Timeless style is a term that gets thrown around constantly in forums and on blogs. Recently it’s reached peak saturation and a lot of the more cynical men in the #menswear community are starting to chafe at its mention. After all, timelessness is impossible to achieve in clothing. A suit from the 60’s would look out of place today, more so 100 years ago, and even more so 1000 years ago.

However, a timeless style is still a valid description and a worthwhile pursuit. The distinction needs to be made between a style that will always look fashionable or one that will always make the man look great.

To better illustrate the point:

Take a look at this photo of Rita Hayworth and Fred Astaire rehearsing a dance number. Astaire, one of the kings of the Golden Age of Hollywood, is undeniably well-dressed. There’s a great balance between Refined (hair, materials, cut) and Rakish (rolled sleeves, dark socks, exposed throat). A photo like this can bring about nostalgia from a time that many consider to be the pinnacle of entertainment.

However, if a man were to walk down the streets of any city today wearing this exact outfit, he would be seen as a caricature, not a well-dressed gentleman. The high waisted, full-cut, pleated trousers are about as far from current style sensibilities as one can get (which just means they’ll be all the rage at Pitti in three years). Redditors would tear the guy apart for wearing those dark socks, and the sashed belt looks affected to the point of being a joke. Clearly any man replicating this outfit in 2014 is wearing a costume, not dressing stylishly. Yet we look at this photo and still recognize Astaire for the sartorialist he was.

Here’s another example.

Both of these photos are from the 70’s (technically Redford’s is ’81 but it was still the era of 70’s style). On the left we see a tux that is obviously and recognizably from that era. It’s bad. The piping, massive lapels with a low gorge, ruffles everywhere, bell-bottomed slacks… I could go on but it’s fairly obvious that this is not a timeless look.

On the other hand, we have Robert Redford. Once again, there are some details that would be unwelcome at an awards show today. The trousers are fairly baggy, the bow tie is giant, and the length of the jacket is a bit excessive. However, this photo makes Redford look incredibly refined, masculine, and timeless. Even with the obviously 70’s-era hair, the photo still looks as great today as it would have upon its release.

So, why is it that both Astaire and Redford appear timeless when their styles are in context, but would look silly and outdated if those exact items of clothing were worn today? The key lies in two areas – avoiding anything overly trendy and focusing on clothing that draws attention to the man.

Both of these concepts have already been discussed at great length on this site, so they’re not entirely new ideas. But, their usage can be developed even further to help men attain that “timeless” look many of us are after.

As an experiment, I bet every reader can tell me with 100% accuracy which of the following photos I believe contain timeless style and which illustrate dead trends.

Again, all six of these would look ridiculous if worn today. However, the top three keep the viewers attention on the men, while the bottom three clearly demonstrate clothing that distracts.

Just remember that timelessness isn’t always the goal. In the example from the 70’s above, the kid on the left was attending his prom. He was much more concerned with looking great amongst his peers and probably trying to see how far he could get with the girl on his arm. He wasn’t planning on getting married, accepting an award, or representing a business. The whole purpose was simply to look cool (groovy?). It was both intentional and acceptable that his powder-blue tux stole the limelight from everything else about him that night – that’s what it was supposed to do.

With all of this in mind, I make and will continue to make recommendations that are certainly going to look silly in a decade or two. Sockless, overly high gorges on jacket lapels, etc. They all have their reasons, but their popularity will wax and wane as much as any other aspect of men’s clothing. As with any other concept in men’s clothing, the key to wearing something well is knowing the message a man wants to communicate and which clothing does so the most effectively.

image from City Home Collective

One of the most common refrains I hear about why most guys don’t dress better is that shopping is too frustrating and/or painful. While I get the sentiment and even laud the companies that attempt to make it easier, this is a stupid and invalid reason to dress poorly.

In fact, it’s a serious #firstworldproblem when men consider buying clothing to be a painful experience. I get that it’s uncomfortable; it sucks to feel like one has no idea what he’s doing, and our egos are damaged when we feel un or undereducated about a particular topic. But painful? Pain is having a home foreclosed on, going to war, or losing a child. Shopping may be frustrating, it may be humbling, but it shouldn’t ever be considered painful.

And even if it were, that doesn’t mean it needs to be avoided. I’m in a little bit of pain right now. After a brutal leg day with some new friends yesterday morning, I can barely walk up or down stairs, I resent the fact that my car is a manual instead of an automatic, and the fact that my daughter may drop something and ask me to pick it up fills me with dread. My friends told me tomorrow is going to be even worse. But, that pain is a great thing. It reminds me that I went hard yesterday, that I’m actively improving myself as a man, that I have a body capable of being pushed to the point that it feels pain and then recovers better and stronger.

