StyleOtter | Men's Dress Shirt

The 101 on Men’s Dress Shirts and Styling Tips

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A dress shirt remains an iconic, classic foundational piece of any wardrobe.

The challenge, however, is finding a quality tailored dress shirt that not only looks pulled together, but also fits properly, and makes sense for the occasion. 

In this post we’ll cover off on classic dress shirts that we believe belong in your wardrobe.

In addition, we’ll also walk through a variety of different occasions for dress shirts to ultimately help you hone in on your personal dress shirt style. 

What is considered a dress shirt?

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Think of a dress shirt as your go-to shirt when you want to look pulled together, professional, and confident. 

Typically made of a woven cotton material, a dress shirt is most commonly a button-down with a collar (also known as an Oxford.)

Dress shirts are typically long sleeve, but can also be short sleeve depending on the fabric. 

Dress shirts are intended to be fitted shirts, so they look best when they’re the right size.

They also usually need to be pressed or ironed, but more on that later. Let’s learn more about the history of the dress shirt. 

A Look Through Time – A Brief History of Dress Shirts

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Dress shirts have always been particularly well known for their ability to be layered. And photos throughout history prove this to be true. 

At the beginning of the century, most dress shirts were typically covered up by heavier suit jackets. Two-piece suits were the norm, and it also wasn’t unusual to pair the outfit with a hat.

The dress shirt was rarely able to have a moment underneath heavier layers.
As the 1950s and 1960s progressed, men began to more freely wear dress shirts without layering a suit on top.

But it wasn’t until the 1970s that men’s dress shirts became, well, a little bit more personalized and unique. Clothing became a bit more expressive, and dress shirts were often paired with herringbone bell-bottom slacks. 

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image via flashbak

Sweater vests were also…a thing. 

Fast forward to the 1990s and early 2000s, the emergence of the even more casual dress shirt comes to fruition.

Dress shirts aren’t just one type anymore – they come in all different colors, sizes, materials, and vary in benefits (some are no-iron, others are moisture-wicking, and so on.)

It’s clear that no matter the decade, dress shirts are a timeless wardrobe item. So let’s talk about why you need the perfect dress shirt. 

Why Dress Shirts Are Your Secret Weapon

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Dress shirts are your secret wardrobe weapon and an absolute necessity, given there are so many occasions where dress shirts are applicable. 

Here’s how a classic dress shirt helps uplevel your style game:

  • Confidence
    • When a dress shirt fits properly and looks good, you’ll notice that you stand a little taller – because a well-fitted dress shirt is the ultimate confidence booster
  • Comfort
    • Having a perfect dress shirt that is the foundation of your wardrobe will help you feel comfortable in the rest of your outfit
  • Flexibility
    • Having a go-to dress shirt in your closet will ensure that you’ll be ready for any occasion

How to Get Fitted for a Dress Shirt

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Throughout this post, including measurement, we are specifically referencing long sleeve dress shirts. 

So, you might make it through this post and decide that you’re ready to purchase a dress shirt, even though you might be guessing on your sizing.

Our advice? Don’t do it.

It’s best to get the measurement part out of the way. Sure, it may be an inconvenience now.

But the truth of the matter is, it will save you time and money in the long run if you are able to take care of sizing upfront. 

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Getting fitted for a dress shirt

  • Step 1: Get your hands on some measuring tape
  • Step 2: Measure the base of your neck. Typically, this is the area where the collar of the shirt would sit. Ensure the tape gives a little extra breathing room so future collars aren’t too tight
  • Step 3: Measure your chest (having an assistant might help!) take this measurement around the widest part of your chest
  • Step 4: Relax your arms by your sides, and measure your sleeve, from your shoulder down. Keep in mind that you don’t want the measuring tape to start higher than where your shoulder begins to slope, otherwise you may wind up with a shirt that’s too tight
  • Step 5: As long as you have the measuring tape out, measure your waist at its widest point 

While many dress shirts typically involve neck and sleeve measurements, it doesn’t hurt to have extra chest and waist measurements just in case. 

You may also notice when shopping for dress shirts that there are also “fit” selections.

The above chart from UnTuckIT breaks down the different kinds of fits, so you can decide what might suit your body type best. 

Elements of a Classic Dress Shirt

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A classic dress shirt is: 

  • Not too tight or big
  • Easy to take care of
  • Simple in its colors/patterns – have a least one dress shirt in your wardrobe that you can wear alone or underneath suits/blazers
  • In a fabric that makes sense for its climate/environment (see below for more

The One Dress Shirt Every Man Needs

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Drumroll please….

