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Can a Hawaiian shirt EVER look stylish?

July 12, 2012 By Beth | Heads up: Buying via our links may result in us getting a commission. Also, we take your privacy rights seriously. Head here to learn more.

Ask A Woman:  Hawaiian Shirts 101

If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it.  Beth is our source for the answers.  From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday.  And don’t worry, your identity will be protected too.  Click here to get to know Beth, then get in touch with her by sending your question to: askawoman@dappered.com

 

Beth,

I have a basic question for you: Can a guy wear a Hawaiian shirt and still be considered well dressed?  Is there any setting where this is OK?  I’m trying to understand where the line between “wacky uncle” and “summer casual” is drawn.

–  Pete
.

Hi Pete,

The short answer to your question is that no one is going to consider a man in a Hawaiian shirt well-dressed.  They’re kitschy!  They’re colorful!  They have huge flowers on them!  Chunk wore one during the Truffle Shuffle!  It’s not exactly a dignified look.  But that doesn’t mean that you can’t wear one.  Though I love classic style, I also love eclectic elements incorporated–in moderation–into a wardrobe.  Are Hawaiian shirts my favorite?  No, but I also don’t want to see everyone walking around wearing the same thing–boring!  I realize this column, and Dappered at large, have been dedicated to classic, elegant style, but the more questions I get from readers, the more I realize that the best part of style is seeing what other people come up with, especially if it’s different from your own aesthetic.  If I insist that all of you wear pressed pants and slim fit button downs and navy blazers day in and day out, we’ll all die from boredom.  Boo!  It’s the kilt-wearer and the ascot-mascot who make fashion fun.  So I’m going to give you some pointers on wearing a Hawaiian shirt in case you decide Frank Sinatra-be-damned, you’re giving this look a whirl.

The wide scope of the the Hawaiian shirt.  Moving left to right: Seriously? –> As a heart attack

Style in this particular arena is tricky in that it works if it is intentional, but not if it isn’t.  Gotta love a double negative.  Here’s an example that might illustrate my point: ripped jeans.  Woman A is wearing light blue jeans whose waist rests midway between her armpits and belly button.  The butt of the jeans is saggy, the crotch of the jeans is too tight.  The jeans are a bit shredded around the knees and thighs, and there is evidence that this woman does oil changes in her spare time.  Woman B is wearing very dark blue jeans whose waist rests just below her belly button. The butt of the jeans is form fitting, the crotch of the jeans is smooth and flat.  The jeans are a bit shredded around the knees and thighs, but are otherwise spotless.  Both women are wearing ripped jeans, but one is wearing them because she doesn’t care, and the other is wearing them because she does.

This is how you approach tricky style quandaries like the Hawaiian shirt.  It needs to look like you meant to wear it, not like you dug it out of Frank Costanza’s attic.  This means it should be in good condition, and it should fit appropriately.  The Hawaiian shirt is cut to be worn a bit bigger and baggier, so try on several different sizes besides your normal in order to get a fit you feel comfortable with.  Who knows, maybe you’ll be a pioneer in the slim fitting Hawaiian shirt.

As you mentioned, setting for this look is crucial.  Backyard barbecues, pool parties, walks along the beach–are you seeing a trend here?  Warm weather only, casual setting only, outdoor activities only.  Wintertime, your wedding anniversary, dinner out–don’t you dare.  If you do, I’ll sense your transgression in my bones and then I’ll have no choice but to hunt you down and shame you.  With the cone of shame, naturally.

-Beth

Got a question for Beth? Send them to: askawoman@dappered.com

Filed Under: Clothing Tagged With: Ask A Woman, cool hawaiian shirts, Hawaiian Shirt, how to wear a hawaiian shirt, ripped jeans

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Comments

  1. Butch_Zee says

    July 12, 2012 at 4:45 AM

    It’s stylish with the Ferrari 308.

  2. Mike N says

    July 12, 2012 at 6:06 AM

    Well… anything is stylish with a Ferrari 308

  3. Farhan says

    July 12, 2012 at 6:41 AM

    It doesn’t hurt hat woman B is Kate Beckinsale.

  4. Ryan N. says

    July 12, 2012 at 7:02 AM

    Yes. Brad Pitt in Fight Club.

  5. Scott says

    July 12, 2012 at 7:07 AM

    There are some really nice vintage silk designs that are a bit more subdued that look really cool. But as Beth said, setting is everything. Last time I wore it, I think I was in Maui going out to dinner.

  6. Drew says

    July 12, 2012 at 7:57 AM

    I’d beg the differ on the notion that Hawaiian shirts cannot be considered well-dress…well at least in Hawaii. Are they on par with a well-tailored suit? Absolutely not, but it still has its place. It’s certainly all about perspective and the appropriate situation, as Beth mentioned. In Hawaii you’ll see the overwhelming majority of business men wear them to work and 80-90% of males (often including the wedding party) wear them at weddings. Being born and raised in Hawaii, I can tell you that our ‘idea’ of Aloha shirts (as they’re called) are much different than what is perceived by the rest of the World and popular media (ie the examples above). It’s really not so much about flashy/flamboyant colors with obnoxious floral prints. Luke warm and cool tones with subtle print are usually par for the course.

