For many men, dress shirts are an essential part of their wardrobe. It’s probably one of the first things they put on in the morning before they go to work.
There’s an endless choice between colors, fits, collar styles, cuff styles, and lots of other details that you can and must choose. At the moment, I have about 100 dress shirts in my collection and over the years, I had many more. I sold them and got new ones and so I learned a thing or two about dress shirts.
1. Pink Shirts
In my experience, pink shirts or a hit or miss. They can look well if you have a good tan and if the pink is quite light. They look really bad if it’s a strong pink and if you choose the wrong accessories. Most people don’t associate the color pink with masculinity and so if you wear that color, you definitely make a statement. In my experience, pink works against you and is overrated when the only purpose of wearing it is to get attention.
On the other hand, if you wear a very pale pink shirt because it’s part of the combination, it’s softer than a white shirt and it just shows that you’re comfortable with the way you wear it, then it can actually work in your favor. If you decide to wear pink shirts, try to stay with solid colors that are very pale, avoid bold pink stripes because that’s over-the-top in terms of color and pattern. Also, if you want to wear pink shirts, make sure to tone down the other items in your outfit specifically the accessories.
2. Extreme Cutaway Collars
These white collars have been quite popular with brands like Ralph Lauren, they are still around today and people wear them a lot. It’s definitely an extreme look and if you wear a neckwear of any form, it just doesn’t work in your favor. If you go with a regular necktie, you can see the band on the side and just looks odd unless you tie an extremely big Balthus knot which ends up in a very short tie, which looks odd too.
If you wear a bow tie, on the other hand, the bowtie usually covers up the area of the collar so you can’t really see the extreme cutaway style of the collar. When you wear a suit with a dress shirt in that collar and a tie, you truly create Vs or inverted Vs. When you have this extreme cutaway collar, it kind of throws off that balance and usually, it looks odd. I definitely have a few extreme cutaway collared shirts in my wardrobe but I find that I usually only wear them without a tie or with a bow tie because with the regular tie, it just looks weird.
3. Non-Iron Shirts
I get it, most men think of ironing shirts is a huge pain in the behind, so of course, if someone promises you a non-iron shirt, you are naturally interested in it. The problem is most dress shirts are made out of cotton and cotton inherently wrinkles. To prevent cotton from wrinkling after it’s being laundered, you need to really work on the fiber itself and treat it with many chemicals including formaldehyde. Now when you do that, even a high-end cotton doesn’t stay soft and luxurious anymore. It becomes cheap and also less absorbent. It almost has a plasticky feel and touch. The problem is when you wash the shirt a dozen or two dozen times, the non-ironing properties are literally washed away and you still end up having to iron your shirt in order to get a clean, crisp dress shirt.
The only company that I’ve found that provides a shirt that stays wrinkle resistant for a long time, which doesn’t mean it’s non-iron, but you need to iron it less is from Eton in Sweden. Unfortunately, these shirts cost about $300 each or more which makes it unaffordable for most men out there. In collaboration with the high-end Swiss shirt cloth maker Alumo, they’ve developed an exclusive process that allows them to create a wrinkle-resistant fabric that has fewer chemicals than a cup of black tea. I do have one of their shirts and I’ve had it for years and it really does a good job so when I travel and I need something where I know I may not have the chance to iron, I bring it along, otherwise, I stick with regular shirts because again, you get a custom shirt that costs less than an off-the-rack shirt from Eton.
4. Visible Monograms
Originally, monograms on dress shirts or garments were used to identify the owner. Oftentimes, people had staff and shirts were usually white so it was hard to determine whose shirt it was. A little monogram on a shirt told the valet whose it was and so everyone would have the proper shirt that they could wear and that would fit. In recent years, online custom shirts and regular custom shirts have become increasingly popular which provided the option to add monograms. Now for a lot of people, this is kind of a status symbol and they want to show off that they’re wealthy enough to afford a custom-made shirt or a shirt that was made for them.