There is one dress shirt that every man should have in his wardrobe (and quite frankly, women too!), so it should come as no surprise that a classic, crisp, white dress shirt is the ideal “starter” shirt for anyone looking to invest in their basics.

While white shirts may require more maintenance (i.e. staining or spilling), they will go with most of what you have in your wardrobe. 

Here are a few of our favorites based on different price points:

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How Much Should Dress Shirts Cost

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We’re lucky to live in a time where we can order any kind of shirt we want with the click of a button.

The downside, of course, is ordering online without testing the fabric, or trying on different sizes to see what’s best (keep in mind every brand has different fit charts/size guides that you should check before placing an order.)

In our experience, the lowest cost for quality dress shirts typically starts at around $40, and the pricier quality dress shirts can go all the way up to $500 and beyond. 

So spending upward of $500 is likely unnecessary. However, our recommendation is to try on dress shirts at varying price points to get a feel for what you like best.

You may find that investing in fewer, higher-quality shirts make more sense than buying a week’s worth of cheaper shirts.

Different Occasions for Different Dress Shirts

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Not all dress shirts are created equally.

In this upcoming section, we’ll be referring to shirts that are dressier, and some that are also on the casual side (think nicer button-downs.)
Let’s start with office style:


Business Casual: If you work in a business casual environment (think dress pants and likely a suit or dress shirt) stocking up on classics that you can wear Monday to Friday are ideal:

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Casual: As we mentioned before, it’s becoming more and more popular for offices to go more casual these days. This usually entails a pair of dark denim and a button-down. Here are a few options we love for the workweek:

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If you’re going on a date or meeting some friends up for drinks on the weekend, consider exploring the “Casual Office” suggestions above


If you’re a frequent traveler, there is one kind of shirt that undoubtedly belongs in your wardrobe – a no-iron, moisture-wicking button down. Plenty of brands carry these types of dress shirts nowadays, but here are a few of our favorites:

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Always check a wedding website or invitation before deciding what kind of dress shirt to wear. Sometimes, weddings are black tie, and other times you’ll be able to pull off a business casual look. Either way, this is where a white shirt comes in handy – no need to invest in multiple different looks for this category

How to Style Your Dress Shirts

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Now that you’ve given your dress shirt style some thought, the next question is – what do you pair with your dress shirts? 

First, let’s start with color pairings. Not all colors go together, so here are a few ideas when you’re thinking about how to swear specific types of patterns and colors together.

  • Color pairings:
    • Black and white with denim
    • Navy slacks and white dress shirt
    • Pattern with dark denim or navy dress pants
    • Olive green slacks or jeans with white dress shirt
    • Khaki shorts or pants with white dress shirt

Now, let’s review different types of bottoms and how they can be styled with a dress shirt. 

  • Slacks
    • Slacks are a classic pairing for a dress shirt, and a well-fitted pair of dress slacks will bring your entire look together
    • We’d recommend this brand for their custom tailoring, reasonable price point, and variety of colors, but any fitted pair of slacks that are the right length will look great with a pulled together dress shirt
  • Jeans
    • The denim and dress shirt combo is the perfect blend of casual meets professional. A great outfit for the daytime or date night, denim perfectly complements a more fitted dress shirt
  • Shorts
    • While likely not as common as slacks or jeans, the right pair of shorts can still look pulled together when combined with a dress shirt

Don’t forget adding the finishing touch to all of these bottoms: a belt. Particularly, a good quality leather belt that will last for years to come

Often times, a leather belt can break up dress shirts and bottoms that may not actually look like they belong together. 

Otherwise, a belt is the perfect accessory and finishing touch to a dress shirt look.

Still looking for more inspiration? We also talk about more of our favorite pairings in this post about men’s must-have basics.

How to Care for Your Dress Shirts

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We believe that taking care of dress shirts is a bit more straight forward and won’t typically necessitate a trip to the dry cleaners. 

