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For a lot of guys trying to dress well can be downright frustrating. Trying to figure out what is in style, where to buy it, how to match it with other items, make sense of what to wear in a situation – it is no surprise that it can be intimidating and stressful.
For this reason, budget-conscious menswear advocates including Primer often talk about certain essentials that act as a foundation for an up-and-coming wardrobe. Things like the oxford shirt, non-square toe dress shoes, and dark straight or slim denim all form a solid base to then build upon.
But what happens once you already have a solid base? Where do you go from there? There are a number of super-versatile items that can open up a slew of options, perfect for a modern man’s life. Here, we explore 11 of them.
To the uninitiated, it may look like a denim shirt. But chambray isn’t denim (it isn’t a twill fabric like denim, and has a 1×1 weft/warp structure known as the chambray structure) and it has a long, and storied history. Brought back to popularity by the likes of J.Crew and other rugged staple retailers a few years ago, chambray was first invented in Cambrai, France in the late 1500’s. The chambray shirt as we know it is more than 120 years old, and is the original working shirt. In fact, the concept of “blue-collar” originated because workers were wearing blue chambray shirts. It was also a part of the standard Navy uniform from 1901 to World War II, and was made iconic in the 50’s and 60’s by Hollywood leading men like Brando, Dean and McQueen.
But enough history: The chambray shirt is an essential because it is multi-purpose and masculine. You’ll be perfectly dressed whether trying to look sharp on a date, or just schlepping it to the bar to watch the game with your buds.
It’s almost neutral on the “dressiness” scale: It’s the perfect layering item because it enhances whatever you pair it with. Combine it with a sweater for a sharp, casual look, wear it plain with jeans or chinos, or even wear it casually with a suit.
The original features two buttoned chest pockets, though variations are common, and is available in other colors like gray and red.
How to Wear It:
- The Getup: Autumn Street Festival
- The Getup: 21st Century Off-site Employee
- The Getup: Chilly & Casual
- The Getup: Summer Casual
- The Getup: Summer Art Festival Date
- The Getup: First BBQ
- The Getup: Summer Date
Figuring out what to wear when you’re “going out” can be one of the hardest and most common style scenarios to decipher. You don’t want to be too dressed up because you’ll be out of place, hot, or square. You don’t want to be too casual because you’ll look plain, lazy and unrefined. The secret is playing with the details. A well put-together look will leave drastically different impressions with one simple change of footwear between boots like Red Wings or dress shoes like wingtips. One is rakish and outdoorsy, the other, refined and gentlemanly. All coming down to one single detail – not which pants, shirt, or sweater to wear – the thing that can most define your outfit is your choice in footwear.
Because of this, more design-forward sneakers like these black leather Converse Jack Purcell’s become a man’s wardrobe staple. Take the exact same outfit described above, and now instead of Red Wings or wingtips, we opt for black leather sneakers. What happens to the outfit? It ‘casualizes’ it but maintains its evening appropriateness in a way more standard sneakers can’t. Pair them with slim dark denim or even chinos or wool trousers to add edge while taking out the stuffiness.
What you’re looking for is a more refined sneaker; something beyond your typical canvas go-to’s and less athletic or brand-forward than the Nike Air Max or New Balances.
How to Wear It:
Non-blue Jeans / Casual Pants That Aren’t Jeans or Chinos
The normal trajectory for men buying pants is: Jeans, dress pants for work, and then chinos for a little style. Maybe he gets a little crazy and buys chinos that aren’t khaki. But there are other options, and they can open up a huge box of fresh options the other 3 staples can’t provide. Case-in-point: Jeans that aren’t blue or casual pants that aren’t jeans like corduroy.
We frequently enlist dark denim as a way of looking stylish but remaining casual. Combinations can include more dressy sweaters, sportcoats, and even ties. The mixture of dress and casual can create a very sharp look when done correctly. But sometimes, blue denim is just too standard-issue or casual.
Take for instance, this combo featuring red micro-wale corduroy, a wool sportcoat, and a tie. With blue jeans the outfit would be rugged à la J.Crew, but it loses its appropriateness for more professional situations. Paired with chinos, you’ll have a great looking ensemble but it’ll be straight on business casual, which may be too dressy or out of place for your destination.
The solution is a pair of red denim / corduroy like these from Gap. It maintains our level of casualness without having to dive as casual as regular jeans, and gives us a put-together look without having to dress up to chinos or wool pants. The same goes for corduroy. A pair of standard-wale brown corduroy pants would look amazing in this setup, without dressing it up, or dressing it down.
