The Best Bad Boy Around

I have to admit, I’ve been meaning to write for some time, but I’ve been lacking inspiration. I really should have just looked in front of my face. With the new revival coming up and a coworker beginning her first viewing of the series, both of which spurred my own rewatch, I have had Gilmore Girls on the brain lately.

Now I know Gilmore Girls may not be terribly familiar to this audience, but here’s what you need to know for now. Jess is the Best.

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Jess, played by Milo Ventimiglia, is the quintessential intellectual bad boy; he’s got a troubled past, doesn’t like small talk, and is more likely to sass than not, but he also gets his life together in a big way. He’s the best bad boy around.

While Jess is immediately recognizable as the resident rebel with his James Dean glare, black leather jacket, and carefully coifed hair…the rest of his wardrobe is pretty…normal.

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There’s a lot of dark colors, ribbed sweaters, and so, so many layers. But even a yellow/gold coat can work for a bad boy with the right amount of snark and disregard. But he plays up his assets. The neutral colors don’t pull focus away from his face. Pushed up sleeves, tight-ish sweaters, and bulky watches draw attention to his arms.

His hair changes length through out the series, but always remains artfully disheveled. When it’s short, he uses product. When it’s long, he keeps it out of his face.

And while his jeans might be a little loose by modern trends, and some of his shirts scream mid-2000s, a lot of it is quality basics.

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Mimic Jess with hoodies under leather jackets, or maybe even different types of sweaters. Trade the classic mid-2000s look of a long-sleeved shirt under a short-sleeved shirt for a black or white v-neck.

Jess Mariano’s wardrobe matured as he did, and I can’t wait to see where his life and wardrobe have gone in the past eight years.

#JessistheBest #TeamJess

 

To nail the literary part of this intellectual bad boy’s look, keep an eye out for a literary gents post that I am desperately trying to complete.

As always, please send requests for things you’d like to see!

 

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Subtlety is Key

“Menswear is about subtlety. It’s about good style and good taste” -Alexander McQueen

There’s a reason we have so often warned against clothes, particularly t-shirts, with obvious logos, brand names, or photos on them. Even if it is a well-know, well-respected, or frankly, expensive brand, having a logo branded across your chest looks a little less than sophisticated.

Also this

Truth from Ian Bohen

is a problem most easily hidden with plain, nondescript shirts.

But, occasionally, a shirt is just too good to pass up or let go. So here’s what you do when that is the case:

Note: Funny phrases are rarely as clever as you think they are. Avoid trying to wear your humor on your literal sleeve.

Aim for black and white or a neutral and one other color. This keeps even a busy image simple and doesn’t draw the eye to quiet the same degree.

Another way to tone down the message/focus on the shirt is to layer. Use another shirt or jacket to cover part of the design, making it interesting, but not the focus.

subtle logos

There are times where it is okay to try to be witty – and that is when you are unabashedly, but subtlely, reping yourself. This Stark Direwolf/Iron Man shirt is clever, but it is infinitely better on Kit Harrington and Robert Downey Jr. It’s an extra level of inside joke. Most people can’t really get this, but you know, it was worth mentioning.

Too Clever

And my personal favorite is this hat:

Blake.

Bob Morely wearing this hat at Comic Con is a clear reference to his character, Bellamy Blake. But, the hat is vague enough that it could literally refer to anything. I want one – do I love the retired tennis player James Blake, or the Romantic poet William Blake, the character Bellamy Blake? You don’t know*! I love it.

*It’s a trick question, the answer is all three. (Although full disclosure: my favorite Romantic poet is John Keats. I would gladly accept a hat that read “Keats.”

Blast from the Past

The Inspiration 

“I look just like Buddy Holly, Oh-oh and you’re Mary Tyler Moore” -Weezer

buddyholly

Buddy Holly was a musician and songwriter who pioneered a lot of many of the hallmarks of modern rock and pop music. Although Holly died in 1959 at only 22, he remains immortalized in numerous songs, movies, musicals, and books about his music and influence. Critic Bruce Eder described him as “the single most influential creative force in early rock and roll.”

The Modern Translation

Modern Buddy Holly

Style-wise Buddy Holly is the perfect embodiment of the late-50s good-guy rocker. He’s clean cut, well-kept, and charmingly genuine looking.

Tailored suits with floppy bow ties, shawl-neck cardigans, button-ups and ties, and knitwear tees are classic callbacks, that have a new life in modern fashion. Thick-rimmed glasses paired with any of these looks are the real kicker.

John Mayer is known as almost anything but a “good-guy” rocker, but his outfit at the (otherwise dull) 2015 Grammy Awards invoked classic Holly. The blue jacket, glasses, well-coiffed hair, and pink guitar were down right swoon-worthy. Especially the pink guitar.

While John Mayer may have nailed the look this time, check out consistently Holly-esque looks on New Zealand musician Willy Moon.

The Inspiration

“‘Cause you got that James Dean daydream look in your eyes.” -Taylor Swift

James Dean

James Dean was an actor that turned into a bonafide icon. He is the poster child for teenage angst and rebelling without a cause. Like Holly, Dean died young in a tragic crash. He was only 24 in 1955 and, again like Holly, has been immortalized in film, biographies, and as the bad boy of everyone’s dreams.

The Modern Translation

Modern James Dean

James Dean is angst and apathy embodied. He’s a little bit dangerous, does what he wants, and is somehow above judgement and vain.

Moto-style black leather jackets, tight white t-shirts, slim black jeans, and sunglasses make up the modern James Dean look. Largely monochrome, or at least neutral, this guy would blend in if he didn’t exude so much cool. While James Dean’s hair was usually pretty done, as per the era, the modern version can either be a slick pompodour or disheveled and a little longer.

Jamie Campbell-Bower owns the pretty, bad boy that couldn’t care if his shirt has holes in it or not, but if you are looking for the whole James-Dean-reincarnated experience, check out Milo Ventimiglia as Jess Mariano in Gilmore Girls. He’s got the outfits, hair, and angst in droves.