I’m no masochist. I don’t enjoy pain for its own sake. But I also don’t think it’s the ultimate factor in deciding whether a given activity is worthwhile. Sometimes going to work is a pain. In fact, sometimes writing a post for the site is a pain. Being a father, son, husband, boyfriend, friend, mentor, student, boss, employee, or any other role in which we find ourselves can be painful. Doesn’t mean they’re not worth pursuing.

There’s really only one type of person who lets pain and its effects completely outweigh all of the other pros and cons of an activity or role – a child. And, as a father, it’s kind of a pain to have to teach my children that pain can sometimes be a good thing.

If a man wants to make building a wardrobe, looking for clothing, and improving his image a more manageable and enjoyable experience, there are a few things he can do.

First is to embrace the fact that it’s going to be a bit of work. How much work is dependent on the man, his current style, his style goals, and how hard he’s willing to work to get there. However, aesthetic inertia is the same as any other kind – getting the ball rolling requires a lot more effort, energy, and pain than keeping it moving.

The second thing he can do is to shop like a man instead of a woman. I’d venture a guess that one of the reasons most men find shopping so difficult is because it’s typically done with the women in their lives. Most women tend to browse, touch, try, and experience while they’re shopping. It’s great for them but that kind of attitude will drive the majority of men crazy. The solution is to treat wardrobe building like the mission it is. A man isn’t at the mall for the experience. He’s there to accomplish a predetermined goal. The amount of planning and hyper focus necessary will vary with each man, but knowing what he’s there for and specifically searching for clothing makes the experience more productive and more enjoyable. This doesn’t mean he doesn’t check for other items or even deviate from the course when presented with a better opportunity, it simply means he knows his purpose before venturing into a store.

Which brings us to the third suggestion. A man isn’t shopping, he’s wardrobe building. Whether he hires someone to teach him, reads through great internet sources, watches how-to videos, or even turns to physical books, wardrobe building is better accomplished when it’s learned with the help of an expert. Eventually the man will be able to stand on his own two metaphorical feet, but until he can, he saves himself (and his wallet) from a lot of unnecessary bumps and bruises by turning to someone who knows what he’s doing.

In the end, it doesn’t matter how enjoyable or difficult wardrobe building is, it’s a worthwhile endeavor that will immediately impact a man’s life and help encourage other improvements as well. Embracing the importance of it, and the ways to make it more manageable will help keep the discomfort of doing so a productive pain.

It’s an experience every man should have, and most of us probably will. There’s something different about flying into another city or even a different country when it’s done on business instead of vacation. Here’s what every man should bring along.

Navy Suit

Kind of a cheater move since it’s not really going to be packed. For the sake of dignified air travel and keeping his suit in top form, it’s best to wear this on the plane. Unless the flight is completely packed, most attendants are willing to hang up the jacket while in the air, allowing for a more comfortable ride and fewer wrinkles in the suit.

The reason for navy is because it’s easier to pair the jacket with some of the other items in his bag. A lot of men will want to go explore the city they’re in when they’re not on the clock and a blue blazer works great day or night.

White Button-Up Shirt

Appropriate for both business meetings and going out at night, a white shirt is a blank canvas that could honestly be worn every day of the trip without anyone noticing (as long as it doesn’t smell too bad). Most men shy away from white because they consider it boring, but it’s my go-to color whenever I have to make a shirt last as many days as possible.

Blue OCBD

While white is the king of versatility, a blue oxford cloth button down comes in a very close second. The OCBD is great while meeting with clients but casual enough it can be worn with shorts or even a pair of swim trunks when headed to the beach or hotel pool.

Loafers/Monk Straps

Which of these a man chooses will depend on the formality and overall feel of his business. However, if at all possible, both are better than lace ups for the simple fact that they make airport security a whole lot easier. I even leave the top strap of my monks unbuckled when I’m in the airport to make it simple to simply slide them off and back on, allowing me to get out of the hell hole that is the TSA as quickly as possible.

Chinos/Jeans

Even I don’t want to wear a suit all the time. Chinos will dress up more than a pair of jeans but both can be made fairly work appropriate when paired with the navy jacket, a tie, and one of the button-up shirts. They can also both be worn casually when off the clock and around town.

Underwear/Socks/Ties

While it’s obvious that these need to be included, it’s best to bring one pair more than the expected number of travel days. They take up minimal space, and one can never tell when he’ll have to throw on an extra pair or swap out one tie for another.

