equate to sartorial excellence as you age.
Keep reading and learn everything that you need to know about dressing appropriately for your age, in your 20s, 30s, 40s and beyond.
How to Dress in Your Twenties (20s)
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Men in their 20s are just beginning their ascent into manhood, and this is the first time where you have the complete freedom to research and hone your personal style.
During this time in your life, you will possibly be in the best shape, which will give you more options to choose from when it comes to your wardrobe. At this age, collect pieces that will serve as the cornerstones to your wardrobe and will last across several decades.
Although this may be a time in your life where you have the loftiest of goals, this is typically a time where your budget will be smaller, making it all the more important to select pieces that are presentable as well as dependable.
Staple Pieces for Your 20s
To start, every man should own a few clean and classic, basic t-shirts, at least one pair of nice chinos, great fitting jeans, some slim tapered joggers, at least 2 pairs of quality shoes and a few casual sneakers, a well-tailored, contemporary suit and a few accessories that are versatile enough to wear with most of your wardrobe.
If there was ever a time to experiment with your wardrobe, now is the best time to do it, so have no fear in playing around with colors and patterns now because at this age, you can get away with just about anything sartorially. Once you reach your 30s and upwards, this will not be the case, so enjoy it now!
Find Your Style Strengths & Take Style Risks
Apart from the physical advantages that come with youth, there is an art form to knowing when to experiment with fashion and when to rely on classic options; knowledge that comes with age. A man in his early 20s is far less inclined to know quality suits compared to a man in his 30s.
Nonetheless, take this opportunity to find your strengths and learn how to minimize your fashion weaknesses in this first adult decade of your life. The more risks you take now, the fewer issues you will encounter as you enter other eras of your life as you find your singular style.
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Style Considerations for Your 20s
The advantage of youth will absolve many a young man of sartorial sins, but your mission should still be to minimize those where you navigate your personal road to good style.
Don’t confuse people with your style, instead, consume them with it. The following guidelines will ensure that you navigate your 20s in a fashion-forward way:
Themes and Schemes
Even in your 20s, one shouldn’t dress aimlessly, so when you are putting together an outfit, have an idea in mind about the direction of your outfit and what message you are trying to convey.
This is an essential element for men no matter his age, but if you adopt this mantra now, it won’t have to be introduced and reinforced as you get older.
There are many looks you can attempt from preppy and grunge, to minimalist style, hipster and beyond. If your final look resembles a few of these simultaneously, go back to the drawing board and rearrange some items.
Hipster Grunge Master
Switch It Up
You have the rest of your life to work a tailored look that fits you to a T. In your 20s, it’s all about experimentation and finding the image you would like for yourself.
So, although you may feel most comfortable in jeans and a tee, now is the time to think outside the box and venture towards new things that you won’t have the luxury of being able to pull off in your later years.
I implore you to dress outside your comfort zone, play around with themes, mix things up! Vary your look day to day and don’t fall into the trap of being pigeonholed into a look before you are ready to fully claim it.
That means you have the liberty to go from skater boy to prep school, slashed jeans to chinos and back again. This is the decade to go all out as you have nothing to lose!
Learning the Art of Accessories
Your 20s are the perfect time to recognize the power of accessories and how they can definitively elevate an outfit. An eye-catching accessory can elicit a message that can speak volumes, making it clear to everyone you encounter without saying a word.
Whether you choose a casual outfit or something more upscale, sharp accessories and being able to properly curate them is a tool that every man should possess, preferably as soon as possible.
Owning the Casual Cachet
Now that you’ve entered adulthood, the start of honing your personal style begins in earnest, so feel free to curate the styles that veer towards the persona you wish to emulate as a burgeoning man of distinction. Take these tips to cultivate your casual cache.
A Trusted Pair of Jeans
You can never go wrong with a pair of jeans in your wardrobe, and in your 20s, you can get away with a large percentage of your closet consisting of a variety of jeans.
But no matter how many pairs you indulge in, you should always have a fitted pair that can be dressed up with a blazer or a nice button-up shirt. Opt for darker colors like dark wash denim for more formal occasions rather than lighter hues.
Even in your 20s, you should have a couple of blazers, and to start out, add a light-colored blazer for less formal occasions and a darker one for more formal events to have your bases covered. You can incrementally add more hues as you age and hone your personal style.
Embrace the Color Wheel
Although you should not wear them all simultaneously, introducing color into your repertoire can be applied to all of your clothes from socks and tees, to trousers and jackets.
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Of course, you should coordinate them properly so they don’t clash, but that also can be learned over time.
There should be at least one (preferably more) pair of chinos in any man’s closet at any given time. Chinos work for men of any size and age, plus offer tremendous versatility as they can be paired with a polo shirt for a dressed down casual event or with a long sleeved button-down for more formal events.
