I am here to be the one to officially tell you that it is okay to tuck in your shirt. I know, I know, this can be a tricky feat especially if you still associate tucking in your shirt with either looking like a truck driver or like you are in the fifth grade; definitely discard both theories. Tucking in your shirt can completely transform an outfit, and it can also allow you to take shirts that would normally be too big or bulky and make them look great.
First, when wearing high-waisted anything, please, please, please tuck in your shirt! The only way to wear such looks is with a tucked-in shirt; whether you prefer tight or loose tops, it doesn’t matter. High-waisted jeans must be paired with a shirt tucked in, and high-waisted dress pants look best and more polished with a tucked-in shirt.  Everyone, embrace the tuck-in!
Next, I know the idea of tucking a shirt into a natural waist or low-rise pant is a scary concept  (For me, it brings back some scary flashbacks of wearing Nike t-shirts and flared jeans in sixth grade). But, tucking shirts into these pant styles is now okay. Tucking a baggy shirt into some jeans is absolutely acceptable, and even–gasp!–stylish!
The key to wearing this look best is keeping everything else loose. As a first-time tucker-inner, I attempted a plaid button-up shirt with jean shorts and it worked perfectly. So, I suggest you go with something similarly simple and going from there. A definite “do”? Pairing this look with a belt.
Tucked in shirt

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