First 10 Dress Shirts a Man Should Own

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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.

Plain white dress shirt - simple and neat
Plain white dress shirt – simple and neat

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.

Placket comparison
Placket comparison
Bow Tie in Soft Ancient Madder Silk with Red Macclesfield Neats Micropattern

Fort Belvedere

Bow Tie in Soft Ancient Madder Silk with Red Macclesfield Neats Micropattern

A photo of a Blue Cornflower Boutonniere Buttonhole Flower Silk

Fort Belvedere

Blue Cornflower Boutonniere Buttonhole Flower Silk

Burgundy Silk Pocket Square with little Paisley Motifs

Fort Belvedere

Burgundy Silk Pocket Square with little Paisley Motifs

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.

Fancy weave dress shirt in white
Fancy weave dress shirt in white
Madder Silk Tie in Bottle Green Macclesfield Neats Blue Orange Pattern - Fort Belvedere

Fort Belvedere

Madder Silk Tie in Bottle Green Macclesfield Neats Blue Orange Pattern

Silk Pocket Square in Brown with Blue, Green, Red Large Paisley Pattern- Fort Belvedere

Fort Belvedere

Silk Pocket Square in Brown with Blue, Green, Red Large Paisley Pattern

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.

subtle waffle pattern
subtle waffle pattern
If you do not fancy the waffle pattern, you can go with a herringbone pattern
If you do not fancy the waffle pattern, you can go with a herringbone pattern

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.

A selection of light blue dress shirts in different shades
A selection of light blue dress shirts in different shades

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.

You can also opt for a twill weave
You can also opt for a twill weave

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.

An ivory shirt works well for brown toned jackets
An ivory shirt works well for brown toned jackets
Houndstooth Silk Bourette Bow Tie Burgundy Cream - Fort Belvedere

Fort Belvedere

Houndstooth Silk Bourette Bow Tie Burgundy Cream

Edelweiss Boutonniere on a white background

Fort Belvedere

Edelweiss Boutonniere Buttonhole

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.

Light blue stripes on a white background
Light blue stripes on a white background

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.

A few of Sven Raphael's striped dress shirts
A few of Sven Raphael’s striped dress shirts

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.

Black, blue, and white checked dress shirt
Black, blue, and white checked dress shirt

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.

A beautiful OCBD by Turnbull and Asser
A beautiful OCBD by Turnbull and Asser

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.

A denim shirt can look great if combined properly
A denim shirt can look great if combined properly [Image Credit: Pinterest]

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.

Outfit Rundown

I am wearing a classic white fancy weave shirt with a small waffle pattern. It has a shirt placket with French cuffs and a medium spread collar as well as the mother of pearl buttons. My cufflinks are gold monkey-fist cufflinks. They are very timeless and classic and if you invest in your first 10 dress shirts this would be the cufflink I would wear with it because you can always wear it. If there was one other pair, I would get one in silver because you can really wear it for very formal evening events or not so formal board meetings or even to the office. It’s just a cufflink that you will never regret having bought. My jacket is green and it’s part of a suit. It’s single-breasted, it’s a slightly heavier fabric with a really nice color depth. I combined it with a dark green madder silk tie. There’s enough contrast there especially because of the white shirt and I combined it with a pocket square that picks up the green tones and just ties it all together.

Sven wearing a green jacket, brown houndstooth pants, white shirt and Fort Belvedere accessories.
Sven wearing a green jacket, brown houndstooth pants, a white shirt, and Fort Belvedere accessories.
Madder Silk Tie in Bottle Green Macclesfield Neats Blue Orange Pattern - Fort Belvedere

Fort Belvedere

Madder Silk Tie in Bottle Green Macclesfield Neats Blue Orange Pattern

Silk Pocket Square in Brown with Blue, Green, Red Large Paisley Pattern- Fort Belvedere

Fort Belvedere

Silk Pocket Square in Brown with Blue, Green, Red Large Paisley Pattern

Mid Brown and Green Shadow Stripe Ribbed Socks Fil d'Ecosse Cotton

Fort Belvedere

Mid Brown and Green Shadow Stripe Ribbed Socks Fil d'Ecosse Cotton

Monkey Fist Knot Cufflinks - Vermeil Sterling Silver Yellow Gold Plated

Fort Belvedere

Monkey Fist Knot Cufflinks – Vermeil Sterling Silver Yellow Gold Plated

My slacks are also part of a suit. They’re kind of brown and off-white houndstooth flannel and they contrast well the texture of my jacket but because the colors are all so soft and warm, it all works together. My shoes are dark green suede tassel loafers that pick up the brown tones of my pants as well as the green tones of my jacket and tie thus tying it all together. The socks I’m wearing are brown and green shadow stripe socks, picking up the brown tones and green tones once again thus creating a harmonious outfit.

Do you have all these dress shirts in your closet? If not, what are your dress shirt essentials?

Reader Comments

  1. Blue chambray, if properly pressed, also adds interesting variety to a wardrobe. Certainly not needed on a top ten list, I admit.

  2. You’ve expressed your preference for “classics”… reaching back to an age when men dressed with greater care, perhaps. I’ve noticed the shirts worn in your videos tend to be unpressed and their collars seem curled. Is that intentional? Why?

    Your videos and articles are the best on the internet regarding sartorial history and construction techniques. I have enjoyed every single one of them.

    Sartorially yours,
    Herbert Carlock

  3. Always associated the checked dress shirt with casual, never dress shirts. Personally, never saw a suited individual wearing one, although with odd jacket combos yes, of course. To me, I would uncheck this shirt as a dress shirt, but de gustibus non disputandum est and all that sort of thing.