Accessories Make the Man
Accessories are an integral part of a man’s wardrobe and should not be taken lightly or overlooked if elevated fashion is your style destination. Be a made man with these tips to lock in a great look.
You should have at least two – one brown and one black. After you’ve covered the basics, you can add as many other hues as you like.
Start with muted darker tones, and then branch out towards patterned and brightly colored socks that can accentuate an outfit or a pair of shoes.
Most men have more than a few pairs of shoes in their closet, but there are some basics that must be covered first. That includes a trusted pair of sneakers, leather brogues for formal attire and sandals for the warmer months.
Getting Down to Business
There are several mini-transitions in your 20s, with many men graduating from high school, then later university, and then out into the corporate world. All of these monumental transitions typically require new dress codes and serve as the beginning of a man’s true journey into style.
In the business world, that means owning at least a suit or two as you will probably endure a round of interviews for employment. Here are the keys to properly rocking a suit and joining the gentleman’s club.
It’s All About the Fit
Men just starting out on their sartorial journey will soon learn that ready-to-wear suits are oversized and will have to be tailored in order to fit properly, especially on smaller frames. When it comes to formal clothing, proper sizing is imperative and separates the men from the boys.
After all, FIT IS KING! Shop for your trousers and jackets at companies that offer in-house adjustments and this is the perfect time to audition a tailor before deciding on one that you can trust with all your purchased apparel.
The Power of Simplicity
Young men who are just starting to assemble their wardrobes may not have all the answers and that is perfectly acceptable as you will be on a learning curve in the beginning. But in the initial stages, the basic styles are classic and consist of a two-button, single-breasted business suit in a navy.
And of course, you can’t go wrong with a navy bomber jacket either. Don’t forget to add a few white or light colored collared dress shirts, a few conservative neckties and a pair of Oxfords. Once you’ve gotten the essentials out of the way, you can expand your wardrobe to include three-piece and pinstriped suits in other colors.
Dress Up, Not Down
In your 20s, it’s all about making an impression, many of which may last you an entire lifetime. As such, being over prepared is the best way to ensure that you stay ahead of the pack and not fall by the wayside.
When you’re not sure about the dress code for a particular occasion, wear a suit coming in a level dress above what is expected. In the worst case scenario, you can always ditch the tie and jacket.
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How to Dress in Your Thirties (30s)
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Congratulations are in order if you have graduated to the next phase of life. If you were feeling unsure about your choices in life during your 20s—your 30s represent the time to do away with the components that misfired and incorporate the things that elevated your personal sense of style.
With the 20s all about experimentation and going for broke, by the time you reach your 30s, you should have a fairly good idea about what looks best for your frame and lifestyle.
Your 30s also mark another transition in your life as you may be at another level in your career or perhaps even starting a family. This means that you will have less time to invest in scouring for clothes as in previous years, so knowing what works and what doesn’t translates into time and energy saved.
Style Considerations for Your 30s
If your 20s were about making an impression, then your 30s are about cementing relationships and nurturing them in order to elevate to the next level. As such, looking your best around the clock will be even more essential than ever before.
Of course, you will still need jeans and trainers as part of your wardrobe, but more than likely, suits and blazers will become even more integral to your overall look and this is the first decade where you start to give back to yourself.
Personal grooming should always be a priority no matter what age you are, but in your 20s, it is far easier to get away with scruffy beards, man buns and unruly hair in public settings. By the time you hit your 30s, these fashion faux pas should be a thing of the past to present a more refined overall aesthetic.
The following tips will ensure that your 30s take everything up a notch.
Assembling Your Labels
This is the time in your life to curate the brands that are destined to become your personal favorites. Once you are in your 30s, you should be able to narrow down your selections in less time and know which labels you can depend on to provide you with quality apparel year after year, season after season.
These core shops will inevitably become the staples where you can have your most essential style elements taken care of as hassle-free as possible.
Get Suited and Booted
You’re more than likely going to need more than just one measly suit in your 30s, so use this decade to invest in a few more options that encompass a broader color scheme, with black, navy and grey suits providing the bare minimum.
Once those have been procured, broaden your wardrobe with bolder colors and patterns that can be worn during specific times and seasons of the year.
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You should also select trousers and blazers that are versatile enough to be layered with your premium denim, chinos and v-neck tees. By now, you should have a trusted tailor at your disposal to produce the refined look you are searching for.
Selecting Standout Pieces
If you made the right style decisions in your 20s and stocked up on the basic wardrobe pieces every man needs, then your 30s is the pivotal time to invest in those items that are classic, beautifully made, and make you look your absolute best.
Set aside the funds to pay for these once and they will remain as part of your closet for life. In your 30s, quality really should be the name of the game and your objective, when curating new pieces into your wardrobe.
