Dress shirts are one of the most important style basics in your wardrobe and most men have dress shirts but often, they don’t quite work with the rest of their wardrobe and so over the years, I have had hundreds of dress shirts and I learned a thing or two, so if I would have to do it all over again, these are the first dress shirts I would start with.
While dress shirts form the foundation of a classic man’s wardrobe, they’re often overlooked in favor of suits, shoes, or accessories, however, if you get your first dress shirts wrong, it’s much harder to combine them with other things and you may not get the wear out of them. With these dress shirts, you’ll basically be equipped for all classic men’s style outfits yet you really cover just the basics so you don’t spend more money than you ultimately have to. Basically, there are always three main considerations; color, fabric, and shirt details.
1. Plain Weave White Solid Dress Shirt
I suggest going with a medium spread collar, as well as barrel cuffs because it allows you to wear it in more formal and less formal settings. It’s also something you can pair with jeans or denim, as well as with a very formal business suit. Opt for a medium weight fabric because it’s something you can wear year-round. If it’s too thin, it’s just appropriate for summer. If it’s too thick, you can only wear it during the colder months of the year and overall, you want something that’s as versatile as possible when you’re just starting out.
Personally, I’m a big fan of cufflinks and for that, you need a double cuff or a French cuff, however, I suggest not to opt for those in your very first shirt because it’s an additional expense and you’re just starting out, you’re better off investing money in your first shirt.
For a traditional placket, I suggest you get a French style which means there’s no additional piece of fabric; it is sewn underneath the buttons, it’s just a very neat seam. On top of that, I suggest you skip the pocket simply because a shirt pocket is really not meant to be used. That being said, a lot of off-the-rack shirts come with shirt pockets. I have a few shirts in my wardrobe that I got vintage or used that have shirt pockets but if I go custom and I have the option, I always skip the pocket.
2. Fancy Weave White Dress Shirt
Preferably with double cuffs or French cuffs. A shirt with a subtle waffle pattern weave makes it slightly different compared to a plain weave in the sense that if you look at it very closely and the light shines in a certain direction, you can see it has a pattern, however, from a few feet away or a few meters away, you think it’s a solid shirt with a nice depth of color. Again, skip the pocket and if you went with a French placket before, go with a shirt placket around this time simply so you have a range of different things in your wardrobe.
It just creates a more symmetrical look especially when you wear a bow tie. If you wear a necktie, it doesn’t matter because your shirt placket is covered up anyway. If you don’t want a waffle weave, a very popular pattern is a small herringbone pattern weave. Look for a very fine weave because that’s something that will stand the test of time. Again, for the collar, I would go with a classic medium spread collar because it suits every face shape, it works with tie knots, bow ties, or as an open collar.
3. Light Blue Dress Shirt
It should be made of a medium fabric, ideally, plain weave. Again, barrel cuffs, no pocket and French placket. If I say light blue, you’ll encounter probably 500 different shades of light blue and what you choose is ultimately up to you and your taste. I find a lighter shade of light blue that is more pastel in color is more versatile, especially in the beginning.
4. Another Shade Of Light Blue
You can go darker, you can go lighter, just make sure it’s different. For the fabric itself, I suggest getting something in a twill weave because it’s a new small weave pattern that you don’t already have and it’s a very classic thing, it is hard wearing, and it’s particularly good in a slightly heavier fabric for winter because you want to have a variety of shirts in your wardrobe. Of course, if you live in a place where it’s always cold, you should get shirts that are heavier.
If you live in a tropical climate, only get shirts that are lighter in weight. I’ll suggest going with double cuffs and if you want to experiment with a collar here, you can do so. Maybe you get a slightly larger collar, not a small collar, and make sure overall, it’s just something that works out well for you. If your other light blue shirt has barrel cuffs or button cuffs, opt for a French cuff just to give you more versatility.
5. Ivory Dress Shirt
It should be distinctly different from white if you hold them next to each other, however, it’s so close to white on its own that most people would never realize you’re not wearing a plain white dress shirt. Plain white works really best with dark colors; it could be a dark green, dark blue, dark charcoal, or black, however, when you pair it with warmer colors such as brown, all of a sudden, the white just looks wrong.
It’s especially true if you pair a white dress shirt with tweed, the contrast is too stark and it doesn’t work as well. This is when the ivory shirt really shines, it’s super versatile because you can wear it with a business suit in charcoal or a navy but you can also wear it with much warmer tones or summer suits and it will always look more appropriate than the plain white shirt.
In terms of details, the choice here is really up to you. If you wear more cufflinks, go with a French cuff. If you don’t have cufflinks, go with a barrel cuff. If you already got the basics covered, the ivory shirt is just a shirt that I would bring when I travel and because of that, I would probably get it in a barrel cuff because that would allow me to wear it with more casual outfits, as well as formal business suits.
6. Blue Striped Shirt On A White Background
The size of the blue stripe is up to you. I’d stay away from extremely fine ones or extremely bold ones, go with something in the middle down the line because that will work well with all kinds of solid suits. It adds another pattern and you can then either go with a solid tie or have a patterned tie as well. Something that works particularly well are small Macclesfield neats micropatterns.
7. White Striped Shirt On A Blue Background
Ideally, the stripe should be different from what you already had so I’d suggest going more with a finer stripe rather than with a bolder stripe because you want it to be super versatile. Again, a finer stripe will look more like a solid from afar but it will add a different color depth; it works well from close-up because even if you have a pattern, let’s say a stripe and a tie, the stripe is so fine that it works really well together.
8. Checked Dress Shirt
It can either be a light blue check on a white background or you can maybe go with a red and blue check on a white background. It just adds an additional color to your shirt wardrobe plus red and blue are staples in a classic man’s wardrobe so you’ll always be able to wear it, it never looks out of place, and it’ll look good with a blazer. If you wear it more casually, again, go with a button-down collar because it works well with checked shirts. I would also opt for the button cuffs because you will likely be wearing this kind of shirt more in a casual environment.
9. Oxford Cloth Button Down Shirt
It’s an American staple, it’s a very hard-wearing cloth. I’ll get it in a light blue color because the Oxford fabric has strands of different colors in white and blue so it gives a nice color effect in the light but you can also wear it with or without a suit when you work. It’s just a shirt that will stay in your wardrobe for a long time.
10. Soft Washed Denim Dress Shirt
Ten-fifteen years ago, it wasn’t really something that men would actually wear. In recent years, it has become so popular that men stock loads of them. In general, a soft washed denim dress shirt really tones down any kind of formal garment you have. So if you are only in a white-collar environment, it may not be the ideal thing for work but it’s definitely something you could off work. You can always tone down your suits or basically any kind of outfit with this kind of soft washed denim shirt. I know one could argue that is a fairly recent invention and it may not stand the test of time and while you were right about that, with the general casualization of men’s wardrobe, I’m pretty sure it’ll still be around in 10 years, we’ll see.