Have you ever wondered how many dress shirts you must have to have a complete classic style wardrobe?

If you’re a follower of the Gentleman’s Gazette, you may have come across the guides about 10 dress shirts every man should invest in but if you’re looking into building a timeless classic man’s wardrobe, ten is just the start.

To answer the question right from the get-go, how many dress shirts do you need? The answer is it depends. Let’s break it down. Personally, I have about 60 to 70 dress shirts; sometimes I add, some sometimes I’ll retire some, but overall, that’s the number. Personally, I don’t consider it to be too much for a number of reasons.

A selection of dress shirts

1. Dress Shirts Are The Backbone Of My Wardrobe.

I hardly ever wear undershirts and so it’s always something that protects my jackets and my outer garments from my body fluids. With the exception of going to the gym or maybe mowing the lawn, I usually wear dress shirts or maybe a polo shirt when it’s really hot and I’m in a very casual setting. So for me, a dress shirt is truly an everyday piece of my attire.

A few of Sven Raphael’s striped dress shirts

2. Dress Shirts Come In Endless Variations.

Yes, you may have one white shirt but then there are different weaves, weights, patterns, collar shapes, cuff shapes, fits, and so it’s not difficult for me to always come up with a new shirt that’s different than any other that I’ve had so far.

Striped green and white dress shirt with micropattern tie from Fort Belvedere

3. Dress Shirts Provide Personality.

I actively try to incorporate different colors into my overall outfits. So rather than going with that white shirt, I maybe go with an off-white or a light pale yellow.

A blue dress shirt with a purple paisley tie from Fort Belvedere

4. Dress Shirts Are An Investment.

I still have shirts in my wardrobe that are more than ten years old and I still have them in my rotation. Of course, the more shirts you have, the fewer you wear the individual ones, the longer they will overall last.

The oldest shirts I have in my wardrobe today I bought used from a gentleman who was a realtor and about to retire, he had my height and he had all of his shirts made at Siniscalchi in Milano and it’s a bespoke shirt maker that is very expensive. Shirts usually go for around five to six hundred euros and he was just handing them to me at bargain prices and they all had very cool fabrics, very unusual styles. It’s not something I would suggest you invest in when you’re just building a shirt wardrobe but it’s definitely something you can add once you have all the basics covered. If you take care of your shirts properly, they should last you a long time.

Siniscalchi in Milano bespoke dress shirt

If you have shirts made for you, it may be a good idea to invest in separate collars and cuffs because that’s what usually wears out the first and so you can just exchange that and still enjoy that shirt. Now, some of the old Siniscalchi shirts I have are just starting to fray around the edges on the collar and the cuffs and since I do not have any excess fabric, I could turn them into Winchester shirts meaning I use contrasting white collars and cuffs, that way, I could still enjoy wearing the overall shirt without having to just buy an entirely new shirt.

Francesco Barberis Canonico

The other option would be to simply wear them as they are and for example, Francesco Barberis Canonico is someone who could afford a new shirt but he deliberately chooses to wear really worn down shirts and if you take a closer look, you can always see that his shirts are heavily frayed and you can see the interlining and white sometimes popping out from underneath but just like having all the rugs in your home with signs of wear, it’s kind of a very British attitude and he just goes with it and it suits his style. I’m not saying this is something that you should practice and it requires a certain style in order to pull it off. More often than not, people would probably think of you as frumpy or not well taken care of if you have a meticulous wardrobe with fraying shirts.

5. I Like To Change My Shirt Wardrobe With The Seasons.

In the winter, I wear heavier oxfords or heavier twill shirts, sometimes they have a little flannel texture, just so I’m warmer and more comfortable. In the summer, I wear very lightweight fabrics with an open weave that help my skin to breathe and keep me cooler.

Open weave shirt fabric, ideal for summer

Of course, during the in-between seasons, you can wear medium weight fabrics and ultimately, you have to analyze where you live. If you live in a climate like I do where you have very hot summers and very cold winters, you need different shirts than if you live let’s say in Sri Lanka where it’s hot all year round.

Dry cleaning shirts is unnecessary

6. I Am Not A Big Fan Of Dry Cleaning Dress Shirts.

Yes, it would be easier to do so but I have very good quality dress shirts and at a dry cleaner, they usually wash them not as gently and carefully as it can be done at home. Also, they’re usually not completely hand ironed but machine ironed and all of those things help to wear down your shirt prematurely.  

How Many Shirts Should You Invest In When You’re Starting Out & You’re Interested In A Classic Wardrobe?

I would say ten is the bare minimum.

