Oversized Dress Shirt

Isla Brooks
19 min readMar 14, 2024

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Looking for a dress shirt that stands out from the crowd? Look no further than our roundup of oversized dress shirts. These stylish and comfortable shirts are designed to make a statement while still providing a perfect fit. From classic cuts to bold patterns, our selection of oversized dress shirts will have you looking sharp and feeling confident. Read on to discover our top picks.

The Top 15 Best Oversized Dress Shirt

  1. Elegant White Striped Oversized Button-Up Shirt — Classic Oversized Stripe Shirt — Weekend Style with 65% Cotton, Effortless Wear
  2. Topman Extra Large Grid Plaid Shirt with Multiple Sizes — Experience the ultimate weekend style with the Topman Long Sleeve Super Oversized Fit Grid Plaid Shirt in Multi, featuring a large chest patch pocket, button cuffs, and a classic check pattern.
  3. Oversized Lightweight Dress Shirt in Grey — Experience the perfect blend of style and comfort with the Topman Oversize Button-Up Shirt Grey, crafted from lightweight cotton and featuring neat pleats for a classic yet oversized silhouette.
  4. ASOS Oversized Button-Up Revere Shirt in White Multi — Embrace effortless style with this ASOS Design Oversize Button-Up Revere Shirt in White Multi, featuring an exclusive cotton-linen blend and a playful 70s vibe.
  5. Tall Men’s Stylish Ombre Check Oversized Dress Shirt — Tall men, rejoice! This Ombre Check Overshirt is the perfect fit for your 6ft 4 and over frame, providing tailored style and versatility for any occasion.
  6. Stylish Dropped Shoulder Oversized Dress Shirt for Summer — Unleash your style with the trendy women’s oversize button collared shirt in dusty pink, perfect for summertime events and vacations.
  7. Oversized Textured Panel Button-Up Shirt in Black — Elevate your wardrobe with the stylish and versatile Topshop Oversize Textured Panel Button-Up Shirt in Black, featuring long sleeves, button cuffs, and a polished front panel accent.
  8. Oversized Pleated Short Sleeve Dress Shirt in Beige — An oversized pleated short sleeve shirt in beige, perfect for adding a subtle sophistication to any outfit.
  9. Koton White Oversized Button Up Dress Shirt for Women — Elevate your wardrobe with this versatile, oversized cotton poplin dress shirt, offering a timeless, relaxed fit and perfect for a range of outfits.
  10. Oversized Stripe Button-Up Oxford Shirt — Transform your wardrobe with the ASOS Design Stripe Oversize Button-Up Oxford Shirt in White, featuring a spread collar, long sleeves, and a stylish chest patch pocket. Perfect for layering or wearing solo, this exclusive shirt is available at ASOS.
  11. Oversized Button-Up Shirt in Camel by Topshop — Stand out in style with Topshop’s sophisticated camel-hued Oversize Button-Up Shirt, offering a distinctly modern twist on the classic dress shirt.
  12. ASOS Design Oversized Button-Up Oxford Shirt in White — Embrace a sophisticated, versatile look with the ASOS Design Oversized Button-Up Oxford Shirt in White, featuring a classic white hue and comfortable long sleeves.
  13. Oversized Dress Shirt — Preppy and Casual — Embrace effortless style with the Madewell Signature Poplin Oversized Button Front Shirt in Black, a versatile addition to any wardrobe that combines comfort and preppy flair.
  14. Elevated Oversized Plissé Dress Shirt for a Streetwear Spin — Transform your casual wardrobe with this ASOS Oversized Plissé Button-Up Shirt in Cream, adding a touch of edgy sophistication to your everyday look.
  15. Oversized Check Dress Shirt — Mid Blue — Experience comfortable style with Topshop’s Mid Blue Oversize Check Textured Cotton Button-Up Shirt, a perfect fit for layering and featuring two-button cuffs.

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Reviews

🔗Elegant White Striped Oversized Button-Up Shirt

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Slipping into this Topman Oversize Stripe Button-Up Shirt feels like putting on a soft, breathable summer dream. The roomy fit is perfect for those lazy weekends when you just want to lounged in style.

The mixed stripe pattern adds a fun twist to the classic button-up, making it stand out from the crowd. The spread collar and long sleeves with button cuffs give it a touch of sophistication, while the 65% cotton and 35% polyester blend ensures comfort and durability.

The shirt is machine washable, making it hassle-free to clean and line dry, so you can always look your best. Overall, this shirt effortlessly combines comfort, style, and practicality into one amazing package — a true must-have in your wardrobe.

