10 Shirt Styles Every Man Should Know & Have in Their Wardrobe
When is a shirt not a shirt? Today, the helpful team from Oliver Wicks digs deep into the world of men’s shirt styles, how they differ, when to wear them, and why there’s such variety in the first place. Ready to answer all those shirt-related questions you have? Let’s go!
So, what’s popping in the shirt world? Let’s take a look at some common shirt styles you will run into. Remember that people often reference collar styles, too. Dress shirts and office shirts can use several collar types, while still being ‘the same thing’, so don’t let that throw you off your game.
Ok, we’ll admit it - we made that up. Terms like these, however, you’ll see used as a catch-all for shirts you’d wear under a suit or blazer, but there’s a ton of sub-classes that all fit in here.
In general, a ‘suit shirt’, or a classic man’s shirt, will be made of a robust cotton for breathability. Cheaper shirts can be made of polyester, but they’re a bad buy, being uncomfortable and looking cheap to the eye.
All classic shirts have long sleeves and proper cuffs, most often the stiff and one-layer barrel cuff. These cuffs will fasten with a button or similarly mounted closure, rather than needing cufflinks. Cufflinks are your first clue it’s a dress shirt. Some high-end or bespoke suit shirts use cufflinks, but that’s often a personal preference chosen in bespoke shirts by gents with their own style.
In this category, we have button-up shirts and button-down shirts. A button-up shirt is just another way to say a shirt for a suit - it has buttons in the front you use to close the garment. Button-down shirts have buttons on the collar which… you guessed it… button-down after you tie your tie. They’re a bit more casual than a button-up shirt with a regular collar, but they can still be worn in professional environments.
Button-up shirts can be worn without a tie, or have the sleeves rolled, in the right setting, but check the collar style carefully if you want to skip a tie, as some shirt collars are a bit thin and floppy, and you may have a hard time trying to get it to sit neatly (this is often a reason why some men prefer button-down collars!).
The Oxford Shirt pairs brilliantly with a suit, but they’re also highly versatile and can fit in with casual wear, daily office wear, and even weddings if you’re careful with your selection. It’s made from so-called Oxford fabric, which is cotton with a basketweave, so it’s a little thicker and softer than cheaper cotton. Oxford shirts usually have button-down collars, too, although you will get some without. A hanger loop at the back of the yoke is pretty standard, as well.
If you want to dress sartorially, or just embrace true masculine elegance, this is a shirt you need in your wardrobe. Most snappy dressers default to an Oxford shirt in a color of their choice for daily wear.
Dress shirts are used in more formal fashion and eventing - like black tie, or weddings. Typically made of cotton, they close at the cuff with cufflinks. Instead of the starched barrel cuff, they have double cuffs which you fold for this purpose. They usually have fancier collars, too, with cutaway, wing, and pointed collars being typical. They’re absolutely essential for white and black tie eventing, and it’s great to have a crisp white dress shirt in your wardrobe for weddings and formal occasions.
Cotton short-sleeve shirts were once a fashion crime that screamed ‘blue-collar worker’. Nothing wrong with that, of course, but you don’t want someone you’re meeting for the first time to assume you are their DoorDash delivery guy. The short-sleeve shirt has been reinvented by designers recently. It’s still a style best kept for the odd outdoor activity or a hot and casual day out, rather than daily dressing. It can be acceptable corporate workwear in some hot climates but check your work’s dress code first.
You distinguish them from polo shirts and tee shirts because they button-up and have a collar. Some people wear short-sleeve shirts with a tie, as if it were a regular professional shirt, but we’re not at all keen on this, from a classic, formal menswear perspective They can be excellent for casual cafes and beaches, where you’d expect the wearer to leave the top button undone in a relaxed manner.
Short-sleeve for the business/professional world? We’d give it a miss!
The Cuban Collar shirt is a specific type of short-sleeved shirt with, of course, a Cuban-style open collar. This can make them great to showcase a chunky necklace or similar jewelry. They typically have patterns and bolder colors. Styled wrong, they can have a bit of a ‘dad taking the kids on holiday’ look, but with a smart eye for balance, some suave looks have been made with these shirts. They really are best for hot climates or seasons, though. Wear them anywhere casual.
