Get Started with Classic Male Style. . .

 

Today's post responds to a question posed by a reader in Chile, Alfonso (26), who wrote to me in Spanish (Muchas gracias, Alfonso, y mucho gusto!) a week or so ago.  And while my own Spanish is very rusty at this point, I believe the gist of his email was the perennial question "How does someone interested in classic male style and attire get started?" Especially in our overly casual era.

Well, many articles, books, blogs, and vlogs have been written on the subject, so the following advice echos what you might find elsewhere.  My own answer is to start small, make informed decisions, and purchase fewer items but spend enough for quality attire that will last a long time.  If money is tight, consider charity shops and watch for online sales.  

Older  family members too might be able to help if you are similar in height and size.  Keep in mind that most tailors can handle a few basic alterations that will make your clothes look and feel like they were made just for you.

Ok, let's begin in earnest.

Start with maybe a navy sports jacket or blazer and add a tweed sports jacket when you can.  Both look equally good with jeans for a casual look but will instantly elevate your appearance.  I opted for this look often myself when I was a graduate student teaching undergraduates, and it helped me stand out just a bit from them as the authority figure at the front of the classroom.  

Of course, I looked much younger 25+ years ago.  But I digress!

Add a pair or two of khaki chinos in different shades -- tan, stone, or olive green -- with the possible later addition of a pair or two of creased wool dress pants, maybe one in a mid- or lighter gray and one in charcoal.  Again, these can be easily paired with a blazer and sports jacket for a more casual look, or dressed up with the addition of a necktie for a dinner out with that special someone, a presentation in the office, or a more formal event.

Speaking of neckties, no need to go overboard here.  Two or three -- tied using the four-in-hand knot (small, elegant, and slightly asymmetric)  -- will serve you well in almost every situation.  Maybe a couple of repp stripe models and a solid knit wool or silk tie for a more casual look.  You can venture into foulards and the odd 'critter' tie or two later.  Again, no need to spend a lot of money on brand new things.  

Decent quality silk and wool neckties are easy to find in many thrift and charity shops.  Or watch for sales online.  And again, older male family members might be able to assist with the donation of a few things from their own closets that they no longer need.  It never hurts to ask when you are starting your own sartorial journey.

For shirts, begin with three button-down collar dress models sized to your specific neck and sleeve length, maybe  one in light blue (looks good with most skin tones), another in white, and a third with a faint pattern or stripes.  This particular collar style looks equally good with or without a necktie for those more casual times and environments in which we all find ourselves in 2026.  You can add additional shirts and (possibly) collar styles later.

For shoes, stick with leather and make sure to match your belt to them as near as possible.  If money is scarce, limit yourself to a single pair for now.  Choose a mid-brown or reddish brown (so called Oxblood) pair of lace-up oxfords with rounded toes.  Spend as much as you can here since good quality welted leather shoes, with routine care and maintenance, will last for years.  

Keep your investment in good shape with routine shines in the appropriate color with the addition and use of cedar shoe trees every evening when you remove them for the day.  As soon as you can, add a more casual pair of so called 'penny loafers,' again in a mid- or reddish brown.  For more formal occasions, add a pair of black lace-up oxfords later but you can probably get by without these at least early on.

For socks, keep it very simple and go with navy or charcoal to-the-knee wool dress socks for everything.  It just works.  For a more casual occasion or look, you can venture into subtle patterns, motifs, and Argyll.  The latter looks great with heavier corduroy trousers during the colder months, but avoid so called "statement socks," which are hard to combine in a pleasing way with most classic male attire.  

More generally, strive to keep things subtle and harmonious when it comes to your overall appearance.  I don't always manage to achieve that balance myself, but it is good to keep the following point in mind, attributed to the late Coco Chanel.  "Look at yourself carefully in the mirror before leaving the house for the day and remove one item."  Admittedly, I may be misquoting slightly here, but you grasp the point.   

Fine, but what about a suit?

Well, every man should have at least one hanging in his wardrobe although, to be honest,  you can probably get by without that item in 2026.  Unless you are in a profession like law, banking, finance, or government in a large city.  When you can, though, add a two-piece wool suit in a mid-gray, charcoal, or navy (but avoid black) to your wardrobe.  Again, shop carefully in thrift or charity establishments, query older male relatives who may have a few things hanging in their closets that they no longer need or wear, and watch for online sales.  

Remember that good fit is everything, so know your own physical measurements and take your suit to a tailor for a few minor alterations to customize it to your particular dimensions.  It's well worth the time and money spent. Do be sure to rehang your suit (and all other clothing items) on a wooden hanger at the end of the day to preserve its shape and help it air out after wearing.  Try too not to wear the same item day after day but give each combination of clothing time for small wrinkles and creases from wear to smooth out simply by virtue of hanging them up as soon as you remove them.

If you are anxious about standing out like a sore thumb, or making a big change at once, relax.  Do it bit by bit ("Poco a poco" as they say in the Yucatan) over the course of a year or two.  Before you know it, you'll just become part of the scenery as those around you become used to your (gradually) improved appearance.  Start small with the addition of that navy or tweed sports jacket mentioned above with a tucked in shirt and jeans worn with a belt.  You'll look great in almost any environment: the classroom, the more casual office or business setting, and certainly for an evening out on the town.  

And if anyone asks "What are you so dressed up for?"  Just smile and reply "I'm celebrating being alive!" Leave it at that and then move on with your day or evening.  It's that easy.  No additional explanation is necessary.  Life is too short to worry about what others might think or say.  It took me a long time to figure that out, so avoid making the same mistake.

There you are Alfonso!  I hope my advice might help you (and others) begin your own sartorial journey with quiet confidence in the knowledge that you'll look more than presentable -- even fabulous -- anywhere you go.  One thing I find in my own life is that others, both men and especially women, will appreciate your efforts to present yourself well even when they say nothing.  Their appreciation of a well dressed man who pays attention to details will be apparent, however, through how they interact with you.  It's hard to miss.  

Who knows?  You might even hear the occasional compliment from a passerby.  It happens.  And while never necessary, it's always nice when someone shares a few kind words about your appearance. Clothes along don't make the man, of course, but how we present ourselves to the rest of the world is more important than many care to admit.

Last, you might be very interested in checking out The Chap's Guide Youtube channel too.  Ash is very knowledgeable when it comes to men's style and grooming, and he addresses many of the questions men of every age ask about dressing intentionally in the 21st century.  I hope that helps and enjoy the weekend!

Kind Regards,

Heinz-Ulrich