🔗Topman Extra Large Grid Plaid Shirt with Multiple Sizes

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I recently came across Topman’s Long Sleeve Super Oversized Fit Grid Plaid Shirt in Multi. The first thing that caught my eye was its oversized fit, which added a unique touch to this classic button-up shirt. The shirt is covered in a check pattern and has a large chest patch pocket that makes it stand out from other weekend-ready styles.

One of the best features of this shirt, in my opinion, is the spread collar. It’s not too wide, but just enough to give a relaxed feel to the shirt, perfect for a casual weekend look. The long sleeves with button cuffs are another highlight, providing extra coverage without sacrificing style.

However, there were a couple of things that could have been improved. First, the material is a blend of 65% polyester and 35% cotton. While this makes the shirt easy to care for, it also doesn’t breathe as well as some other materials. I also had to be careful when washing and drying, as the instructions specified that it should be machine-washed and line-dried.

Overall, the Topman Long Sleeve Super Oversized Fit Grid Plaid Shirt in Multi is a stylish addition to any weekend wardrobe. Its unique oversized fit adds a touch of flair to a classic button-up look, but its material could use some improvement for better breathability.

🔗Oversized Lightweight Dress Shirt in Grey

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I recently added a Topman Oversized Button-Up Shirt in Grey to my wardrobe and I must say, it’s been a game-changer. The lightweight cotton material feels so comfy, making it perfect for those warm summer days.

What stands out the most is the neat pleats at the back and sleeves, which give the oversized fit a classy touch. While some may see the oversized fit as a downside, I personally love how it adds a casual, effortless feel to my outfits.

Overall, I’m very happy with this purchase and would definitely recommend it for anyone looking for a versatile, stylish button-up shirt.

🔗ASOS Oversized Button-Up Revere Shirt in White Multi

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Imagine wearing a shirt that turns heads and makes a statement. The ASOS Design Oversize Button-Up Revere Shirt in White Multi offers just that. Crafted from a comfy breathable blend of cotton and linen, this shirt boasts eye-catching throwback graphics that give it a unique charm.

While the 70% cotton and 30% linen blend may seem appealing, the fabric can be a bit of a hit-or-miss, depending on the person’s preference. One downside is the notched collar that might feel a bit snug, but it adds a fun twist to the overall design.

The length of this shirt is quite a sight to behold — it’s a whopping 27 1/2 inches long. If you’re on the taller side, you might think it’s a perfect fit. But if you’re closer to average height, size down to avoid looking like a giant compared to others.

Unfortunately, this shirt struggles to maintain its quality over time. In my experience, the shirt looked a bit cheapy up close, which was a letdown.

Despite the pros and cons, the ASOS Design Oversize Button-Up Revere Shirt in White Multi still has a certain allure. It’s a daring piece to wear, and with some minor adjustments, it can be a quirky addition to anybody’s wardrobe.

🔗Tall Men’s Stylish Ombre Check Oversized Dress Shirt

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Oh, this oversized button-up shirt with an ombre check overshirt in black — yes, it stands out. Designed for the taller fellas, it fits like a dream. Perfect for the office, weddings, and even casual outings, it’s a closet essential.

The tailoring is spot on and flattering, no matter the occasion. A piece you’ll surely cherish.

🔗Stylish Dropped Shoulder Oversized Dress Shirt for Summer

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Last week, I decided to try out this Oversize Button Collared Shirt in a Dusty Pink color. I’ve always been a fan of oversized shirts, and the combination of its unique style with the dusty pink color caught my eye.

The first thing I noticed when I put it on was how comfortable it was. The lightweight fabric made it perfect for a casual summer day, and the dropped shoulder and pleat details on the sleeves really made a statement.

However, one thing that I didn’t expect was that the shirt wasn’t as oversized as the description suggested. Although the cut was loose enough to be comfortable, it didn’t fully live up to its “oversized” tag.

Despite this small disappointment, overall, the shirt was a stylish addition to my wardrobe and a refreshing change from my usual t-shirts.

🔗Oversized Textured Panel Button-Up Shirt in Black

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I recently stumbled upon the Oversize Textured Panel Button-Up Shirt from Topshop’s collection, and I must say, it exceeded my expectations! The overall cut is indeed oversized, which adds a certain charm to the shirt. Now, let me tell you about the front panel accent. It really brings the shirt’s details to life and adds an element of sophistication.

Unfortunately, the collar is a bit wide for my taste, but it might be perfect for those who prefer it spread. As for the sleeves, they’re long enough to keep them under the coat, but not too long that they become inconvenient when reaching for anything.

