New year, new clothes: expert advice to how to start a gentleman's wardrobe

Though the most common resolutions for the new year center around health, either physical or financial, it is well worth considering a resolution to improve your style.

If this is your first foray into the sartorial world, first of all welcome, it can appear confusing as phrases such as drape, Super 100s and correctness are bandied about in a way that, at first blush, is not dissimilar to the particulars of applied physics.

Fortunately, many of the well-dressed are more than willing to lend a helping hand to the interested.

We spoke with experts from both sides of the pond and they shared what advice they would give to someone taking advantage of the new year to start dressing well.

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Understand clothing as expression and language

The aesthetic improvement derived from dressing well is a valid reason to start but the true benefit is the internal joy that comes with it.

"That sense of feeling impeccably dressed and wearing something beautiful, and then the confidence that inspires you is, is very life changing, in some respects," Tom Chamberlin, editor-in-chief of The Rake, said. "It really does ratify what it is that you want, or you've always wanted to, present yourself as to the world."

Derek Guy, style writer at large and an X, formerly Twitter, celebrity, said that understanding how to execute that presentation can be improved by understanding what clothing says.

"It's helpful to understand clothing as cultural language," Guy said. "Just as there are many types of languages as English, Chinese, Spanish, French, German, whatever, there are many different aesthetics and learning an aesthetic is just like learning a cultural language."

A good place to begin an understanding of that cultural language is through film, a common starting point for those who look to improve the way they dress.

"Most people have a connection to a movie star or James Bond, the outfits of James Bond," Chamberlin said. "(It's) something where you feel, 'I feel like if I got that, or something close to that, then I will be expressing what I want to express about myself.'"

Guy said that developing style is at least a five-year process where there will inevitably be missteps along the way.

"The goal to keep in mind is to develop an emotional relationship with your clothes, find stuff that you love, wearing," Guys said. "On day one, there's going to be ton of mistakes. You're going to buy stuff that doesn't fit, and you're like, you're slowly developing your tastes and finding what works for you.

Even someone with as developed a style as Chamberlin, or more accurately because his style is developed, recognizes that not every garment is perfect for him.

"I got and probably still do get an awful lot wrong," Chamberlin said. "I think I'm quick to notice when it's wrong these days."

Focus on quality and maintain a reasonable pace

It would be easy to throw around money in an attempt to create an instantly fashionable set of clothes but it skips the important step of developing the personal aspects of style

Kirby Allison, the founder and star of his eponymous YouTube channel and store, said that investing in well-made garments over time will give you the versatility to eventually branch out.

Allison recommends, "focusing on quality and not quantity" and "being very strategic (with) your purchases and your acquisitions."

"As you're investing and acquiring these pieces for your wardrobe, try to withstand the impulse to go for the shiny, the loud, the interesting and the unusual, that inevitably, you're not able to wear that much or you might grow tired of and instead focus on foundational items that lend to the longevity of those pieces," Allison said.

While the word "classic" is tossed around frequently, there is a sound logic to focusing on pieces that can be used long enough to allow for memories to sink into the warp and weft of the fabric.

"Even if you have the means to (create a full wardrobe) I think it's really important to get acquainted with the basics and build from there," Chamberlin said. "It's a bit like backgammon, you build your board, you create a base of strength somewhere on the board, and you build on that."

A few practical points

The advice is echoed by author, journalist and highly regarded dresser Nicholas Foulkes who said, "buy the best you can."

Foulkes noted that stepping into the world of the well-dressed did not require a massive cash investment.

Though Foulkes has a wardrobe of garments made bespoke, primarily from tailor Terry Haste of Kent, Haste and Lachter, he described his sartorial start inheriting suits and purchasing vintage clothing in the 1970's as, "undergraduate courses before graduating into bespoke tailoring proper." 

"There's a feeling of having a garment that you've had for years, and it's very satisfying. Buying the best you can and having it last for years and maybe even outlast the wearer is perfect," Foulkes said.

One advantage of entering the world of men's style at the moment is that the pendulum has started its trip away from the Jim Moore-GQ era of ultra slim fits to something that allows for food and drink to be consumed.

"If you're still walking around in one of those tight little suits you're going to start looking like a dinosaur," G. Bruce Boyer, fashion editor for Town and Country and author of "Elegance", "Rebel Style" and his latest "Riffs: Random Reflections on Jazz, Blues, and Early Rock" said. "The whole silhouette of men's clothing has gotten easier and a bit larger. Suits are a bit easier fitting, trousers and sport jackets (as well)."

Boyer also noted that the flexibility of how the world dresses allows for creative use of formal pieces.

"For years and years and years, you didn't see an overcoat," Boyer said. "Now, you're starting to see them all over the place and it's not only a garment now that guy is wearing with a suit or something like that, but they're wearing them with jeans and a chunky turtleneck sweater or a cashmere watch cap and a scarf or something like that."

The journey of finding your style will be a process, as Guy noted, but having someone that can advise you along the way can help make it easier.

Find a company that is either local to you (or at least local in spirit), such as Junior’s of Philadelphia, J. Press in the Northeast or Sid Mashburn, and purchase something from them.

You’ll receive something more unique than you can at a department store and there is an opportunity to develop a relationship with a sales associate that can help build out a useful and sustainable wardrobe.