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One of the most common questions we get is whether you should wear your shirt tucked or untucked. Don't stress. Here are some simple rules of thumb to follow to hope you decide how to wear your shirt.
Rule of Thumb #1 - Bottom Design Shirt
If you are wearing bottom design shirt, which is a shirt where the design spans across the front of the shirt in an uninterrupted image all the way down to the bottom of the shirt, we recommend wearing such a shirt untucked. The reason for this is that the shirt design is like a piece of artwork or a painting. It is meant to be enjoyed and appreciated as a whole. By tucking in the shirt, you are covering the bottom of the shirt which prevents it from being seen. This would be the equivalent to putting nice painting on display but covering the bottom up with paper or hiding it behind some furniture. If the design doesn't go all the way to the bottom of the shirt and can be tucked in without covering up part of the design, then it's probably okay to tuck it in. But as a general rule, don't tuck in a bottom design shirt.
Part of a bottom design shirt hidden when tucked in
Border print shirt without design elements at the bottom looks okay tucked or untucked
Rule of Thumb #2 - The Casual Look
Hawaiian shirts are casual by nature so when we say "casual look", we really mean casual for a Hawaiian shirt. If you are going to some sort of casual fun event like a backyard BBQ, pool party or day a the beach we generally recommend wearing the shirt untucked. You can wear it with jeans or shorts and achieve an effortlessly relaxed and ready-to-party look.
Wearing a Magnum PI shirt untucked at a beach house party
Rule of Thumb #3 - The Dressed Up Aloha Look
If you are going for a look that is a little more cleaned up and tidy (and you aren't wearing a bottom design shirt), we recommend tucking the shirt in. In Hawaii, it is very common for office workers to wear a toned down Hawaiian shirt tucked into dress slacks or khakis to work. Tucking the shirt in looks more professional in this environment. Younger workers or perhaps those in less conservative industries might be able to wear their shirt untucked if the shirt is more fitted. But under most circumstances when you want to maintain a professional or clean image in a Hawaiian shirt, it's probably better to tuck your shirt in.
Tucking a shirt in for a professional office look
Rule of Thumb #4 - Go With the Flow
One of the great things about fashion is that there is not right or wrong. Sometimes going against fashion convention is precisely the point. If you have a sense of personal style, just go with it and express yourself however you want.
The Eyeball Test
The bottom line is that ultimately you want to achieve a look that you're happy with. When all else fails, we always resort to the Eyeball Test. Put your shirt on and tuck it in or leave it untucked into whatever pants you're wearing. If it looks good to you, you're good to go. If somehow it looks weird to you, then change it. If you need second opinion, ask someone. If it looks good despite breaking one of the rules above, don't worry about it. Just wear it and have fun!