In terms of materials, I appreciate the blend of 57% polyester, 42% polyester, and 1% elastane. It’s a comfortable material to wear, and it’s machine washable — which is a true lifesaver when you’re dealing with a large shirt that usually requires special care.

And the cherry on top? It’s imported! So, you know you’re getting a one-of-a-kind piece. Overall, this shirt is a perfect blend of timeless style and modern flair, but there are some minor aspects that could be improved.

🔗Oversized Pleated Short Sleeve Dress Shirt in Beige

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I recently stumbled upon the boohooMAN Pleated Short Sleeve Oversized Boxy Shirt in beige, and let me tell you, it’s been a game-changer for my everyday look. This shirt is the perfect blend of casual and dapper, making it a versatile addition to any wardrobe.

The pleated details add a subtle touch of sophistication, while the oversized fit provides a comfortable and relaxed feel. Pairing this shirt with a blazer and skinny jeans can create a polished look for professional settings, and switching it up with Chelsea boots can effortlessly transition to a night out.

One of the best aspects of this shirt is its color — beige provides a soft neutral base that can easily be paired with various colors and styles. It’s a great option for those who want to mix and match outfits without worrying about clashing colors.

However, there’s always room for improvement. One downside is that this shirt is not the most breathable, which can be a slight inconvenience during warmer months. But overall, the boohooMAN Pleated Short Sleeve Oversized Boxy Shirt is a great investment for anyone looking to elevate their everyday style with subtle yet impactful elements.

🔗Koton White Oversized Button Up Dress Shirt for Women

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I had the pleasure of trying out the Koton Women’s Shirt in White last week and it truly lives up to expectations. The relaxed and loose fit, with its dropped shoulder, makes it a perfect summer wardrobe addition. The cotton poplin fabric is not only comfortable but also adds a touch of elegance to my outfits.

One of the features that stood out to me was the large pointed collar, which gives this shirt a classic and minimalistic touch. The shirt’s straight hemline is effortlessly paired with both my straight-leg jeans and tailored pencil skirts. Machine washing it in cold water was a breeze, and retaining its shape and color has been impressive so far.

However, I did notice the sizing to be slightly off, as the shirt ended up a bit larger than expected. The wearer in the provided image is a 177cm model, which is taller than most, but I think the sizing could have been accommodated better for a more consistent fit.

Overall, the Koton Women’s Shirt in White is a great option for those seeking a versatile and stylish wardrobe piece. Just keep the sizing in mind and adjust the dress accordingly for a perfect fit.

🔗Oversized Stripe Button-Up Oxford Shirt

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Recently, I added a touch of class to my wardrobe with the ASOS Design Stripe Oversize Button-Up Oxford Shirt in White. The elegant pinstripes made it stand out, adding a unique element to traditional office wear. Layering it up or rocking it solo was easy with the spread collar and long sleeves, and the two-button cuffs gave it a refined look.

However, I noticed that the shirt was a bit too large, which could make it challenging to find the perfect fit. Despite this small issue, this shirt is an excellent choice for anyone seeking a stylish and comfortable addition to their wardrobe.

🔗Oversized Button-Up Shirt in Camel by Topshop

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I’ve had the pleasure of wearing this Oversize Button-Up Shirt in Camel from Topshop, and it has quickly become one of my favorite staple pieces. The first thing that caught my eye was the dramatically oversized fit; it adds a modern touch to classic button-up shirts, making it both unique and stylish. The spread collar and long sleeves with button cuffs give a polished look, perfect for dressing up or dressed down occasions.

However, the material composition, a mix of 90% polyester, 6% viscose, and 4% wool, can be somewhat stiff, which might not be ideal for those seeking a softer feel. But on the upside, the shirt is machine washable and can be line dried, adding convenience to the overall experience. Lastly, being made in the USA or imported adds some level of confidence to its quality. In summary, this Oversize Button-Up Shirt in Camel from Topshop is a standout piece in my wardrobe, but the slightly rigid fabric is something to consider before purchasing.

🔗ASOS Design Oversized Button-Up Oxford Shirt in White

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Last month, I added the oh-so-versatile ASOS Design Oversize Button-Up Oxford Shirt in White to my wardrobe. This classic shirt with its timeless white hue has been a great addition as it can be layered up or worn solo, fitting effortlessly into my current style. With that said, the shirt falls considerably longer than I anticipated, but it did cover my tummy.