Dopp Kit

Should be fairly obvious how important one of these little guys is. I always try to remember to pack extra Q-tips and have found that the shampoo/conditioner/body wash bottles that are provided by most hotels are the perfect size to keep in my kit. They don’t take up too much space and fall within TSA regulations, meaning I can keep this in a carry-on bag rather than having to check it.

There are a ton of great companies who make some excellent dopp kits, but this cheap version from Target has been with me for seven years and thousands of miles.

Swim Trunks

There will always been some down time, and it’s crucial that it be taken advantage of. On my most recent trip to Guatemala, everything we did occurred in the same hotel. Being able to spend some time relaxing in the pool made it feel less confining and even a little bit like a vacation.

These trunks from Cabana e Fogo are the best pair I’ve ever owned. They’re aggressively short without coming close to banana hammock territory, all pockets zip closed, they have a convenient loop for sunglasses, and even come with a water proof bag in which they can be stuffed after a swim. That little bag made it easier to pack for the return trip home without having to worry about getting everything else in my bag wet or having to steel a garbage liner from the hotel.

Sunglasses

While unnecessary on the plane or in the office, a great pair of shades will help keep travel throughout the remainder of the trip comfortable. Stick with something classic and stylish like these Wayfarers.

Pajamas

Even if a man sleeps in the buff, pajamas are a necessity. I’d hate to have to throw on jeans and a button-up shirt as I was evacuating a building because some kid pulled the fire alarm. They may never be used, but they take up little space and it’s better to have them than not.

Passport Cover

Going international? There is something infinitely more deliberate and well-seasoned about using a passport cover. This beauty from Chester Mox doubles up as a wallet and fits perfectly into the inner breast pocket of a suit jacket – making it a stylish way to carry all of a man’s info and money without having to purchase a pick-pocket fanny pack. Simply keep the breast pocket buttoned shut when not in use.

Watch

This is another tip that’s especially helpful for international travelers. Many men will keep their phones turned off as a way to avoid international charges – leaving them reliant on some other method of telling the time.

Casual Shoes

What pair? Depends on the man, the job, and the location. For some it may be a pair of bucks, and for others it’s the loudest Nike’s available. The point is to have something extra that can give his feet and his dress shoes a break during off hours without confining him to his hotel room or the pool.

Hat

It takes up very little space in a weekend or carryon bag and can be used as both an intentional item or simply to help out in emergencies. My go-to for travel is a seasonal drivers cap. Something in linen for summer and a heavy wool in the winter.

Deck of Cards

I’m the kind of man whose brain always has to be doing multiple things. Most of the time this means browsing on my phone. However, there are times when a man needs to disconnect from the tech world, while still giving his hands something to do. Whenever I need to unwind but sitting still is driving me crazy, I’ll play a classic game of solitaire. It can be done in coffee shops, hotel rooms, and even airplanes.

Everything in here will fit into a standard-sized carryon bag and is great for business trips of four days or shorter. If going for longer, it’s time to check a bag and start to double up on the necessities like a suit, shirts, etc.

While many of my readers are from different countries, the bulk of you are from the States. Friday we’ll be celebrating our Independence Day. And, without diving too deeply into the politics of that name and its increasingly ironic significance, I still believe it is a day worth celebrating.

So here are some tips on what to wear, regardless of the archetype in which a man finds himself.

Rugged

The key to a Rugged style has always been function over form. Long jeans and heavy boots may not be the most comfortable in the heat of summer, but they protect a man out in the woods or on the back of a motorcycle. The patriotism in this style is more inherent in the US-made products and the uniquely American aesthetic as opposed to an overwhelming demonstration of the stars and stripes.

Refined

 

If there’s ever a time for a man to embrace his inner WASP, this is it. Old money knows how to dress down while still keeping things tastefully Refined. And, just because he may not live in the Hamptons, doesn’t mean the Refined man can’t embrace the aesthetics of those who do. This style is typified by an unapologetic embrace of all things red, white, and blue. Oh, and there’s no such thing as too much Brooks Brothers.

The double monks and more aggressive fits keep this updated, but everything else in this look would have fit in on the 4th in 1959 and probably will in 2059 as well.

Rakish

As a counter to the Refined taste, the Rake understands how to use trends to his advantage. This look is overly casual, but will still communicate intention and taste when all of the items fit as they’re supposed to. Rakes are comfortable being a bit underdressed from both a formality and modesty perspective, so keeping the shorts above the knee and going sockless is what will hold this look together.

As always, a man should dress to both who he is and to his audience. Finding the correct balance may involve incorporating two or even all three archetypes together.

Don’t know which style best suits you? Head on over to my Coaching page to learn how I can teach you your correct archetype and how to dress accordingly.