The Perfect Fit: Dress Shirts

by Beau Hayhoe  |  in Business Attire

We’re here today with the latest entry in our ongoing series – The Perfect Fit. Last time we covered how your suit trousers should fit.

Luckily for those who like putting complete outfits together in a cinch, today we’re looking into how a dress shirt should fit.

Even if you don’t wear one every day, it pays to know how to wear one – and how a dress shirt should fit your body.

If you are in the habit of wearing a dress shirt daily, you could use a refresher on key men’s style essentials.

Coming from a guy who dresses casual day in and day out, it helps to get reacquainted with dressier style principles from time to time. Once you’ve got down the basics of how a dress shirt should fit, it’ll always be top of mind.

That same dress shirt can team up with a stylish V-neck sweater, a classic winter suit or a slim summer blazer with ease.

But’s let back up a few steps and make sure that your shirt’s not wearing you. On the contrary, we’ll help you achieve that hard-to-find perfect fit.

How Should My Dress Shirt Fit?

Look around any office and you’ll see varying examples of poor dress shirt fit:

  • Too baggy
  • Too loose through the arms
  • Too tight around the shoulders

We’re going for the sweet spot in terms of fit, though. Tailored, yes. But not skin-tight.

Oftentimes, shirts are too long or baggy through the middle. You should aim for a dress shirt that, when tucked in, doesn’t billow because of excess fabric. The same general rules of fit apply to dress shirts and sweaters.

Our man Dwight Schrute is not someone to emulate for how a dress shirt should fit.

Dialing in the fit through the chest is crucial. This helps ensure the rest of your shirt has clean lines.

A higher armhole prevents excess fabric on the top half of your body. Again, we’re going for tailored, not tight.

Through the arms, you want a dress shirt that skims but doesn’t cling. A fit that’s as tight as a T-shirt around your upper arm won’t do.

Aim for a happy medium – take, for instance, actor Eddie Redmayne. Although he’s wearing his crisp white shirt in casual fashion, it’s trim through the sleeves and waist, avoiding excess fabric throughout.

The Perfect Fit: Dress Shirts

Finding the perfect fit for your dress shirts might take some experimentation. If you hit the gym a lot, a size Small shirt in a slim fit from a retailer like Bonobos will fit you differently than, say, a menswear writer like myself.

That’s why knowing your measurements is so important. You’re going to want to know both your neck (circumference) and sleeve (length) measurements when shopping.

Big-name, trusted brands like J. Crew offer dress shirts in sizes Small through Extra Large. Sizing charts come in handy. And never rule out trying on a shirt or two – or three.

There are other methods that aim to be error-proof. For instance, custom shirt-makers Black Lapel can match the fit of your dress shirt to the precise measurements you give them.

The Perfect Fit: Dress Shirts
via Black Lapel

More on that later. For now…

Think Of It This Way:

  • Minimize excess fabric through the waist and sleeves
  • A higher armhole creates clean lines
  • Don’t go too tight or too baggy

What To Avoid

When shopping for dress shirts and trying to find that elusive perfect fit, beware this trap:

Current fashion trends generally dictate that tighter is better. But a dress shirt that’s too tight becomes nearly unwearable.

There’s a difference between a skin-tight fit and a tailored fit. Daniel Craig gets it mostly right, even if his shirt’s a little rumpled.

You might argue, “If I’m wearing a jacket, why does it matter how my dress shirt fits?”

A well-fitting dress shirt opens up versatility. It should fit so well that you you can wear it sans jacket, sleeves rolled up, ready for business ( like the impeccably tailored Hugh Jackman).

The Perfect Fit: Dress Shirts

Don’t make the mistake of thinking a jacket can hide all your style sins, either. Instead, let’s nail that perfect fit.

It’s all too easy to go hog-wild and buy up handfuls of dress shirts on the cheap in an effort to find a great fit. Retailers who specialize in “fast fashion” should be avoided.

