Untucked dress shirts look best when they’re shorter in length overall. Lift up your arms to see how long or short your garment is. If your shirt lifts up to the point where you can see your midsection, then you shouldn’t wear it untucked.
Shirts with curved hemlines and shirt tails are designed to be tucked into dress pants, and are typically worn with jackets or blazers, or as part of a suit ensemble. Shirts with straight hems can be squared-off or curved along the bottom.
Shirts with tight, stiff collars are more designed to be paired with ties, dress pants, suits, and other formal attire.
To ensure that your clothing fits comfortably, take some basic measurements and compare them to a sizing chart. This can help give you a better idea of what size shirt is best for your body type.
Always err on the side of caution when planning an outfit. If you aren’t sure if the occasion is formal or casual, leave your dress shirt tucked in. For instance, you’ll probably want to tuck in your shirt when attending a wedding, unless the event is explicitly described as a relaxed, casual.
If you’re planning an outfit for warmer weather, choose a short-sleeved dress shirt or polo shirt instead.
For instance, try pairing a blue-patterned dress shirt with dark blue jeans. Create a relaxed look by rolling up the sleeves, or add a formal touch by sliding on a watch. Belts are an acceptable accessory to wear with an untucked shirt. [8] X Research source
Leaving the top button tied will make your outfit stiff and uncomfortable.
For example, try pairing a short-sleeved, untucked dress shirt with a pair of jeans and some comfortable tennis shoes.
Belts, watches, and aviators are great accessories to try with this type of outfit. For example, try pairing a blue short-sleeved dress shirt with a pair of green chinos, along with professional, neutral-toned desert boots.
While some people prefer to tuck in dress shirts beneath a sweater, there’s nothing wrong with the bottom of the shirt being visible beneath the garment. For example, try slipping on a dark green sweater over a white dress shirt. Pair these items with a pair of jeans, along with a comfortable pair of loafers. For instance, a pair of loafers can go well with a pair of dark jeans.
If you’re trying to stay warm, opt for a casual jacket or coat instead.
Since an untucked shirt is only used for relaxed, casual occasions, you don’t need to slip on fancy dress shoes or wingtips.