T-shirts come in a huge range of styles, often named according to the way the neck is designed. So you’ll hear crew-cut (has a circle neckline called crew neck), v-neck (a sharper neckline), deep v-neck (best reserved for women), polo neck (with a roll of fabric), boat-neck (a wide and shallow neckline mostly used by women, but present in some fashion for men), and so on. Henley T-shirts have a y-neck, which means a circular neck and a few buttons. They’re typically cotton or cotton-blend, and have no front closure. The crew-neck tee is the ‘standard’ tee we are all familiar with.
Most tees have short sleeves, although a long-sleeved tee can be versatile under knitwear in winter. A long-sleeved polo neck (not to be confused with a polo shirt) makes for fantastic winter and business casual looks. Some smart-casual looks can make great use of a crisp tee in high-quality cotton, but they’re not suitable for more formal wear. Styled with a good overshirt, you can make a comfortable t-shirt look good enough for daytime smart-casual. Worn alone, they should only be for the home or a quick run to pick up the kids or to buy groceries.
As with any menswear piece, finding a t-shirt with a great fit is very important, as it can totally make the difference between smart-casual and ‘teenage skater boy’.
Polo shirts are a special type of T-shirt, typically made from cotton and polyester blends. They have a stand-up collar, and usually a few buttons at the neck, but don’t need to be buttoned up to close. They’re a compromise between the formality of a shirt and the informality of a T-shirt. They also look great in a sporty look - named ‘polo’ because they’re part of the standard polo uniform!
While certainly not on the same formality radar as what you’ll find at Oliver Wicks, polo shirts certainly deserve a place in a stylish gentleman’s casual collection. They’re also a great compromise for anyone that finds standard t-shirts just a little too casual.
Polo Fashion Sins:
- Never button up the top button!
- Never wear your polo collar up!
Both of these ‘crimes’ are extremely tacky, and far away from the grounds of being a respectful gentleman.
Fashion magazines and websites often break down shirts by their fabric - ones that are not the classic cotton suit shirts. Each fabric brings its own character to the table, but many carry some stereotyping, too, so bear that in mind when using these. It can be fun to play with those stereotypes, but you don’t want to look gauche wearing them in the wrong place! They’re rarely a good choice for dressy occasions, and most lean very casual. They can be used as great overshirts, though, paired with the right pants and accessories.
Flannel shirts are made of flannel and carry the ‘lumberjack’ near-tartan patterns. Denim shirts are denim, of course, and can be ultra-stylish or very sloppy, so tread carefully. Chambray shirts are like lighter, finer denim, which makes them incredibly versatile and a bit more stylish. They even transition well to smart-casual. Linen shirts are another high-end choice in this category, with fantastic potential for hot weather smart-casual.
Overshirts are, literally, a shirt deliberately worn open over a tee or another shirt in cooler weather. Many Fabric Shirts make a great overshirt, as will anything with a thicker cotton that can be convincingly worn unbuttoned and still retain some structure.
Again, this is very much a casual look. One important note about the fabric thickness that we just mentioned, is that an overshirt should be substantial enough that it is not transparent in any way.
This is a newer style of men’s shirt (in the West, at least) that still brings plenty of structure and style to the table, but is a little more relaxed and less constricting. It’s classy enough for some formal eventing, eye-catchingly different, but still has clean lines and intention behind it. It’s designed a little like the Henley T-shirt, with a small number of buttons at the neck to mid-chest. While it is long-sleeved with a collar, it has the shape of traditional Asian and African garments instead of the T-shape of a Western shirt. The collar is also a flatter band, rather than the pointy collar you’re used to. The hem is often curved at the front and back, too.
Of course, it’s impossible to wear a tie with such a collar, so by default, this option can be ruled out for a lot of professional environments.
Now you know how to tell the style of a shirt (and where to wear it), let’s look at some common questions about shirts.
Tees win hands-down in this category if you’re wearing them by themselves. However, with intentional styling and a good fit, you can upgrade a good tee to smart-casual looks. If you want a presentable, but casual, look that suits hot climates, try the Cuban Collared shirt, or a polo. We’d recommend avoiding big logos or slogans, as they instantly make a garment look extremely informal.
An Oxford button-down shirt is a must-have for any man. Practical and versatile, it will take you everywhere and look stylish along the way. If you’re starting your wardrobe, start here. It will be an investment that pays off in spades. Cotton is ideal for daily wear comfort, and in the hotter months, linen shirts are a great investment to beat the heat.
First up, absolutely nothing looks good if worn in the wrong place or season, making you look gauche. So always consider function, formality, and weather when deciding what to wear! Then, choose a shirt that fits your body type well.