Back in the day, a shirt monogram was stitched either by hand or by machine at around your waistband so it was never visible to anyone. It was simply there for the people who did the laundry and your valet. Today, people are placing the monogram on their shirt cuff, ideally in a contrasting thread, so everyone can see that they can buy a bespoke shirt. In my opinion, it’s gaudy on the one hand and showing off is never part of a gentleman’s personality. Now, there’s nothing wrong with having a shirt monogram; if you want to have that, I suggest getting it in the original place which is just on the left side on the waistband around that level. You can also get into tone in tone so if you have a white shirt, you can get a white monogram, so only you know it’s there and no one else. Maybe you could even have it monogrammed on the inside of your collar band, that way, no one will ever see it other than you and your partner and it’s a nice thing to have but it’s not showy at all and very gentlemanly.
5. Bold Printed Patterns
I’m not talking about stripes or classic patterns like checks, I’m talking about bold floral and paisley prints which have become increasingly popular in recent years. Technological advances and changes in fashion have allowed dress shirts to become a lot louder and more vibrant. I think it’s a trend that won’t stick around and it’s something that is popular now but probably 10-15 years from now, other things will have come and gone, but your solids, your checks, and your stripes, will remain in your wardrobe, you’ll be able to wear them, whereas the floral print is probably something that would look very dated at that point.
6. Dress Shirts That Are Meant To Be Worn Untucked
Honestly, I see it all the time when I go to parties or in the airplane catalog. People promote and wear dress shirts that are not tucked in. Now traditionally, a dress shirt was cut so it was longer in the back and front so it was less likely to come untucked, but it is also shorter on the sides so it looks extremely unflattering when it gets untucked. For example, if you want a summery casual linen shirt that you can wear untucked, you want a hem that is cut evenly, however, there are a lot of people out there who want to wear dress shirts but want to appear more casual and then they wear these untucked shirts in combination with a jacket and it just looks weird.
Why? Because the shirt sticks out from underneath the buttoning point which is never advantageous. Personally, I don’t like untucked shirts and even my summery shirts are ones that I can tuck in but I wear with a belt because it provides a visual contrast that is pleasing to the eye. My long torso can be shortened by creating a visually longer leg line. So if you want to wear shirts untucked, I suggest to go with polo shirts and to stick with tucked in shirts when you go with dress shirts. If you want to go with untucked shirts, keep it to very casual occasions and never pair it with a jacket.
7. Jewel Tone Dress Shirts
What I mean by that is very extreme and bold colors that I usually see worn by men who are very new to clothing who think they need to make a bold statement with the choice of shirt color so they end up getting a vibrant ruby red shirt, something that is extremely pink, turquoise, blue. It’s very vibrant and may be suitable for a techno party but it’s nothing you should ever add to a classically inspired wardrobe. Why? Because they’re too bold, they’re hard to combine with other accessories and they simply scream cheap and I don’t know what I’m doing.
8. Short-Sleeved Dress Shirts
If you live in a warmer climate or you suffer from hot summers, you may be prone to wear a short-sleeved shirt underneath your jacket. The problem is you won’t see the sleeves and so it would always look weird and orphaned because traditionally, a jacket looks better if you show a little bit of shirt cuff that usually matches the amount of shirt collar you see in the back of your jacket. On top of that, wearing a short-sleeved dress shirt with a necktie makes you look like a little schoolboy.
In my opinion, there’s not a real place for short-sleeved dress shirts in a man’s wardrobe because if you want to go casual, opt for a polo shirt or maybe a Henley shirt. Both of them are short-sleeved, you can get them with a proper collar even like a shirt style collar, and they are something that just looks good, they’re meant to be worn that way. A dress shirt, on the other hand, usually has sleeves, it has the button front. If it’s too hot, you can just roll up your shirt sleeves and you can roll them back down. So actually, there’s no real need for short sleeve dress shirt unless maybe you’re a four-year-old boy.
9. Pastel Colored Dress Shirts
Most men out there buy white shirts and light blue shirts. While white and blue built the foundation of any gentleman’s dress shirt closet, pastel colors can really help to add a note of individuality to your outfits without being over the top. When I say pastel, I mean tones that are very soft and just have a hint or a hue of color that is different than white.
