5 Things Jack Sparrow Taught Me About Fashion & Makeup

The first time I laid eyes on Captain Jack Sparrow I was completely flabbergasted.   I didn’t know what to think.

The dreadlocks. The gold teeth. The goatee.  The leather hat.  The hair trinkets.  The coat.  The eye makeup.  The individual elements looked… ridiculous. (If you need a reminder, check this out.)

Yet, somehow… he was strangely confident.  He had a certain swagger.   A sexiness.

He was untouchable.  He was perfect.

This came up during a conversation a friend and I were having about the upcoming release of Pirates of the Caribbean: On Stranger Tides.  She couldn’t believe it when I suggested that Jack was – in a way – a fashion icon.

She doesn’t think so.

I would argue he is because he has taught us some important lessons about style, including the following:

1. Everyone should own a kohl eye pencil

Jack took a page out of Cleopatra’s book and lined his eyes in black kohl. Look at how those babies POP.  So sexy.  If it’s good enough for the two of them, it’s good enough for me!  (My recommendation: MAC eye kohl)

2. Think outside the box.

Find new ways to use the pieces you have lying around your closet.  Here, Jack wears one scarf as a headband and another as a belt/sash.  Why not try belting a scarf?  Or using it as a turban?  If you are a DIYer, consider refashioning some of the things you are bored with – it’s the easiest way to breathe life into them!

3.  What’s better than 1 ring?  2 rings!  3 rings!  4 rings!

It’s no secret that I am addicted to rings (I can’t wait to share my latest purchase with you all when I receive it!).  Jack is a man after my own heart with the bling he wears.  You don’t have to limit yourself to 1 or 2 statement rings.  The more the merrier!  But if you go big on the rings, you will probably want to keep your other jewelry minimal.

4. Your hair is what truly completes your look.

One of the beliefs my mother instilled in me at a young age is that your hair is your most important accessory.  It doesn’t matter if you are rocking the latest Tom Ford design and some killer Louboutin’s – if your hair is a wreck it will ruin the whole look.  Jack is very proud of his rockstar dreadlocks and adds some extra glam with his hair trinkets.  Figure out what works for you and make your hair the most important part of your look.  You do wear it every day, don’t you?

5. Romantic + Edgy = WIN!

When you find a particular style that suits you and your personality, work it.  Jack has mastered romantic rockstar chic.  He masterfully melds silks and lace with leather, fur, mega-bling and dreads.  And his makeup?  There are no words.  Truly.


I regret nothing, ever.” – Captain Jack Sparrow

I love Captain Jack Sparrow’s no apologies approach to fashion.  He is his own man and owns his look.  All others are cheap imitations.

So, what do you think?  Jack Sparrow – fashion icon or no?

What surprising individual has taught you some lessons about style?


All images courtesy of Google Images and used for entertainment purposes only. The character of Jack Sparrow is the property of Disney.

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  • K October 28, 2012, 7:31 PM

    Jack definitely has style. My 8-year-old son is going as Jack Sparrow for Halloween and told me in no uncertain terms that he NEEDS eyeliner. Now I have to go find him some costume bling.

  • Amanda March 26, 2012, 4:30 PM

    I love the guy and have been lucky enough to see him in action whilst filming the last Pirate…film in Cornwall.

  • Recca March 25, 2012, 12:57 PM

    Pirates! Ha Ha! I love Captain Jack Sparrow so much that in every year’s costume event, I would always pick the pirates attire.

  • Anna February 14, 2012, 1:12 PM

    Oh my Goodness! that was amazingly hilarious but also true he totally owns his look and no one can even come close to touching it! fashion icon all the way!

    Check out my blog! snippetsofjack.blogspot.com

  • Clara January 22, 2012, 12:21 AM

    Thanks for a great laugh! there is always truth in humor and in fashion.

  • jk January 19, 2012, 2:06 PM

    I totally agree . In fact I use kohl eye pencil myself, it really brings attention to your eyes . I am also the person that mix and match stuff in my closet. It all depends on the taste you have got .

  • Kyla November 27, 2011, 9:14 AM

    Who doesn’t love Jack Sparrow? He’s one incredible pirate. And I agree completely, he’s most definitely a fashion icon. Who could forget the odd choices he made that came together so well and made him indescribably sexy? There’s a reason he’s many a girl’s fantasy come to life.

    Thanks for the great post outlining just why we love him! How could I resist an article that promised pictures of Jack Sparrow? Have a great day!

