Here’s a no-nonsense guide on finding dress shirts for the larger man.
Finding clothes for bigger guys is not easy. These days, if you’re bigger than an XL — which is often more like a true large — shopping becomes a headache.
To make matters worse, it’s even harder to find high-quality clothing that fits. Sure, you can grab a shirt that fits off Amazon, but you’ll be lucky if it lasts a few months.
That’s also true for most shirts sold at big and tall retailers like DXL or big box stores like Men’s Wearhouse. (And the clothing that does last just doesn’t feel good.)
All of this creates a real problem for big guys who need to buy dress shirts. Dress shirts are still typical daily wear for many jobs, but premium options are hard to find in anything above a 2XL.
Most guides tell you to get shirts tailored, and there’s some truth to that. But where do you even start, and which brands can you rely on? We’re going to answer those questions and more in this guide.
The Dress Shirt Defined
Before we dive into the finer points of the dress shirt, let’s establish what a dress shirt actually is.
Plenty of guys assume that a dress shirt is just a fancier button-up shirt. That’s kind of true, but this comparison misses the mark. In addition, dress shirts have specific characteristics that are good to know.
First of all, a dress shirt isn’t just any old button-up shirt. However, this gets confusing because many workplaces and events that require dress shirts might allow button-downs as substitutes.
For the purposes of this guide, we’ll assume that you need an actual dress shirt and not just a button-up.
Strictly speaking, a dress shirt is a structured shirt with a sharp, clean collar. The most common collar types for dress shirts are the point and spread collars.
Dress shirts also typically feature fairly plain fabric weaves (i.e., the fabric isn’t heavily textured).
Last but not least, dress shirts have solid-color or subtly patterned designs. Any so-called dress shirt with a loud or bold design or pattern isn’t a true dress shirt.
How Dress Shirts for Big and Tall Guys Should Fit
Lots of big and tall guys focus on finding the right sizes — and understandably so. But they often don’t pay as much attention to fit, an element that’s just as crucial as size. Both size and fit are crucial, so we’re going to look at both.
First, let’s look at size.
One of the most important things to be aware of is that dress shirt sizes often go off collar size. Sleeve length is also a critical element here.
When you shop for dress shirts, you’ll often see numbers in the teens like 16 and 18. These refer to the circumference of the neck. Larger numbers like 30 and 32 refer to the length of the sleeves.
Counterintuitively, the chest and waist measurements are derived from the neck and sleeve measurements.
There are some equivalencies between dress shirt sizes and normal shirt sizes, but these vary from brand to brand. For instance, a size 18 dress shirt is usually in the ballpark of an XXL (47”-49” chest). However, don’t rely on converting sizes, as this can be inaccurate.
This sizing scheme isn’t that helpful for big and tall guys. It’s especially bad for big guys who carry their weight in the stomach area.
For those reasons, you should always look at the full measurement list of a dress shirt. That includes chest size (pit to pit) and waist and shoulder width.
Perhaps most importantly, don’t be afraid to wear the size you actually are. Being a 6XL in a certain brand might not feel great, but at the end of the day, it’s arbitrary sizing. What’s most important is that your clothes fit you well — no matter what they say on the tag.
And speaking of fit, let’s talk about that.
Even if you nail the size, a dress shirt just won’t look right if the fit is off. Of course, a tailor can help with fit, but you might as well start with the best-fitting shirts you can find.
Obviously, fit will depend on the specific type of fit your shirt is. If you get a slim-fit shirt, for instance, it should be on the slimmer side.
But let’s start by looking at a classic or regular-fit dress shirt as a baseline.
In short, dress shirts for big and tall guys should fit somewhat closely and outline your silhouette without increasing it.
The exact way a dress shirt should fit will depend on where you carry your mass.
If you carry your weight in your belly, you’ll want to think about whether you want to try to cover that weight. If you do, look for a shirt that provides a bit of boxiness around your stomach to square it off. This will make it look smaller by effectively evening out your proportions.
Wearing your pants at your natural waist (instead of below your gut) also helps minimize the stomach area.
If you’re okay with having your shirt outline your belly, then you can go for a closer fit. It still shouldn’t be snug, however — you don’t want to pop buttons every time you sit down.
You’ll also want to make sure that your shirt stays tucked in. When you sit down or raise your arms over your head, your shirt shouldn’t come untucked. (Tall dress shirts will come in handy here, as the extra length will help them stay tucked.)
