A clean or ever-so-slightly cropped pair with a dark finish and slick, minimal-leaning boots (like, say, these) will never not look cool.
The colored items on the sailors chest are their military awards commonly known as ribbons. Some ribbons will have a corresponding medal worn with full dress uniforms
Offered here as: Paper Pattern and the Original pattern
Summer maxi dresses with short sleeves, bare shoulders, or thin straps, winter maxi dresses with long and flared sleeves...the maxi dress will entice you
Neutral flat sandals keep the look grounded and brunch-appropriate, especially when you expect to walk afterward
Just ensure if you're wearing the shirt untucked, it should fall no longer than the middle of your back pockets to maintain a polished look