Does the idea of red pants scare you? It doesn’t have to: By incorporating very conservative options in the rest of the outfit, the red doesn’t feel flashy or out of place. That’s a good tip to remember – when wearing items that are a little more adventurous than you’re used to, begin by surrounding them with conservative counterparts.
How to Wear It:
- The Getup: Pumpkin Patch Hayride Date
- The Getup: Spring Wine Tasting
- The Getup: Getting It Done
- The Getup: On the Go
The Non-silk Tie
For some reason, smooth silk ties are the de facto go-to for boys as they grow into men and need neckwear. “Silk ties are professional and businessmen wear them.” That’s true, but businessmen also wear power shirts with contrasting collars and we don’t buy them as wardrobe foundations.
In fact, if we’re going to define a wardrobe staple as something that a man should buy before differing options because of its versatility, a non-silk tie is the way to go hands down.
As someone who does not work in a highly uniformed industry like law or finance, I can’t even tell you when the last time I wore a smooth silk tie was. If that sounds like you too, someone who wears a tie occasionally to the office, or rarely to weddings and events, your start should be options like wool, cotton, or knit.
Also, smooth silk ties are inherently formal. They’re hard to dress down or wear more casually such as with jeans and a sweater. However, the texture that a wool, cotton, or knit tie provides allows you to wear a tie while also dressing down. It creates a more “smart casual” look rather than business casual or professional, though these ties also look fantastic paired with khakis or a suit.
How to Wear It:
On the surface, most guys assume there are four levels of pants: jeans, chinos, khakis, dress pants, in order from most casual to most dressy. But there are other options tucked in-between these staples that allow you to diversify both your overall style and dressiness of a getup. Similar to our non-blue denim above, finding a pair of pants with texture can ground an otherwise dressy outfit, the same way a textured tie can reduce the dressiness of an ensemble.
Take for instance this Getup I did last year. Not one of the other 4 standard pant styles could achieve this balance of casual and dress the way these herringbone trousers do. Jeans, obviously more casual. Chinos, more casual and a more weekend appearance. Khakis and dress pants would both overdress the rest of the outfit, even though its very sharp and an option for a lot of not-so-casual destinations.
Just as with the tie, we’re looking for something that can bring a little texture to the party; maybe that’s with the material like with flannel trousers, or with the pattern like the herringbone ones above. Now imagine those pants with a dress shirt and tie – what do we have? A “smart casual” option appropriate for networking, a less-than-formal office, or even certain dating scenarios. All which would look too much like “I work in a bank” if paired with chinos or khakis.
Shawl Collar Cardigan
If you’ve been a reader of Primer for any length of time you probably read “shawl collar cardigan” and thought, “Geez man, just quit it with the darn shawl collar cardigans.” And I apologize for featuring them so frequently but I do so for a reason: It’s probably one of the most versatile layering items in my arsenal.
Much like the chambray shirt, the shawl collar cardigan is neutral on the dressy scale – it can dress up a henley, or dress down a shirt, tie, and trousers away from a sportcoat.
Why the shawl collar specifically? These sweaters tend to be of a heartier knit, closer to the fisherman’s cable knit sweater, than the smooth merino wool Mr. Rogers variety. The result is a rugged appeal, balanced with the sleek shawl collar most commonly found on tuxedos.
There’s literally nothing this sweater can’t do. Wear it casually to brunch with jeans and a henley, or dress it up with your nicest dress shirt and wool pants. Either way, you’ll look damn good.
How to Wear It:
- The Getup: Up and Autumn
- The Getup: Coffee Date
- The Getup: Summer Weekend Freedom
- The Getup: Casual Fall Weekend
Ah, the henley. Perhaps the most ruggedly masculine shirt in existence. The ruse is that fundamentally it’s just a t-shirt with some buttons (or a polo without a collar), but somehow those buttons create a look that is lightyears beyond what any normal long sleeve t-shirt can do. A perfect layering item like the shawl collar cardigan or chambray shirt (which look great all together, see above), the henley adds a bit of visual texture to any outift.
The henley is available in a variety of configurations, long sleeve, short sleeve, thermal, etc. Worn underneath a button-up shirt creates a sense of rugged Americana, bonus points if you roll up the button-up’s sleeves to reveal the henley’s sleeves underneath. But the henley looks sharp on its own also, paired with some dark denim and hearty boots, and you’ve got a super simple, handsome look that’s about as comfortable as they come.