    While it’s certainly a niche that’s appropriate any day of the week/year round in Hawaii, finding the appropriate time or venue and having an open mind (not wearing it just to be ‘that guy’) in the States may be a bit more challenging. Of course, receptiveness will also vary with location – Palm Beach, FL vs. Flint, MI.

  7. Loki says

    July 12, 2012 at 10:06 AM

    I think it needs to be NOT faded. Those bright colors work for a reason, and when they’re gone, give the shirt to Goodwill.

  8. Dave says

    July 12, 2012 at 11:25 AM

    Nice Seinfeld reference Beth! Just went up a notch in my book.

  9. Ha says

    July 12, 2012 at 12:40 PM

    Only two types of men where HI shirts – 1. party animals 2. homosexuals

  10. Thomas R. says

    July 12, 2012 at 1:08 PM

    I think there are some good looking ‘modern’ Hawaiian print shirts out there. I have a nice white with subtle gray florally print on it from the gap. I even wore it to a luau in Hawaii a few weeks ago. I would never wear or recommend wearing anything that looks like its made from recycled board shorts from the 90s or if it has any type of tropical bird on it.

  11. John says

    July 12, 2012 at 1:13 PM

    Most online sellers of Aloha shirts will list the garment measurements, so one can get a size that works for them. In most cases, I’ve found that sizing down works well. The shirt is still loose, but not baggy. Also, rayon has a unique property in that it doesn’t retain body heat like other synthetics (rayon is technically made from cellulose, a natural, plant-derived fiber). On the mainland, in the summer, with chinos and drivers, Aloha shirts can be Friday casual, which incidentally started with Aloha Fridays in Hawaii. Mahalo and aloha!

  12. Jeff says

    July 12, 2012 at 5:44 PM

    President Truman says sure, wear the shirt.
    http://www.theatlantic.com/politics/archive/2011/11/picture-of-the-day-truman-appears-on-1951-life-cover-in-hawaiian-shirt/248832/

  13. LW says

    July 13, 2012 at 5:58 AM

    Drew is pretty much right on here. I’ve lived on Maui for over a decade now and that’s about the size of it out here. Most settings here are a solid step or three more casual then they would be in most places on the mainland, so a nice “Hawaiian shirt” (referred to as ‘aloha shirts’ or an aloha print out here) and pressed pants are often accepted as dressed up. The lines aren’t as defined on Maui. I could be at a wedding wearing a suit and tie talking to another guest in an aloha shirt and pressed pants, and neither of us would necessarily be considered over or under-dressed. It’s more or less about feeling good and being comfortable whatever you decide to wear. Obviously different rules on the mainland.

    That said, I don’t wear them. I don’t even own one.

  14. LW says

    July 13, 2012 at 5:59 AM

    P.S.
    If you ever do wear one. Never, ever, tuck it in. Even if you drive a 308.

  15. Samaritan says

    July 13, 2012 at 6:51 AM

    That’s Brad Pitt though.

  16. Raymond says

    July 13, 2012 at 10:45 AM

    The best Hawaiian shirts are either actual vintage or those trying to look it. I mean the kind of thing that a soldier would wear at a bbq after VJ Day.

  17. Alex says

    July 13, 2012 at 8:16 PM

    Hawaiian shirts can be decent attire (i wear one at least once a week) but they are only ok if they are made from the right fabric and they must not be above a size medium before you start to look “kitschy”. You must buy it in classic 1950’s style; you can not go for a 1980’s tourist look here without looking like an idiot. If you get it in the right cut, tuck it in with pants, DO NOT WEAR WITH SHORTS. They also look great as a shirt to wear with a bathing suit at the beach or pool. I also have a thing about rolling the sleeves up… People always comment on how they love the fact that I have the guts to wear a Hawaiian shirt (and look good in it too) Land’s end has a great one to get you started
    http://www.landsend.com/pp/mens-short-sleeve-hoffman-fabrics-printed-shirt~237641_-1.html?bcc=y&action=order_more&sku_0=::J18&CM_MERCH=IDX_men-_-new-arrivals&origin=index

  18. John says

    July 14, 2012 at 7:45 PM

    As a man I say yes. I don’t like my Hawaiian shirts to have a design that’s too “crowded”, but just the right amount of palm trees and the right fit, it’s awesome, especially on a sail boat.

  19. Paul says

    July 18, 2012 at 9:16 PM

    http://www.google.com/imgres?q=max+payne+hawaiian+shirt&um=1&hl=en&sa=N&biw=1366&bih=643&tbm=isch&tbnid=uTIv4GotCP31AM:&imgrefurl=http://www.pcgamer.com/2012/02/24/max-payne-3-pc-screenshots-have-even-hotter-hawaiian-shirt/&docid=ky1RxWHcYCLCFM&imgurl=http://media.pcgamer.com/files/2012/02/Max-Payne-3-PC-2.jpg&w=1920&h=1058&ei=mXsHUOakLMnYqgGMndHoBA&zoom=1&iact=hc&vpx=357&vpy=107&dur=721&hovh=167&hovw=303&tx=139&ty=115&sig=112974262172165238900&page=1&tbnh=101&tbnw=184&start=0&ndsp=18&ved=1t:429,r:1,s:0,i:78

  20. Derek says

    July 19, 2012 at 3:11 PM

    Am I the only one who thought “oil change girl sounds sexy, other ripped jeans girl sounds trendy and uncool”?

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