Remember, there’s a reason we talk often about tailoring on the Oliver Wicks blog, and why we say it is all about the fit - ‘the fit that suits you. Something that fits you perfectly has a style and suaveness you can’t get with a sloppy compromise. That’s why we employ only master tailors for our suits, and shirts! Check out Oliver Wicks custom suits and be sure to reach out with any questions at firstname.lastname@example.org.
While shirts can be more forgiving, allow yourself to experiment with fits and judge what suits you best. Most modern men’s garments fall in classic, slim-fit, and modern tailoring. Classic is loose, while slim fit is very tight to your body. Most men should start with a modern fit, and see what they like from there. Yes, that goes for husky men, too. A good modern fit will often look far better, and slimmer, than tons of excessive fabric, so don’t hide away.
When it comes to shirts, a lot of men have an unnecessary desire for ultra-slim-fitting garments. Overly slim shirts are not only restrictive and uncomfortable, but they’re also just a bit naff, a fashion trend that came and then dissolved. A modern fit that compliments your figure, rather than restricts it, we feel, is a much more gentlemanly way to go. Also, it’s very simple for a tailor to add darts to an existing shirt, so there’s always a way to slim down a shirt, but it can’t be done the other way if you’re starting with a slim shirt.
When in doubt, go for a nice soft, yet robust, cotton with a great feel. It’s the perfect blend of drape, breathability, versatility, and length-of-wear. It also looks classy to even the most untrained eye. Even some cheaper cottons and blends can look good when well-cared for, while high-end cotton is a classic.
Linen shirts are highly breathable, with excellent comfort, so these are a great choice if you live in an area that has very warm summers.
It can be tempting, especially on a budget or when purchasing for a one-off event, to opt for a cheaper fabric. However, man-made fabrics easily become sweat traps, and there’s nothing more ugly than pit stains on show! Nor do you want to feel like you’re encased in sweaty layers, pulling at your collar, instead of living your life.
If you’re not up to ironing your cotton, invest in a garment steamer. There are cheap models available, and they’ll banish all wrinkles easily. Alternatively, many professional laundry services are very affordable, but we suggest being careful with who you choose to trust with your nice shirts.
If you can easily fit a custom shirt, or three, into your budget, absolutely go for it! Having a custom-made or bespoke shirt ensures that the fit is always perfect for your body and all its natural idiosyncrasies.
However, an off-the-rack shirt won’t always be a bad purchase. Tailoring will give you some ability to tweak the fit, getting the best possible fit at the collar, and across the shoulders. Next consider length, and how it fits at the barrel of your chest. Don’t be afraid to be a bit picky - it might feel alright for two minutes in the shop, but you don’t want to be annoyed when wearing it all day.
As with suits, there are many gentlemen that struggle to find an all-round well-fitting shirt from a store. For example, some guys have wider necks, and need to size up in order to wear a tie comfortably, but they’re left with a loose fit in the belly as a result.
Made-to-Measure shirts are the perfect solution for such cases, as we believe that all men deserve a great fit, without having to compromise.
As you can see from our list, nope! Formal functions call for a closed-neck with a tie or bowtie, whereas you can get loose and bold with open collars and rolled sleeves in smart-casual and daily styles.
With our traditional views and styling as tailors, we’ll always vote in favor of wearing a tie whenever the question comes up. Afterall, you’re probably drawn to Oliver Wicks because we stand for making the extra effort to dress well, and a tie with a perfectly presented dimple is a clear way to demonstrate your exquisite taste in formal attire. It’s like watching your grandfather polish his boots for hours on end… Sure, it’s not totally necessary, but you respect him for it, and appreciate his faultless appearance as a result.
Remember - If you start the day/event with a tie, you can always take it off. If you’ve not got one with you, you can fall into a situation where you may wish you’d worn one.
There you have it! With this easy guide to shirt styles in your back pocket, you’ll always make the perfect match to your look and the function. Don’t be afraid to experiment with different shirt types and make yourself a personal style you can be proud of no matter where life takes you.
Looking to invest in some stand-out shirts to complete your wardrobe? The Oliver Wicks team is always on-hand to help you find your perfect fit, so don’t hesitate to reach out today. Our no-obligation newsletter is packed with helpful tips like this, if you’re keen to get added to the list. Plus, instructional videos, measurement videos, and many other resources are available when you create a free account on our website (no purchase obligations).