  • Dolly September 28, 2011, 5:49 PM

    Hahahah, I love this!!! Romantic+Edgy indeed!!! That eye-linered pretty boy will always have my heart <3

  • Tanya Wells July 14, 2011, 2:47 PM

    I am a Johnny Depp fan. Costumes and make up worn by him are really exceptional. His expressions and poses speak for themselves

  • Freya Grace July 3, 2011, 4:56 PM

    Jack Sparrow is a fashion icon, certainly, but in the same way that Marilyn Monroe (and Manson, for that matter) and Pamela Anderson are. There’s is the kind of unforgettable style only to be imitated at halloween parties for decades to come!

  • ruxandra June 15, 2011, 10:15 AM

    i love him he i so funny and adorable

  • Fashion Photographer June 12, 2011, 3:31 PM

    hell, if I could get away with (and pull off) looking like him every day I would do it in a heartbeat!

  • FashionIndie June 8, 2011, 12:17 PM

    ahhh Jack Sparrow has a special place in my fashion heart. He does pull everything off with such sexiness and your tips are perfect!

  • miranda May 26, 2011, 2:40 PM

    hello:) I loved this post sooo much, so I featured it on my tiny blog here: http://ladyemmy.wordpress.com/2011/05/25/wednesday-thoughts/ I hope you dont mind! Let me kno either way:)

  • Anika http://byanika.com May 25, 2011, 2:28 AM

    I think he is HOT and so are YOU! I was smiling and nodding and laughing trough your whole post, I love love love it, and I subscribe to all of the five points! This is one of the best reads ever. You are so talented my dear, soulful, funny, with georgeous locks and a heart of gold. I adore you! I am off to tweet and share this post everywhere! Hope you are sleeping thight still, I am having my morning coffee at work. Hugs!

  • Miss Rockwell May 24, 2011, 2:40 PM

    This is soooo fun. I would’ve never thought to associate makeup and fashion with Jack Sparrow. Way to go!!


  • Fashion Limbo May 24, 2011, 8:21 AM

    hehehhehe, this is a really funny post, and yes, he is a complete fashion icon, no doubt about that 😉

  • Clare Turner May 24, 2011, 8:19 AM

    Pirates and rock stars rule! Jack seems to have influenced his fashion sense when he’s not playing him too – good taste!

  • Lauren Nicole May 23, 2011, 7:55 PM

    You’re hilarious and have an awesome personality! This is one of the funniest fashion posts I’ve read in a while.

    kudos for the eye pencil. I always have jack sparrow eyes. lol

  • Anna May 23, 2011, 2:43 PM

    I laughed so much with this post!!!
    You’d have to add, that one must know how to use kohl…as you see, Jack Sparrow looks sexy and not like a panda bear 😛

  • Mode Plus May 23, 2011, 11:16 AM

    Such an individual approach to what a fashion icon is. I enjoyed this post. Witty but also informative. No wonder it was retweeted last week so many times. I’m going for Jack Sparrow as a fashion icon.

  • Colleen May 23, 2011, 10:43 AM

    Wow all I have to say is this is purely amazing.

  • Katie May 23, 2011, 1:32 AM

    Love it! He’s definitely an icon and the kohl pencil is truly a must.

  • Kenzi May 22, 2011, 10:11 PM

    I absolutely LOVE this!! It’s so true and its such a cute post!!! 🙂 Very original & I would have never thought about it that way.

    I love Jack Sparrow!!

    Thanks for stopping by my blog!!


  • Erika @ Health and Happiness in LA May 22, 2011, 3:42 PM

    I LOVE this post! I totally agree with all your lessons and I agree, Captain Jack is a fashion icon!

  • GRIT & GLAMOUR May 22, 2011, 1:48 PM

    Haaaa! LOVE this! LOVE!

    So glad you passed on the eyeliner recommendation. Been looking for a nice, soft kohl. This very day I took a match to my pencil so I could soften it for a nice black, inside-the-eye line. Looking for a pencil that will do that, sans flame!

    And yeah, I’ve been feeling the ring love, too. But you already knew that. 😉

  • Alex Matoshko May 21, 2011, 1:18 PM

    I cannot agree more – Jack totally is a fashion icon! In fact, when the “Pirates” first came out, I was so obsessed with his persona, I tried to dress like him for Halloween 😀 I love his rock’n’roll style and attitude – after all, that’s what made the movie interesting in the first place! Who wants another common pirate…
    By the way you convinced me – gonna get me a black kohl! I mean I do like myself with softer colors – I usually use brown eye pencil and eyeliner, but for special occasions – black could be perfect!
    P.S.: Just followed you, dear! If you have a moment, please check out my blog and follow if you like.

