6 Timeless Men’s Styles

Justin Confalone February 19, 2019 Lifestyle

Style has gone through some major changes over the years, for better or worse. We’re past the days of poofy hair and bright fabrics, and the joy of the early 2000s punk uprising is long behind us. In the 2000s alone style has gone through some crazy changes, men’s style has gone from bright patterned jackets and graphic tees to a mod culture uprising (I’m talking caps, and British pop inspired, see here for reference). In the 2010s we’ve gone from a weird cashmere phase to fedoras, then from fedoras to bright sneakers, and in 2019 we’ve arrived at streetwear, possibly the most interesting current trend (which may be on the way out soon). There’s no need to cite an article for this one, we’ve all seen the designer brands, relaxed fit, and stunning (if not a bit ambitious) color/ material combinations. Recently (I’m talking 2010 onwards) clean-cut clothing has also made an impact on fashion culture.

From where we are now, nobody really knows where fashion will go next, with streetwear and clean-cut being the two supporting pillars of modern men’s fashion, one is bound to shape the next style trend. And while these kinds of trends will always come and go, some pieces of men’s fashion will survive even the most experimental changes.

Greaser Style (Inspired)

If you’ve ever watched “The Outsiders” this fashion should come right to your mind. In its simplest form, this style consists of three things: Blue jeans, a tight white shirt and a black leather jacket to bring it all together. This is one of the few styles on this list that can be taken directly from the 50s and still pass as stylish today. As for shoes, a pair of Converse is the classic look, but pairing this look with leather boots (black or dark brown) can also tie it together well; bonus points if you pair it with a black or brown leather belt. While the look itself is really minimal, so much of this look is popular on its own. Let’s break the essentials of this style down.

The Basic T-Shirt

Starting at the base of the greaser look we have the simple t-shirt. This is as basic as fashion gets, but when properly fitting, is one of the most eye-catching items a man can own. They tend to be cheap so stock up on them in your white’s and blacks, maybe throwing in some colors and greys as well. Try to go for a fit that doesn’t squeeze, but just hugs your biceps for maximum appeal.

The Jacket

A good leather jacket can be paired with almost anything up top, but for the bottom half of the outfit, try to stick with jeans (or sweatpants if you are daring enough to dive into streetwear.) Leather jackets come in a range of colors, but for the best look, stick to brown or black leather as your base, and buy new colors if you feel the need. According to this article, leather generates a feeling of excitement and adventure, two very attractive and rewarding things in a guy.

Blue Jeans
There really isn’t much to tell you about jeans, there’s a reason nearly every guy owns a pair. Blue is the tried and true classic and can pair well with pretty much anything. If you’re wearing jeans… just go crazy! Jeans also make a great addition to our next timeless look.

Lumberjack Style

Okay, I know lumberjacks don’t always wear flannels but the aesthetic is there so we’re gonna stick with it. This style generally has four parts. Jeans, undershirt, boots and of course the flannel. This look gives a feeling of refined ruggedness and is one of the most masculine styles a man can rock. It can even be part of a sleeker, less rugged look if paired with the right things. Let’s break it down.

The Jeans

Unlike the greaser look, jeans, when paired with a flannel, can be much more than just black or blue. While the classic feel might be lost if you go too wild, have some fun with the color combos you can make. I’d personally recommend light wash jeans here, but the ambitious man can even sub out the jeans for a pair of chinos.

The Undershirt

While you can keep the undershirt something as clean and simple as white/black and still look great, textures and graphics also work. If you want to go for maximum style, sub your undershirt for a henley.

The Boots

To maximize the impact of the lumberjack look, a solid pair of boots (leather or suede) is a must. Outside of the flannel look, dark brown or black boots can pair with any color combination or most outfits in general. Boots can also be subbed out for a pair of white trainers if you want to take the fashion risk.

The Flannel

The humble flannel, not only a key piece to the lumberjack look but an essential to any guy’s wardrobe. They come in all types of colors but the classic red and white is a hard combination to beat. Start with a red/white flannel and throw in some new colors when you get comfortable with the look!

Denim on Denim

This might be a bit of personal bias but denim on denim is one of the modern man’s best looks. There is a lot to say about a fabric that was made more than a century ago and still is stylish today. Wearing a blue top on black selvage jeans is a personal favorite of mine, but any combination of colors and shades can look good as long as you follow a few rules. One, wearing the same shade of denim is a massive style risk, and it almost never pays off. Ditch the double indigo look for something a little more varied, at the very least keep the shades of blue slightly different to avoid the onesie feel. The only exception to this rule is black on black denim (since every guy looks good in all black) and for the ambitious, white on white denim (but layer on different colors). Two, keep the denim unbuttoned if you’re wearing an undershirt. Let’s break the style down further.

The Shoes/Boots

Footwear in a denim on denim look is completely up to you; just a couple of things to keep in mind. Try to match the footwear to the pants (or some color on your body) and keep them to basic colors (white, black, grey, brown). As an alternative, a pair of white trainers work well with most basic colors.

The Undershirt

While showing off an undershirt is technically optional in a denim on denim style, interesting patterns and certain colors can generate synergy in your outfit. According to an online color guide, the best outfits have common ground on the color wheel, using different colored undershirts can help tie this look together. Denim can either look clean cut or can be a bit more streetwear if you combine it with something like athletic pants.

Suit and Tie (For Work)

While the suits have gotten a bit slimmer and fewer people are wearing hats, the old-school suit and tie look still is amazing today. There really isn’t much to say about this look because it speaks for itself; clean shoes, pants that match the jacket and/or vest, undershirt, belt, and a tie make up the outfit. Even the button up on its own can be a style.

The Button Up (For Casual Wear)

Generally, you’ll want to wear a button up under a suit, and while that’s common knowledge, the not-so-obvious knowledge is that the button up itself can be a look. Without the suit, a button-up can be worn completely unbuttoned if you treat it like a flannel, this works best if combined with an interesting undershirt.

The Preppy Look

While it’s changed throughout the generations, the essence of the preppy look has remained the same since it’s early 1900s roots. This look covers a pretty broad area of fashion ranging anywhere from polo shirts to dress shirts up top, but the thing that ties this look together is the sweater. Crew or V-neck, the sweater and button up combo is the core of the preppy look. The key is to layer the sweatshirt so that the collar just peeking through enough. Combine this with jeans or chinos, and tie everything together with a pair of white sneakers, loafers or boots to maximize style.  This look tends to be brighter with more simple and standout colors shaping the feel of it, once you master the synergy, this is a style that should be worn with the pride of the Ivy League students who invented it.

All Black

It doesn’t matter where or when it is, a guy dressed head to toe in black will always look damn good. The color has been a staple of men’s fashion for ages because it adds a sleek, sophisticated and mysterious flair to the person wearing it. Even more important is that having solid black up and down your body forces eyes to wander down, making someone who would normally walk by you unknowingly take in your entire style. According to this study, black is the best color to show confidence and intelligence, as well as being the most desired color by women. All black is a little vaguer than most styles here, but the look can be something as simple as black jeans, boots and a black henley, or a combination of layers of black in different shades and textures. If you want to ditch the solid black look, opt. for a darker grey or any color that keeps the outfit monochrome. Because matching black on black is natural, this style instantly gives you a more put together and matching look than its alternatives (especially if you are newer to fashion and just learning to match well.) Know that you know the bare basics, what’s stopping you from giving these styles a try?

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