  • Spot Treating
    • It’s time to make a stain pen your best friend. Keep one handy in your messenger bag or backpack for on-the-go treatment, so that you’re not waiting for your shirt to go into the washer to get a stain out (by then, it might be too late!)
  • Washing vs. Dry Cleaning
    • Let’s face it, dry cleaning isn’t easy on the wallet – and it may not be “cleaning” your shirts like you’d expect. When in doubt, consult the label on your shirt for the best care
    • Ditch the dryer – not only will a dryer cause colors to fade over time, but the heat may also cause your shirt to wear faster than if you were to hang dry
  • Sweat Stains
    • No shame here. Sweat stains happen, especially when it comes to white dress shirts
    • Your best bet for treating sweat stains is to remove your dress shirt, apply vinegar to each underarm of the dress shirt and let sit for 15 minutes, then soak the shirt with a cap full of regular detergent for another 20 minutes before tossing into the wash
    • Whatever you do, don’t put your shirt in the dryer after treating, as this will set the stain. Instead, hang dry
  • Ironing
    • We cannot stress this enough: an ironed dress shirt is a dress shirt well worn. Don’t get lazy with ironing – it can make or break the look of the shirt!
    • The pro of using a dry cleaner is that dry cleaners will press your shirt. However, you can still press your shirts at home with the right tools
    • Invest in a quality clothing iron, or our favorite, a steamer – just don’t steam while you’re wearing your shirt!
      • We also recommend this video if you need some help ironing your shirts
  • Folding vs. Hanging
    • Dry cleaning your shirts? Keep them hanging when you bring them home
    • If you have shirts that are non-iron, keeping them folded in your dresser is an easy alternative to hanging 
    • Need tips on folding shirts? Check out this tutorial
  • Traveling with Dress Shirts
    • If possible, keep your shirts hanging. This method works mostly for road trips
    • If you’re flying and you’ll need to pack your shirts, call ahead to your hotel or host’s house to see if an iron is available. Pro tip: if you’re staying at an Airbnb, these amenities will typically be featured in the listing
    • If an iron isn’t available and you have extra space, consider investing in a compact steamer, especially if you have room to spare
    • Lastly, if you’re flying and plan on carrying on dry cleaned clothes separately from your carry on luggage, it will count as extra luggage


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Is a polo a dress shirt?

In our opinion, a polo is not a dress shirt. Polos are typically short sleeve, and are made of a different kind of cotton than what we would consider to be a dress shirt. 

With that said, polos are great for more casual settings, but we wouldn’t recommend wearing a polo to an event like a wedding, or counting a polo as business casual dress. 

How can I prevent sweat stains?

  1. Try wearing an undershirt under your dress shirts to provide an extra leg of defense
  2. Watch the aluminum in your deodorant – this is an ingredient said to create more sweat stains. Instead, try investing in a clinical strength antiperspirant 
  3. Shave or trim your armpit hair
  4. If stains develop, wash your shirts right away 
  5. If all else fails and you’re still sweating, talk to your doctor or dermatologist about excessive sweating treatment
  6. Try to not get nervous about sweat stains – your anxiety is likely contributing to your sweat!

Can I roll my sleeves up?

Yes, rolling the sleeves up of your dress shirt is an easy way to pull off a dress shirt in a more approachable manner. Just make sure if you’re rolling your sleeves up that the rest of the shirt doesn’t end up wrinkled. 

We recommend one or two folds up from the wrist for a more casual look. 

Should I choose patterns for dress shirts?

Sure, why not? We love a good pattern on a dress shirt. However, if you’re looking to invest in quality over quantity, consider buying dress shirts that can be styled in different ways, and go well with the rest of your wardrobe items (including pants.)

Should I bleach my white dress shirts?

In our opinion, we believe that bleaching white dress shirts actually make sweat stains, and other stains, pop more (yikes.) Bleaching your socks and white cotton tees? Fine, but keep your dress shirts separate. Also, remember to keep in mind that sweat stains don’t just happen overnight (especially sweat stains) so the sooner you’re able to wash your white dress shirts, the better!

Should I wear my dress shirts untucked? 

It’s up to you, but in our experience, it depends on the scenario and your audience. An untucked dress shirt may work for grabbing beers with friends, but if you’re looking to appear more professional and pulled together, we’d recommend tucking in your dress shirt. 

Another classic way of wearing dress shirts is pulling a French tuck, recently made popular by Queer Eye for the Straight Guy. 

Are short sleeve dress shirts acceptable? 

Define acceptable. Similarly to our answer about polos, above, short sleeve dress shirts have their moments. For example, if you’re vacationing in the Bahamas and want to wear a white linen shirt that appears to be a little bit dressier, knock yourself out. 

However, that same shirt may not be suitable for a board meeting at work. Know your audience and know the scenario to decide whether or not a short sleeve dress shirt is acceptable. 

Otherwise, we do have a few picks for short sleeve dress shirts if you’re seeking recommendations: 

Final Takeaway: Dress Shirts Help You Dress to Impress

Dress shirts are your secret weapon. With a few quality dress shirts in your arsenal, fancy events, weddings, and dates will be no match. 

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