  • bestofbklyn May 21, 2011, 11:45 AM

    This absolutely cracked me up!

  • Erin May 21, 2011, 10:41 AM

    This was such a good idea. I’ve secretly been using Jack as a style icon for years. He and I have a lot in common, including our dreadlocks and love of rum! Nice work, found this via IFB by the way.

  • Debbie Baker Burns May 20, 2011, 9:55 PM

    Going to see Jack tomorrow…can’t wait! He does have a lovely look, doesn’t he? Last year at Vacation Bible School our theme was pirates and I lined my eyes pretty good with black liner and one of the ladies told me I should wear it more often, so I think you’re on to something here!

  • Carrie May 20, 2011, 7:00 PM

    Wow…that was absolutely incredible. I also believe we can learn great things from Captain Jack Sparrow. Can’t wait to see the movie! Yes, your mom is so right. Hair is so important as an accessory. Trying to find the right style can be a challenge. Thank you for this fun and clever post! Really enjoyed it!
    XO Carrie

  • Martina Lynne :: The Life Academic May 20, 2011, 6:23 PM

    Hi-lare. Seriously, I would never have thought to do a post like this, but you’re so right! I think we should start to consider Mr. Sparrow a model in life on the whole: rum is good, adventures are fun, never go less than 100% into anything, and when in doubt make a fool of yourself.

  • Sarah May 20, 2011, 4:55 PM

    Awesome, awesome, awesome. You truly can find inspiration for what you wear and how you look everywhere.

  • Cassie May 20, 2011, 3:45 PM

    YES! I have always loved his look in these movies! And I definitely agree with his (your) tips – definitely applicable. I somehow never thought about belting a scarf – I’m definitely going to try that out this weekend.

  • Ria May 20, 2011, 3:14 PM

    Just stumbled upon your blog on the Link a la Mode on IFB and gotta admit I was a bit apprehensive when I saw the blog title, but amazed at how right you are! The Captain certainly knows how to rock pirate/rebel chic completely fearlessly.
    You’ve definitely gained a follower 🙂 xoxo

  • Katherine May 20, 2011, 2:17 PM

    I never thought of him this way but YOU ARE ABSOLUTELY RIGHT!

    He is just perfect, ca vie?


  • academiaemily May 20, 2011, 2:10 PM

    Thank you for helping me put a finger on yet another reason I love Captain Jack. The man has style! Great post 🙂

  • Kimi May 20, 2011, 12:05 PM

    This post is hilarious!! And so right on. Jack Sparrow IS a fashion icon, no question. I would also agree that there’s a certain sexiness to his devil-may-care attitude and confident swagger, and we could all stand to take a few pages from his play book.

    Thanks for commenting on my blog. I appreciate your honest and kind feedback. The points you raised in your original post really are helpful, and I read it with interest when I first stumbled across it weeks ago. I read everything I can find about how to improve my blog, but the sulky teenager inside of me has a hard time admitting it sometimes. I’m really quite uncertain when it comes to blogging, since I’m still pretty new at it, which is why I’m reluctant to air peeves. You know, glass houses, stones, that sort of thing.

  • Julian May 20, 2011, 10:40 AM

    This is hilarious! And the points you made are actually really useful!

    Great post!

  • Oh to Be a Muse May 20, 2011, 10:29 AM

    hahaha! what an awesome post. truly, this made me laugh, and it also happens to be entirely accurate! kohl eyeliner, rings…so fashionable! 🙂

  • vonnie May 20, 2011, 10:10 AM

    omg, this made me LOL so much! “a scrap of lovely lace repurposed as a bracelet” indeed…..I LOVE this post and you have my deep bow of kudos for it 😀

  • empress May 20, 2011, 8:15 AM

    lmaooo this is hilarious, Jack Sparrow is a diva!

