How to Wear a Dress Shirt Untucked

Although untucked shirts aren’t a great option for formal events, they can add a layer of polish and style to a casual ensemble. Before selecting a dress shirt to wear, compare the garment against a few basic guidelines to see if it can be untucked. Then, you can experiment with different sweaters, jeans, and various kinds of shoes until you find a casual or formal outfit that works well for you!

Method 1

Method 1 of 3:

Choosing the Right Dress Shirt

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1
Select a shirt that only goes down to your zipper. Try on your dress shirt in front of a mirror, so you can see how long the shirt tails are. While you don’t have to measure the garment, see if the hem drifts below the middle of your pant’s zipper. If the shirt is long and baggy, set it aside and try on a different garment. Additionally, check that the shirt doesn’t ride up on your midsection.^{[1]XResearch source}
- 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.
2
Untuck shirts that have a straight hemline. Examine the bottom section of your shirt to see if it’s straight or curved. While many dress shirts can be worn tucked or untucked, note that shirts with curved, uneven seams with obvious shirt tails are designed to be tucked into your pants.^{[2]XResearch source}
- 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.
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3
Opt for dress shirts with loose collars to create a casual outfit. Pinch the fabric of your collar to see how stiff or loose the material is. If the collar is stuffed or made with an especially sturdy fabric, set the shirt aside for a more formal occasion. If the collar is loose, then you can repurpose the shirt for a business-casual or everyday look.^{[3]XResearch source}
- Shirts with tight, stiff collars are more designed to be paired with ties, dress pants, suits, and other formal attire.
4
Pick out dress shirts that comfortably fit so you can look professional. Try on different garments to see if they fit over your back, shoulders, and midsection without being too tight or baggy. If the shirt is too loose, you might look unpolished. However, if you choose a garment that’s too tight, your outfit might come off as awkward and uncomfortable. If the dress shirt doesn’t fit properly, don’t wear it untucked.^{[4]XResearch source}
- 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.
5
Gauge the formality of the event before attending in an untucked shirt. Think about the purpose of your outing and determine if it’s a fancy or casual event. If the event is considered black-tie, be sure to tuck in your dress shirt. If you’re going out for drinks or to a casual party, then you’ll be fine going out with an untucked shirt.^{[5]XResearch source}
- 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.

Method 2

Method 2 of 3:

Creating a Casual Outfit

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1
Roll up your sleeves for a more casual, on-the-go look. If you’re leaving your shirt untucked, there’s no reason to leave your arms constricted by long shirt sleeves! Take the cuff of your shirt sleeve and roll it backwards until you reach your elbow. Try to roll your sleeves evenly on both sides, so your outfit still looks polished and professional.^{[6]XResearch source}
- If you’re planning an outfit for warmer weather, choose a short-sleeved dress shirt or polo shirt instead.
2
Pair an untucked dress shirt with jeans to give off a casual vibe. Choose a comfortable pair of jeans in your preferred style. As you put the outfit together, check that the dress shirt doesn’t fall below the middle of the zipper. You can finish off the outfit with a formal or casual pair of shoes, depending on your own personal preference.^{[7]XResearch source}
- 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.
3
Keep the top 2 buttons undone to give yourself some breathing room. If you’re not wearing a tie or similar accessory, you don’t need to keep all of your dress shirt’s buttons secured into place. Instead, leave the top buttons open, while the rest are still secured into place. If you’d prefer to create a more polished look, only leave the top collar button undone.^{[8]XResearch source}
- Leaving the top button tied will make your outfit stiff and uncomfortable.
4
Pick sneakers or athletic shoes to create a more casual look. If you’re planning to be on-the-go, opt for a pair of shoes that fit comfortably and provide you with a lot of mobility. If you don’t like wearing sneakers or trainers, opt for tennis shoes or another type of comfortable footwear.
- For example, try pairing a short-sleeved, untucked dress shirt with a pair of jeans and some comfortable tennis shoes.

Method 3

Method 3 of 3:

Building a Dressier Ensemble

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1
Wear a dress shirt with nice pants or chinos to a formal setting. Instead of choosing a pair of baggy pants, opt for a pair of chinos or dress pants that have a sleek, professional look. Choose soft, muted colors that work well in an office or other professional atmosphere, like dark green or tan. For an especially comfortable and stylish ensemble, choose an untucked, short-sleeve dress shirt to complete your outfit.
- 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.
2
Slip on a sweater to create a stylish ensemble. Add an extra layer of warmth to your outfit during the colder months by slipping a sweater overtop of an untucked dress shirt. Be sure to select a dress shirt that fits correctly and doesn’t fall over the midsection of your pants zipper.^{[9]XResearch source}
- 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.
3
Avoid wearing jackets or blazers with an untucked shirt. While untucked shirts are a comfortable option for social gatherings and casual, everyday outfits, don’t try to mix them into your especially formal attire. If you’re choosing to wear a suit or blazer of any kind, keep your shirt tucked into the waistline of your pants.^{[10]XResearch source}
- If you’re trying to stay warm, opt for a casual jacket or coat instead.
Tip: Follow your gut when planning an outfit with a blazer. If the blazer is just a casual accessory, then you might be able to pair it with an untucked dress shirt.
4
Choose loafers if you’re headed to a fancier location. When adding the finishing touches to your outfit, look for a pair of shoes that add a layer of polish to your outfit without appearing over-the-top. If you’re headed to a party or other social gathering, slip on a pair of loafers to compliment the relaxed style of your untucked dress shirt.^{[11]XResearch source}
- Since an untucked shirt is only used for relaxed, casual occasions, you don’t need to slip on fancy dress shoes or wingtips.