How to Wear It:
- The Getup: A Great Night of Music
- The Getup: Slushcapades
- The Getup: Watching the Game at the Bar
- The Getup: A Full Saturday
Card Case or Money Clip
Women figured out ages ago that we don’t need to carry everything with us all the time. They have giant sacks for purses when they need all their stuff, but they also have minuscule clutches for an evening out. Our wallets are no different.
Heading out on a nice date? Why do you need your Costanza bi-fold with superfluous tag-alongs like your gym membership, Costco card, grocery store card, office keycard, and 5 charge cards. The reality is you don’t – and if you’re overcome with a sense of nakedness just thinking about it, let me assure you that goes away the first time you try it.
There are even health consequences to sitting on a thick wallet, which is common sense if your hips and back are constantly uneven while sitting.
There are tons of options out there, from the simple two-pocket number shown above, or a simple money clip that can easily hold some cash, credit cards and ID.
If you’ve done even light reading on men’s style then you’ve certainly heard that good style “is in the details”. Outside of proper fit, nailing small details is one of the biggest things separating the well-dressed from the “eh-it-looks-ok,-I-guess” dressed. Barron from Effortless Gent has touched on it, so has Joe at Dappered. But this detail is more than just about looking sharp, it’s about not embarrassing yourself.
Socks are underwear, but there are a lot of common situations where people will see them unlike our skivvies. Unfortunately we typically don’t put a lot of importance on them outside of being absent of holes (none of your socks have holes, right?), so we don’t like investing a lot of money in them. But just buying that 12 pack of black dress socks and wearing them all the time to everything is a little like just wearing white briefs all the time: In a word, boring. By opting for socks with more colors and patterns you’re immediately creating a sense of personality and a display of intentional style to all who get a peak at them. Details like these can be huge on dates, since a lack of care for your ratty black socks can easily be misconstrued for a lack of care for other details in your life.
That’s not to say you should go around wearing rainbow colored socks everywhere, there is a time and place for conservativeness as well as flash, but you can wear socks of a pattern or color while also being subtle.
And perhaps the best part of it is, you don’t have to drop a ton of money on them either. A little secret: Surplus department stores like Marshalls, Ross, Nordstrom Rack, and TJ Maxx are all great places to find huge deals on designer socks. Take for instance this mult-pack of Ralph Lauren Polo socks – only $10 at Marshalls. These will be perfect for jeans and sneakers, a date, or even a suit.
Did you know?
The difference between suede and nubuck is which side of the leather is being used: Suede from the inner side of the hide, nubuck from the outer. Because of this nubuck is tougher and more expensive, generally with a finer grain.
Just like pants, men’s shoes are seemingly bilateral, casual and dress. This makes the middle ground of dressed-well, not dressed-up hard to style for. Most times, we default to a boot in this scenario, since the brown leather is reminiscent of dress shoes, but its rugged design is more casual. One of the worst mistakes a guy can make, and ultimately make him look like he’s 45, is wearing casual jeans with dress shoes. In most cases, it just doesn’t work. Like trying to wear a suit jacket as a blazer…they’re designed differently and don’t look right.
There is a happy compromise however, the suede oxford. Affectionately referred to as “bucks” because they’re commonly made of nubuck (or buckskin back in the day), these oxford-style shoes feature a napped leather upper and, usually, a brick red rubber sole. Bucks were originally intended as tennis shoes, and the suede upper and colored sole create a shoe that is both casual and dressy, and the perfect option when dressing for an in-between style situation.
Pair them with almost anything, jeans, chinos – some even work with suits.
How to Wear It:
The chunky dive watches made popular by the likes of Rolex and Omega have dominated men’s watch designs for more than fifty years. Much like a good boot, these watches create a piece that is gentlemanly with a rugged aesthetic. They’re incredibly versatile, can be dressed up or down, with a suit or with a t-shirt, and will remain a smart investment and wardrobe essential for as long as men still wear watches on their wrists.
But there are other watch styles. Particularly in contrast to the visual details of a diver is a minimalist watch. These timepieces intentionally have very sparse designs, some even without numbers on the dial. This deliberate minimalism brings quite a different detail to an outfit, in a similar way that different shoes can completely alter a look.
The use of a minimalist watch can have multiple effects. First, in a more dressed up ensemble a thin, minimalist watch can appear more dressy and sleek. In a casual outfit, a minimalist watch can further enhance the intentional casualness by being less sporty and less cluttered.
These are just a few of my favorite essentials. Now over to you! Do you have other not-so-obvious style essentials to add to the list? Keep the conversation going in the comments!