If you go with a more relaxed fit, keep in mind that you’ll probably need to get it tailored. (There’s more on that below.)
Unsurprisingly, big guys should generally avoid slim fits. This is true whether you’re chubby or muscular. The one exception here is if you’re tall and lean. In that case, you could go for a tall-sized slim-fit shirt.
Dress Shirt Tailoring for Big and Tall Guys
The reality is that you’ll probably need to visit a tailor to get any dress shirt to fit impeccably. This is especially crucial if you’re wearing it for a white-collar job or an important formal event. If you’re expected to look sharp, you shouldn’t turn up in an ill-fitting shirt.
Big guys will likely need to get the sleeves taken in, and they might also need the neck and shoulders adjusted. This will often be the case unless your weight is distributed almost perfectly equally.
For example, if you have a larger belly, a dress shirt that fits your stomach will likely be too big in the sleeves. Similarly, if you’re tall and have a large torso, you might need the shoulders broadened.
Thankfully, pretty much all clothing alterations are cheap. Once you find a tailor, the rest is easy. Your tailor will be able to make specific suggestions based on your body and desired fit.
It’s worth noting that if you do plan on getting your clothes tailored, err on the larger side when sizing. Tailors can make a shirt shorter and smaller, but without the same fabric, they can’t make it bigger or longer.
It’s incredibly beneficial to have a tailor as a big and/or tall guy. The sooner you have a good ongoing relationship with a tailor, the better.
Finding Dress Shirts for Guys With Big Bellies
Pretty much all of the guidelines above apply to all big and tall guys. However, there are a couple of specific demographics that tend to be the trickiest. One of those is guys with bigger bellies.
The best all-around option for a big guy with a belly is to buy a shirt that’s on the bigger side and have it tailored.
However, there are some ways that guys with big bellies can shop for dress shirts more effectively.
Secondhand shopping is an extremely effective approach. If you have a dress shirt that fits you well, you can measure it and compare those measurements to shirts when browsing. Secondhand shopping is also a great way to find brands that you can rely on for clothing that fits you well.
You should also look at brands that offer extended or big sizes, but make sure you check out reviews first. Unfortunately, a lot of the brands that target big guys make extremely low-quality clothing.
Also, keep in mind whether you need a big size or a tall size. As mentioned earlier, you might want to try out tall sizes if you need a shirt that stays tucked in.
Finding Dress Shirts for Guys with Big Necks
If you’re bigger around the neck and shoulders, then you’ll almost definitely want to get your dress shirts tailored. Whether you’re muscular or just big, you’ll likely have difficulty finding a shirt that fits perfectly off the rack.
Sizing up will usually allow for more room in the neck. However, this also means that the rest of the shirt will probably be too big. Similarly, if you buy a shirt that fits your chest and stomach, it might not fit your neck.
You might be able to find some better-fitting shirts if you shop secondhand. Overall, though, plan on tailoring.
Best Dress Shirts for Big Guys
Here are some fantastic brands that make dress shirts for big guys.
Proper Cloth
Want to invest in a high-quality dress shirt that will last for years? There’s an argument to be made for going made to measure (MTM). This approach, while often pricier, ensures that you get a fit that’s perfect for you.
Proper Cloth is one of the most popular MTM companies out there and for good reason. The brand offers a wide range of dress shirts, which means you can build your ideal shirt from scratch. There are also stretch options, which are great for big guys.
Brooks Brothers
For off-the-rack clothing, Brooks Brothers is a solid, reliable choice. The brand offers neck sizes up to 19 and sleeve sizes up to 38/39.
It’s worth noting that Brooks Brothers’s retail prices for individual shirts are pretty close to MTM. However, there are often sale prices or bundle discounts that make these shirts a better deal.
Ralph Lauren
You might not guess it, but Ralph Lauren actually has an extensive big and tall range.
The brand offers dressy options like the Gingham Stretch Poplin Shirt in sizes up to 6X Big and 5X Tall.
Charles Tyrwhitt
This classic English menswear brand has long been a go-to option for big guys seeking dress shirts. It offers neck sizes up to 20 and sleeve sizes up to 38.
The shirts are surprisingly affordable and very well made for the price. Plus, the multibuy offer allows you to save on larger orders.
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