The fabric’s slightly thick texture, suitable for the chilly winter nights, offers just the right amount of warmth during California’s slightly cooler evenings. The button-up design, combined with its spread collar and long sleeves, gave me the impression of an extra effort to achieve that vintage look. However, the shirt turned out to be just a tad too tight around my arms, shoulders, and pit area, making me uncomfortable.

Overall, this button-up oxford shirt has its good and bad points. While it ticks the right style boxes, its sizing issue leaves much to be desired.

If ASOS could address this sizing quirk, I swear it’d be a standout in the season of layering up! .

🔗Oversized Dress Shirt — Preppy and Casual

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Recently, I came across the Madewell Signature Poplin Oversized Button Front Shirt in black. I was intrigued by the combination of a classic design with an oversized fit. I figured it might be the ideal wardrobe essential for a versatile appearance.

It arrived neatly packed with a note expressing the company’s dedication to maintaining their products in pristine condition. I eagerly unpacked it, ready to try it on. The moment I slid it on, I felt a sense of comfort and relaxation. The oversized fit was just right, not too loose or toobaggy. Its relaxed vibe and lightweight quality made it perfect for casual occasions or even lounging at home.

One of the features I loved most was the buttoned-up look it offered. You can easily layer it with jeans for a casual appearance or opt for a more professional look by tucking in the shirt. The patch chest pocket added a touch of sophistication to the piece, and the drop shoulders were a great bonus. The shirt also fit well, leaving enough room for a natural and comfortable movement.

What truly stood out was how soft the fabric was, making it ideal for a relaxing weekend. Plus, it never seemed to crease, which was a pleasant surprise. I did find the length a bit short compared to the descriptions, but it wasn’t too much of a concern.

However, nothing is perfect, and there were a couple of areas in the design that could use improvement. The most noticeable was the exposed seams on the pockets, which gave the shirt an unpolished appearance. Additionally, the underside of the shirt could be longer for a better tuck-in look.

Despite these minor imperfections, the Madewell Signature Poplin Oversized Button Front Shirt in black served its purpose as an elegant wardrobe staple. I’d definitely recommend this to anyone seeking to bring a touch of preppy charm to their style.

🔗Elevated Oversized Plissé Dress Shirt for a Streetwear Spin

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Recently, I tried on ASOS Design’s Oversize Plissé Button-Up Shirt in Cream, and I have to say, it brought a touch of streetwear edginess to my wardrobe. The plissé fabric added a delightful textural intrigue, and the oversized silhouette provided versatility in styling. However, I did face a few challenges with this shirt.

First, the shirt’s size seemed massive on me, though it worked well as an oversized piece. Second, the stitching around the shoulder was a bit faulty, which was disappointing considering the otherwise quality construction.

Lastly, some reviews highlighted issues with the sizing, so make sure to choose your suitable size carefully. Overall, this shirt is a great option for those looking for an edgy oversized look but be prepared for possible sizing adjustments as mentioned by previous buyers.

🔗Oversized Check Dress Shirt — Mid Blue

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I’ve been wearing this Mid Blue oversize check button-up from Topshop in my daily life, and it’s been a game-changer for my wardrobe. The textured cotton fabric has a unique feel, making it stand out from other shirts I own. The oversized fit is perfect for those days when I want a roomier look, and the long sleeves with two-button cuffs are a nice touch.

While I love the style and feel of the shirt, I’ve noticed that it can be a bit difficult to find the perfect fit, especially considering its oversized nature. Moreover, the shirt requires a bit of care in washing, as it needs to be line dried instead of thrown in the machine, which can be inconvenient for some.

Overall, the Topshop Mid Blue oversize check button-up shirt is a stylish and unique addition to any wardrobe, but it might not be the best choice for those who prefer a more standardized fit or for those who want an easier care routine for their clothing.

Buyer’s Guide

When it comes to dressing up for a special occasion, comfort and style are just as important as fitting in with current fashion trends. Oversized dress shirts are gaining popularity, providing users with a stylish and comfortable option for both formal and semi-formal events. Whether you’re looking for a unique statement piece or a classic design, it’s essential to understand the important features, considerations, and advice for choosing the best oversized dress shirt.

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Important Features

  1. Sizing: The most critical factor to consider when purchasing an oversized dress shirt is the sizing. Since these shirts are purposefully larger than your typical slim-fit shirt, be sure to check the size chart and find your perfect fit. It’s essential to keep in mind that an oversized shirt can also provide a looser, more comfortable fit, so don’t be afraid to size up if that’s your preference.