    1. I agree, and I’d add the denim shirt to that. I don’t have a problem with this American, informal style (as the owner of a beloved pair of mid-thigh Western leather boots, and several denim shirts), but it is not (and never will be) formal. I have more of a problem with check shirts, whether in a formal or informal setting, however. They just make you look like a geek or a chav in my opinion, but as you so wisely say, to each their own…

  4. Not a bad article and video. However, stay clear of the spread and semi-spread collars. Mr. Raphael…you should be too sophisticated for that…the spread and semi-spread collars are simply inappropriate. In addition , please be more scrupulous in your use or English grammar and sentence construction in our language.

    1. Spread and semi-spread collars are in no way inappropriate for everybody – it’s dependent on the shape of your face. A button-down collar that might look great on a pencilneck with a round or square face looks ridiculous on those of us with oval or diamond-shaped faces and neck sizes bigger than 16″. Being sophisticated entails selecting the best choice to enhance your specific build and look, not simply following arbitrary rules that are defined according to averages that exclude most.

    2. I concur with David V. about avoiding the spread and semi-spread collars, especially the wide-spread collars which I see as affectations. Also, avoid the really short button-down collars that some designers seem to think are hip these days. Even Lands End has shortened the length of its collar points, and the ones they now sell look silly when worn with a tie. Stick to a straight collar for dressy occasions, and an OCBD when you want a more casual look and you’ll be fine. as for grammar and sentence structure in English, I’ll cut Raphael some slack since English is his second language.

  5. Bengal stripe is not mentioned, although some of the blue shirts pictured appear to be Bengal stripe. Still an excellent and informative article.

    1. We mentioned striped, doesn’t have to be a bengal stripe as that is too bold for some.

    1. End on end is nice, I have them and I do have a linen shirt, but they are not my first 10 must have shirts. Of course, everyone is different in their needs and preferences.

  6. Dear Mr. Schneider and readers of the Gentleman’s Gazette,

    Could you please help me with a few questions I have? I did not mean to post these questions
    in response to an article that does not directly relate to them, but this way currently appears
    ideal for attracting help about the matter.

    The questions relate to general wardrobe care. I have never had an issue with moths because
    I always take great care of my wardrobe and keep everything perfectly clean, but I would like
    to employ some means of moth infestation prevention. I was just reading the Gentleman’s Gazette
    article titled “How To Store Clothes” from 2011, and Mr. Schneider wrote there that adding a little
    bottle of cedar oil to the closet can be used to achieve infestation prevention. Could somebody
    please give me a few more details on how to use a cedar oil bottle for this purpose? I currently
    have four questions in mind:

    1. Is it sufficient to merely remove the lid of the cedar oil bottle and to put the bottle inside the
    closet, or do I also need to do anything else? This question sounds elementary, but I would
    rather be safe than sorry.

    2. Could somebody please recommend cedar oil products that would be ideal for this situation?
    It would be highly appreciated if the products are available on Amazon.

    3. Is one bottle of cedar oil enough regardless of the closet’s size?

    4. Will it ever be necessary to replace the cedar oil or maintain it in any way?

    I will welcome any information you can provide on the matter, as well as any advice you may
    have on what steps I can take from here.

    On a note to Mr. Schneider, thank you very much for this article. This article and the recent
    article on underrated and overrated dress shirts have greatly helped shape my understanding
    of how an elegant and classic dress shirt should look.

    I thank you all for your time, and I wish you a pleasant day.

    Yours sincerely,
    William L.

  7. Great article! The only thing that I don’t agree with is the soft washed denim shirt. It’s not for everyone and it can’t be dressed up. Instead, I would say to get a pastel shirt of your favorite color, for example a pastel green, pink or orange. A shirt of these colors can be both casual and formal and it’s always good to wear your favorite color.

    Best regards

  8. To me, a properly cut shirt is very important, however, if i have to spend top dollars, I raher do it for a superb linen shirt, rather than a formal cotton shirt that spends its life undre a jacket.

    My prefrence goes to Giovanni Inglese, who cuts the most fantastic linen white shirts I have even seen: one does need to a small mortgage, but those shirts are the best money can buy.

  9. Everyone has their own formulas on what to wear. I stay away from white shirts as they make me look washed out. Pale colours and stripes work welll for me.

    Great article!

  10. I love the plethora of white and off white shirts. They go with anything at anytime. I tend to buy shirts with the thinking that I will only wear them on their own and then they never work with my suits and ties well. The white shirt is definitely a staple. Thanks for the video. Very insightful!

  11. None of these are ‘dress’ shirts as we in Egland understand the term. They are merely everyday shirts of no consequence. Perhaps in America, where standards are lower, they might pass muster but not here, I assure you.

  12. My favorite white shirts must be suitable for tuxedo wear several times per month. As the first six of a shirt collection that fills a rolling store rack, they have a rib pattern and french cuffs with a medium collar and plastic point reinforcement. To be sure I have one ready for travel, I have one unopened. They do double duty with my banker’s suits. I also have pleated tux shirts for really black tie affairs. For summer wear, my sherbet colors w/out pocket are loved by the ladies combined with an off-white linen vest for my KEYone cell phone/organizer by Blackberry and fountain pen. As an Architect, for years the corporate daily dress was a black on white stripe (6 per inch) shirt, midnight blue blazer and stone khakis. Grey slacks were the local option as a ‘Cape Cod tuxedo.’ The plain white or black or college stripe tie went into the pocket when on Nantucket, except for a funeral. For Christmas, buy me a light blue oxford button-down shirt. So versatile and classic. Again, thanks for the quick refresher on shirts. Geoff

  13. These First 10 dress shirt idea are no doubt the most usefull and their concept are really useful in day to day life. Thank you so much for sharing this article. Keep up the good work.

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