These brands make their clothing on the cheap, using lower-quality fabrics. That results in dress shirts that don’t fit, wash, or wear well.

Reputable brands like Ledbury specialize in excellent tailored wear and can even help you stock up on other style essentials.

There’s also some debate over the quality (and safety) of non-iron or wrinkle-free dress shirts. That’s because they’re usually treated with a chemical like formaldehyde.

However, brands such as Twillory are bucking the trend by making shirts that wear better and last longer. For instance, the brand’s SafeCotton shirts are made without dangerous chemicals.

Is there anything better than a crisp white dress shirt with a standout fit – courtesy of neck and sleeve measurements? Not quite.

Remember, the road to a great fit is filled with pitfalls. Watch out! Avoid the common mistakes most guys are making and nail the fit of your dress shirt.

Think Of It This Way:

  • Don’t buy too tight – go with a tailored fit for your body that allows for easy comfort with or without a jacket
  • Avoid “fast fashion” brands that use cheap fabrics
  • Look out for non-iron dress shirts treated with dangerous chemicals

How Should I Wear My Dress Shirt?

You’re stocked up on crisp, classic dress shirts from trusted retailers like Bonobos or the budget-friendly Uniqlo. Now, how are you going to wear that shirt?

As all of us EG readers know, starting with great fit makes things easier in terms of styling potential.

The Perfect Fit: Dress Shirts
via Bonobos

If you’ve got a clean and crisp dress shirt, you can style it with ease under a stylish V-neck sweater and alongside versatile suit trousers for an everyday tailored look. Maybe finish it off with suede Chelsea boots.

When the occasion calls for a tailored ensemble, your well-fitting dress shirt is going to do some damage. Combine your dress shirt with a tweed blazer at the office or on a more refined occasion.

Ties and other accessories are an entirely different ball-game. It all depends on the type of dress shirt you’re wearing. Still, that doesn’t mean fit falls by the wayside.

Keep your fit dialed in. Here’s a quick crash course:

  • If you’re wearing a classic blue or white dress shirt in a cotton fabric, a slim black or navy knit tie is the ultimate finishing touch.
  • Silk ties are another good, classic option – but beware the trap of always reaching for a predictable red silk tie. Like a certain political leader…
  • A slimmer, subtler tie – like a navy knit tie – makes it easier to ditch your jacket and roll up your sleeves – provided you’ve got the right fit.
  • If you’re wearing a dress shirt with a rougher fabric, such as a chambray dress shirt, a tie with a more substantial texture (like wool) will play off the shirt nicely.
  • You want to tie a knot that’s about the same proportion as your shirt collar. For more, check out the tie knots we suggest (you really only need to know these two).

Of course, you’ll want to make sure your shirt plays nicely off your suit jacket or blazer. That means the suit jacket’s lapels are about the same width as your shirt collar (note how the width of James Bond’s collar matches his suit jacket lapels, for example).

This is just the tip of the iceberg. There are plenty of variables in terms of accessories to match with dress shirts. But keep this in mind: It all starts with great fit.

Think Of It This Way:

  • Styling your dress shirt with everyday classics is easy if you start with the perfect fit
  • Look for accessories that complement the weight, texture, and color of your shirt
  • Match the proportions of your dress shirt‘s collar with your jacket and tie

Start with The Basics

The more you try your hand at perfecting the fit of your everyday essentials – and it’s still something I struggle with from time to time – the easier it becomes to build upon those principles.

Start by learning how a dress shirt should fit. That will lead you to a better-fitting blazer. That gives you more confidence at work…

You get the picture.

Perfecting the fit of your dress shirt is like any other basic item. If your dress shirt fits as well as your favorite T-shirt, you’re going to be more comfortable wearing it and more open to styling it with your favorite essentials.

Sometimes, the smallest building blocks make the biggest impact – especially in terms of style.

What are your go-to dress shirt brands? How do you style your dress shirt in unexpected ways?