Fabric and Material

  1. Fabric: Oversized dress shirts are available in a variety of materials and fabrics. Consider the event and your comfort level when selecting the fabric for your shirt. Some common materials used include cotton, silk, and polyester blends. Cotton is a comfortable and breathable option, especially for summer events, while silk provides a luxurious look and feel. Polyester blends can be great for a blend of style and durability.
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Care and Laundering

  1. Care Instructions: To maintain the quality and longevity of your oversized dress shirt, it’s essential to follow the care instructions provided by the manufacturer. Delicate materials, such as silk, may require special cleaning methods. Wash and dry your shirt according to the instructions, and store it in a cool and dry place when not in use.

Considerations

  1. Occasion: The type of event you’ll be wearing the oversized dress shirt to will play a significant role in your choice. If you’re attending a black-tie event, opt for a classic, elegant design. However, a semi-formal occasion might call for a more casual, relaxed fit. Consider the dress code and theme of the event to find the perfect balance between style and comfort.
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FAQ

What is an oversized dress shirt?

An oversized dress shirt is a garment designed to have a larger fit than traditional dress shirts. This style has gained popularity in recent years as it offers a modern and relaxed look while still maintaining a formal appearance. Oversized dress shirts typically feature a larger collar, looser sleeves, and a fuller fit throughout the body.

The oversized design allows for easier movement and comfort, making it an excellent choice for those who prefer a more relaxed fit in their dress shirts. Despite the loose fit, oversized dress shirts still work well with tailored suits and formal occasions, giving the wearer a unique and stylish look.

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What are the benefits of wearing an oversized dress shirt?

Oversized dress shirts offer several benefits compared to traditional dress shirts. Primarily, they provide increased comfort and ease of movement due to their looser fit. This can be especially appealing for individuals who spend long hours at work or in formal settings where they may need to move around frequently.

Additionally, oversized dress shirts can help balance out the formality of an outfit. Pairing a more casual, oversized dress shirt with a well-tailored suit can create a unique and stylish look that stands out from the crowd. The relaxed fit can also make the wearer feel more confident and comfortable in formal settings.

How do I choose the right size for an oversized dress shirt?

Choosing the right size for an oversized dress shirt is essential to ensure a proper fit. To find the best size, start by measuring your chest, waist, and hips. These measurements will help you determine the ideal size range for your oversized dress shirt. It’s essential to note that oversized dress shirts typically have a larger fit than traditional dress shirts, so you may need to go up a size or two from your usual measurements.

When trying on oversized dress shirts, ensure that the collar is comfortable and sits at the right height on your neck. The sleeves should be long enough to cover your shirt cuffs but not too tight, allowing for easy movement. Lastly, the body of the shirt should be loose but not so baggy that it compromises the overall look and fit.

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What materials is the oversized dress shirt typically made from?

Oversized dress shirts are typically made from high-quality materials that offer both comfort and durability. Popular materials for dress shirts include cotton, silk, and linen. These materials are breathable, making them ideal for warmer weather and formal events. They also have a natural drape, which helps create a relaxed and comfortable fit.

Cotton is a versatile and popular choice for dress shirts, as it’s durable, easy to care for, and comes in a variety of weaves and finishes. Silk and linen are more luxurious options, offering a smooth and lightweight feel that is perfect for hot weather and formal events. These materials can be more expensive but are known for their exceptional comfort and breathability.

Are oversized dress shirts appropriate for formal occasions?

Yes, oversized dress shirts can be appropriate for formal occasions when styled correctly. The key is to maintain a balance between the relaxed fit and the overall formality of the event. A well-tailored suit paired with an oversized dress shirt can create a unique and stylish look that is suitable for formal events. However, it’s essential to ensure that the oversized dress shirt does not compromise the formality of the outfit and that the fit is still flattering and comfortable.

Additionally, consider the dress code of the event. If the event is more casual, an oversized dress shirt may be more appropriate. However, if the event is more formal or traditional, it may be best to opt for a more traditional dress shirt with a fitted or semi-fitted design to maintain the appropriate level of formality.

How do I care for my oversized dress shirt?

Proper care is essential to maintain the quality and longevity of your oversized dress shirt. Start by reading the care label, as different materials require different cleaning methods. Generally, cotton and linen dress shirts can be machine washed on a gentle cycle, while silk shirts should be hand-washed or taken to a professional cleaner.

When drying your oversized dress shirt, avoid high heat, as this can damage the fibers and cause shrinkage. Instead, air-dry your shirt by hanging it on a clothesline or drying rack. If you must use a dryer, use the lowest heat setting and remove the shirt from the dryer while it’s still slightly damp to prevent any shrinkage or wrinkles.

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