The Basics

I think every man should invest in ten dress shirts if they have somewhat of a use for dress shirts on a regular basis. If you wear shirts to the office, ten is actually the bare minimum. I suggest having more like a three or four-week rotation which means 15 or 20 dress shirts. Of course, the bigger the rotation, the longer your shirts will last.

For the most part, the first ten shirts should be mostly white, off-white, or shades of blues.  Personally, I’m a big fan of pastel-colored shirts, light greens, or lavender, or yellow, but typically that’s something you should add on top of the ten basics.

A white French cuff dress shirt with mother of pearl buttons

If you don’t have to wear a dress shirt to work and you don’t like wearing dress shirts, I suggest you have at least three dress shirts that you can always rely on. One is a white dress shirt, ideally with French cuffs for cufflinks without a chest pocket and it’s something that you can wear for anything from a job interview, to a funeral, to a wedding, or any kind of other formal events.

If you don’t have cufflinks or you don’t want to invest money in them, go with a single barrel cuff which is also known as a button cuff. If you want to invest in cufflinks, I would suggest you get one pair in gold and one pair in silver in a very traditional style without any diamonds or colored stones. Personally, I would choose a monkey fist knot cufflink because they’re versatile, they’re classic, and it’s something you could wear with any kind of outfit.

Checked Shirt Fabric – Ideal for Business Casual

Checked Shirts

Ideally, you get it with a button-down collar because it’s more casual and you don’t need to wear it with any form of neckwear and for that, you definitely want to have barrel cuffs or button cuffs and you can also have a chest pocket if you want.

Linen Jacket and denim shirt

Denim Shirts

It can really help to dress down other things, you don’t have to iron it, it’s something that is popular right now, and has been popular for the last few years. It’s soft, it’s hard wearing, and it’s something that works well in any wardrobe.  

The Sky Is The Limit For Menswear Enthusiasts

Obviously, that’s me! You can have just ten shirts that are all in white but they can have different cuff styles, collar styles, weaves, front plackets, buttons, and all those little details make the shirts different and suited for different occasions.

Butler Luxury Hanger in Whiskey

Of course, at this point, storage can be a challenge and basically, you can fold them and put them in drawers but I find that it takes up a lot of drawers and so I hang all of my shirts on specific shirt hangers that are not too wide so they don’t take up too much space in my wardrobe. Personally, I use the ones from Butler luxury which served me quite well.

A green suit combined with a pastel-colored dress shirt with an orange shantung bow tie and boutonniere from Fort Belvedere

So once you have all the basics covered, I suggest you go with pastel colors. Pastel pink, pastel lavender, green, you can have other shades that are combining those colors and just play with things. You can also add different kinds of patterns such as maybe a small houndstooth shirt, a horizontal striped shirt, or stripes in an unusual color.

Experiment With Different Shirt Details

Of course, you can also experiment with different fabrics and different weights, as well as finishes and on top of that, playing with a collar shape is probably the detail that has the biggest impact because it defines the V shapes and the triangles that lead to your face.

Play With The Different Options You Have

First of all, it’s the height of your collar, then the spread of your collar, also how long you want the collar to be in the front, as well as how much tie space you want which really depends on what kind of tie knots you tie. If you have bigger tie knots such as the Windsor, you want more tie space, otherwise, you can get away with no tie space at all. Of course, you can also have club collars or create collars for collar pins with little pin holes in them just so you have exactly the right shirt for the right occasion.

Wearing a collar pin is something you should consider if you want the classic look

I also urge you to experiment with pleats in the back or if you have little grinze patterns, you can have shirts that have a higher degree of handwork, you can have shirts with different buttons, you can experiment with shirts from different shirt makers. Over time, you probably create some preferences for certain kinds of shirts for certain occasions and it’s just a joy to experiment and try new things.

Black Bow Tie and Cummerbund in Black Faille Grosgrain

If you attend evening events regularly, you also may want to invest in different kinds of evening shirts. Some could have wide pleated fronts or slim pleated fronts. You could have different kinds of Marcella inserts, you can have starched shirts, and it’s just interesting and with black tie, there’s not a whole lot variety in what you can do so changing up the shirt detail has a much bigger impact than it would on let’s say a business suit.

CONCLUSION

Overall, just like with anything else in your wardrobe, it really depends on your needs and what you want, however, once you know what you’re going for, it pays to start out with the basics that give you the most use for your purpose which means the lowest cost per wear.

In general, that means staying away from super flashy or unusual things and it means that you leave them behind even though they may be really discounted on a super sale because even if you get the shirt at 90% off, it is kind of wasted if you just wear it twice in a period of 10 years.

Gentleman’s Gazette

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