  • Victoria May 20, 2011, 7:41 AM

    I don’t know where you come up with the inspiration for these amazing posts! This is brilliant, I love my kohl pencil, it’s a must have in every girls make-up bag I think xxx

  • Fabienne Jach May 20, 2011, 12:57 AM

    YES! That was awesome, “imagine the possibilities”. He is an icon and you cracked me up the whole time that I was reading it. Love your style and humor:)
    xo, f
    The House in the Clouds

  • M @StyleSizzle May 19, 2011, 6:25 PM

    Love.This.Post. Seriously. I always thought Jack Sparrow was sexy, even if it’s in a you-know-he-totally-smells way. But honestly, great post. Totally love it. Especially loving how you deconstructed the way he blended romance and rock star chic–so true!

  • For Those About To Shop May 19, 2011, 2:17 PM

    You read Copyblogger, don’t you darling? Me, too, and I was wondering how to use this idea of fascination and usefulness together. You have pulled it off expertly and beautifully. Congratulations on a fantastic post. And “I regret nothing, ever” is my new mantra, starting today.

  • Bella Q May 19, 2011, 12:42 PM

    You convinced me. I didn’t think you could do it. But yes, Jack Sparrow is a fashion icon. And I’m off to Walgreen’s to buy me some kohl eye liner.

  • Kristin May 19, 2011, 12:30 PM

    DUDE…I knew I loved you. I am most obsessed with Captain Jack and have expressed such on la blog multiple times. People must think I’m a nut! Haha. LOVE, love, love this post. And I clearly need to get a kohl eyeliner. My friend did a guest post today on the smoky eye look and she sang the praises of kohl too!

  • Madison May 19, 2011, 11:51 AM

    Actually, I totally agree, especially (loving) the way you broke it down-to-size here. I have had a kohl type of eye pencil from the first time I was digging in my mother’s makeup bag as a little girl! This has such humour…
    How appropriate this quote is & I agree, “I regret nothing, ever” I love that B!

  • Heidi/The Closet Coach May 19, 2011, 11:21 AM

    LOL, yes and yes!

    Plus it doesn’t hurt that Cap’n Jack Sparrow is played by Johnny Depp, nom nom nom.

    I think I may have written the opposite of this post two years ago; it’s about why Keith Richards is *not* a style icon! (http://www.closet-coach.com/2009/06/16/keith-richards-is-a-guitar-hero-not-a-style-icon/)

  • perdita May 19, 2011, 3:22 AM

    Love it! Those 5 are SO true!

    My unusual fashion guide is Joy from My Name Is Earle: grown women CAN wear hair accessories. Lots. 😉

  • THE-LOUDMOUTH May 19, 2011, 2:36 AM

    This is amazing. Seriously, you are so smart & talented with your humor! This must be submitted to LINK LOVE!!!

  • Heather Fonseca May 19, 2011, 12:52 AM

    I’m starting to sound like a broken record but GREAT POST! Maybe the best fashion blog post EVER WRITTEN! I love it! And I totally agree with you. Captain Jack is a fashion icon. I have always loved the pirate “look”, even when I was a kid, though I’ve never worn it myself.

  • Elle May 19, 2011, 12:26 AM

    Thanks for the laugh B, I really needed it today. And this is an amazing post! I love you-in the pas t I actually did a fashion inspiration post on The Joker.

  • Ashe @ Dramatis Personae May 18, 2011, 11:14 PM

    This is the most hysterical and awesome version of this type of post I’ve seen.

  • Elaine May 18, 2011, 9:07 PM

    hahahaha this post was awesome

  • vanessa May 18, 2011, 8:58 PM

    What do I think? Fashion icon.. yes. This post was pretty awesome, and really well written. Who woudl think you could learn so much from a pirate.

  • Misfit Sarah May 18, 2011, 8:41 PM

    GREAT post! The other two elements that I think make this look so perfect are confidence and humour! He doesn’t care what anyone thinks plus he doesn’t take himself too seriously… and that is sexy as all get out!

    Sarah xxx

  • MADMSL May 18, 2011, 6:27 PM

    Haha, love this post. Haven’t been by in a while,
    but who caqn resist Captain Jack Sparrow, and yes you’re right.
    He has got a certain swagger!

  • Jenmarie May 18, 2011, 6:04 PM

    I NEVER thought he looked ridiculous but I did think that he would act ridiculous, ha! I love all the points you made about his wardrobe. This list is just absolutely perfect. I’ve always loved the things that make him Captain Jack Sparrow. The kohl, THAT hat, his walk. He’s kind of perfect in a weird sort of way.

  • Bonnie May 18, 2011, 4:50 PM

    Kohl eye pencils are a MUST.
    Jack Sparrow convinced me of this fact.