There should be premium accessories working their way into your wardrobe by your 30s that ideally will last a lifetime. Aside from owning a versatile trench coat and proper umbrella, accessories should include cufflinks, leather wallets, silk ties, leather bags, hats and high-quality chukka boots.
The Less Is More Mantra
As you come into your own style-wise, your 30s mark a turning point in your sartorial ‘career’ as this will be one of the first stages where you will begin decluttering your wardrobe to find the gems that will carry on into a new decade.
A golden rule that should not be overlooked during this time is quality over quantity. Now is the time to make a conscious effort in steering clear of trends and fads to cultivate a style and presence that is all your own. That includes narrowing down the fabric types (see our summer fabric guide) that work best for your physique as well as selecting a signature scent that people will begin to associate with your presence.
The balancing act to curating amazing style begins in earnest during this decade, so take it seriously and it will pay off in the long run.
How to Dress in Your Forties (40s+)
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Now with a firm two decades of manhood under your belt, you’ll likely enter your 40s with an elevated sense of accomplishment and yet eager for the next stage to begin. With so many years of experience under your belt constructing your wardrobe, this could be the start of truly placing a definitive stamp on your style.
Now that you have curated, collected, and incorporated the best looks for your persona and agenda, here are the guidelines to ensure that you maintain what you have already learned and amplify the areas that will take you to the highest echelons of debonair gentlemen.
Style Considerations for Your 40s & Beyond
The Wardrobe Edit
Even the best dressed men encounter a few fashion faux pas over the years, and the 40s present the perfect time to take inventory of what you have accumulated over the years and decide if it is still worthy of your closet or if it needs to be discarded to make room for better pieces.
Also take this time to renovate the place you actually store your wardrobe as well by investing in fabric suit bags, wooden coat hangers and plastic boxes for our growing collection of essential shoes.
By the age of 40, you should have a very good idea of the styles that suit your body type and exactly how you like your clothes tailored.
One of the quintessential elements that separates the men from the boys is access to a great tailor, which means you should already have one you trust at your disposal for any types of alterations you may need.
Athleisurewear is a trend that is here to stay, and men of all ages should have some presentable sportswear that is versatile enough for the gym and fashionable enough for the streets.
Make a conscious effort to select athletic apparel that’s slightly a cut above standard fare, opting for muted colors and jumpers that include pieces from brands that are known for properly producing the look. A few athleisurewear brands worth checking out are Twillory, Public Rec, Vuori and Lululemon.
Bling It Up
By now, you may already have a few watches in rotation, but in your 40s, you have carte blanche to significantly add to the number if you are so inclined.
If you have not done so by now, don’t hesitate to treat yourself to a premium watch or bracelet that subtly features your preferred precious metals. Go ahead. You’ve earned it! And if you have a lovely lady in your life, you’ll be ready to accompany her in tea party attire too.
The Trouser Trade-Up
Wearing jeans or not is a decision that every man must make, but one point worth noting is that if you decide to keep them as a mainstay, they should be the best quality possible, not to mention tailored.
As for proper trousers, your 40s are the time to expand your selection of chinos, linen pants and slacks with more colors thrown into the mix now that you know your personal style points. Cover all your bases and you’ll never have trepidation over your trousers again.
The workplace in your 40s is the time when promotions ramp up and presentations become a more integral part of the routine, which means that you should be fine-tuning your office look to make the type of impressions that will make the difference and help you stand out. Don’t just have one great suit at this age. Have an arsenal.
Dressed to Impress
Those experimental hairstyles of your 20s should be a thing of the distant past by now, with your 40s including cuts that suit both the shape of your face as well as your hair type. This is the perfect time in your life to have a personal barber or two that needs little to no explanation to enhance your look.
Making it to your 40s is a blessing and with this era should come a bit of resilience, moxie and understated confidence that lets everyone know that you’ve arrived, survived and are now ready to thrive!
You’ve survived a few missteps, but now you are at the beginning of cruise control mode, which means you don’t have to try too hard. Sidestep that mid-life crisis and remind yourself that you have paid enough dues to be expressive and savvy. Prove that getting old can equate to getting even cooler.
Final Style Considerations
It is important to know when to seize the perfect opportunity to nurture your style, by mixing it up until you find those that are well-suited to your preferred aesthetic and persona.
From patterns to prints, signature ties and classic watches, these are the decades that will prime you for a course towards sartorial excellence in the coming years of your life. By the time you reach your 40s and especially as you enter your 50s, your wardrobe is sure to be as chic and confident as you are.
And there you have it, our definitive guide to dressing up and out in your twenties, thirties, forties and beyond. I hope that you were able to get some value from this article and that you find yourself aligning on the appropriate attire—wherever you are on your sartorial journey, no matter the age.
Are you dressing appropriately for your age?
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