For example, you can go with a very pale yellow, a pale green, a pale pink, a pale lavender, and these tones help to tie together accessories and overall, they’re very easy to combine, they make your outfits, your suits, and accessories look different without being over-the-top. You can also wear it with much more casual combinations such as a sport coat or a tweed coat where a white dress shirt would be too stark and would provide too much contrast.
10. Striped Dress Shirts
Stripes are very popular in dress shirts for men, particularly some that come in blue on a white background, or maybe in white on a blue background. You can find them in slightly different sizes going all the way from superfine to medium to bolder but it’s very hard to find a bolder stripe in a different color or a bolder stripe that is just much bigger. Usually, you have to go custom but once you have shirts like that in your wardrobe, it’s really easy to spice up that solid suit
So if you have a lot of solid jackets in your wardrobe, I strongly suggest investing in a few bolder striped shirts. If you don’t know where to start, I suggest going with a white and blue stripe that is bolder because that’s closest to what most people are comfortable with but then down the line, I really encourage you to be a little more daring and go with different colors such as green, orange, or yellow.
11. Winchester Shirts
What I mean by that is a shirt with a contrasting white collar on a different colored shirt body. That can either be a solid such as gray or it can be a stripe but the mix of that white collar gives you the resemblance of a classic white dress shirt and when you wear a jacket, you only have that V that shows a little bit of the stripe. You can either have the cuffs be matching the collar in white or have the cuffs match the shirt body; the choice is up to you.
Personally, I prefer having matching cuffs and collar that contrasts the shirt body. Winchester shirts are particularly suited for businesswear, they’re not casual wear and you can even wear it with a formal morning coat ensemble, you can wear it to a wedding, or to just a board meeting. So if you don’t have a Winchester shirt in your wardrobe yet, I suggest you invest in one. Start out maybe with a solid color such as light blue and later on, you can advance to stripes, maybe checks, or other things.
12. Open Weave Cloth Dress Shirts
Most shirts in the market today come in a medium heavy weave that is quite tight, however, during the summer, an open weave shirt is much more pleasant to wear because it allows a lot more air to your skin. That way, you’re less prone to sweating, you stay cooler, and you are just more comfortable. The problem is most over the rack shirts do not offer those fabrics and even a lot of custom makers don’t offer those fabrics. So if you go to Italy, in the areas where it’s quite warm, all the bespoke shirt makers will have those fabrics because they know how comfortable they can be and they’re just a godsend.
Personally, I have a range of different open weave dress shirts and sometimes they’re so open that my chest hair pokes through so they are not meant for a super formal board meeting but that aside, they’re extremely comfortable in all kinds of summer situations where you want to stay as cool as possible. Pair that with a fresco jacket or other open weave suiting fabrics and you stay a lot cooler than in a regular suit with a regular dress shirt.
13. Pin Collar Shirts
In the 90s, when power suits were popular, a lot of people would wear tab collars and pin collars. In recent years, they’ve fallen somewhat out of favor but it’s a great way to add a different accessory to your outfit that elevates your tie knot and makes you look a little more debonair. So what is a pin collared shirt? Pin collared shirts are essential for collar bars because with those, you can just pin a hole into your shirt collar.
If you have a safety collar pin, you can in theory, just punch a hole into any kind of shirt collar and while that works, I suggest to get a pin collar shirt because you can use it with a bar you can even use it with a clip and particularly with a safety pin, it always looks good . It just looks sophisticated and different from what other people wear yet it’s not a very loud and ostentatious.
If you want to buy a pin collared shirt, I suggest you get a custom shirt; even online custom shirtmakers offer them today. It’s just important to place the hole at the right height and ideally, you want it very close to the edge of the shirt collar, otherwise, you can’t wear it with certain items such as a safety pin and it usually looks best when it’s kind of in the middle of the collar vertically, that way, you just get the nice look and you still have enough space for your tie knot and overall, you create a harmonious outfit that is quite unique.