    Twitter: @GlamKitten88

  • Jamillah May 18, 2011, 4:42 PM

    AH!!! As if I could not love you more!!! This post had me smiling as I scrolled!

    I adore Jack Sparrow!!! Johnny Depp was the 1st boy I fell in love with…so I’m bias, but I agree with all your points! And Mr. Sparrow totally has one-upped me in some of his fashion! Kohl eye, I have yet to master…shame face.

    I love all the captions in your last pic! Billowy shirt!! Yes please!!! Edgy knee-high boots! Um yes to that too!!

    Such a fun post!!! Thanks B!

  • MJ May 18, 2011, 4:35 PM

    I saw the title of this and I just HAD to read this!!

    Can I first say that the visuals just had me cracking up!! Everything you said was very true. Your hair does play an important part in your look (and your swagg!) 🙂

  • Alexis of NorthOnHarper May 18, 2011, 4:20 PM

    I could not stop laughing…. yet somehow, invaluable advice (esp the eyeliner)!!!!!

    Nicely done!

  • Treacle May 18, 2011, 3:59 PM

    Ha! This made me laugh. Awesome work, and perfect timing (of course!). 😉

  • Tanvi May 18, 2011, 3:56 PM


    ♡ from © tanvii.com

  • Tanvi May 18, 2011, 4:13 PM

    P.S. Having used Kohl liners (Kajal) everyday … since I was like, one day old … so from experience I was suggest Benefit’s BADgal eyeliner! 🙂

  • Rocquelle May 18, 2011, 3:56 PM

    Ha! Love this! I need to go buy a MAC kohl liner like yesterday!

    I have learned from Ronald McDonald that color is great, and color blocking is even better!

  • Courtney May 18, 2011, 3:46 PM

    OMG B I LOVE THIS. I would’ve never thought I’d be reading about Jack Sparrow’s fashion style.

  • Fashnlvr May 18, 2011, 3:44 PM

    OMG!! I love this post!! AND I absolutely adore Johnny Depp! Jack Sparrow? More please!! I agree he is a fashion icon and very sexy!

  • Arash Mazinani May 18, 2011, 3:39 PM

    Ha ha I love this post I just watched the first film a couple of days ago. I love his style and swagger and I think you did a good job of highlighting practical things you can learn from jack sparrow.


  • Meg May 18, 2011, 3:34 PM

    I love this post! I definitely think he is a style icon, just because he is a fictional character doesn’t mean he can’t be… carrie bradshaw was one!! 🙂
    I also agree with number 1….i ALWAYS wear eyeliner, doesn’t matter if I have other makeup on or not, as long as I have my eyes done, everythings good!!
    I think romantic rockstar is the perfect way to describe his look!

  • Casee Marie May 18, 2011, 3:31 PM

    Dying. Captain Jack Sparrow’s a total fashion icon – and a total stud muffin, I mean come on. (I should add that when the first movie came out a sixteen year-old Casee Marie found herself utterly obsessed – I have a copy of the script and everything. Yeah.)

    He definitely revolutionized the kohl pencil. I don’t think I’ve ever known a fictional character to create the sort of lasting impact on pop culture that he did – in all aspects. Although I do have to say I think I credit Phoebe from Friends as my original multi-ring inspiration. She and Jack have some oddly similar style sense, come to think of it.

    Did I mention this was a brilliant post, and exactly what I needed? I’ve been feeling too serious about blogging lately and this was the perfect bit of escapism.

  • Eva May 18, 2011, 3:25 PM

    Oh my, I suspect this will go viral. 🙂

  • Heidi May 18, 2011, 3:12 PM

    LOOooovvvvinggg this post!! The Kohl rimmed eyes are super sexy! Romantic Rockstar chic is a great way to sum up his look!! Love Capin’ Jack! <3 <3 <3 H

  • Rambling Heather May 18, 2011, 3:11 PM

    LOVE this. Too funny and true 🙂

  • Kirstin Marie May 18, 2011, 3:09 PM

    I would have to agree with you! There is definitely something about him that is edgy and sexy. It’s a certain appeal that the costuming/overall fashion & style of Jack Sparrow that just screams for your attention, but not in a bad way. I LOVE khol eye pencil. I use it every day on my water line. Another fun use for it – If you draw on your lids with it, you can smudge it into an awesome super quick smoky eye. Two looks in one product? I’ll take it!

    I love this post. So much so, that I tweeted it. <3