Classic, timeless, simple, yet with endless variations in color, design, collar, buttoms, cuff, length and more. I’m talking about the button-up collared shirt.

Often it is the classic white button-up we hear about, but let’s be honest, we don’t always want a white shirt, and white may not even be our hue, and we may not want cotton! We may want silk, linen, seersucker or a blend. In other words, the options are a plenty. And on top of that, we want it to fit our body and our lifestyle. So where do we begin? That is what we will talk about today, to simplify the process, so you can home in on what you uniquely are shopping for and find it with more success and ease.

But first!

How did you do on your task from Part Trois/Three? Have a look below as a reminder:

Part Trois Wardrobe Task

Examine the sweaters you do have in your closet. Honestly assess how they are holding up, how often you wear them, and how you feel when you do wear them. Then, make a list of 2-3 sweaters you would like to make sure you have in your closet. Do you have these? If not, start to peruse brands and styles that speak to you. No matter their price point, put them on your KarmaNow list of favorites so that when/if they go on sale, you can check whether the new price works in your budget. Either way, you have begun to clarify what you love and what would work for your everyday life. When we purchase a quality sweater, we can prevent having to shop for it again, so keep in mind the Cost-per-Wear concept to ease your mind. 

And if you are new to our series, be sure to read Part Une/One as it details the full approach which is an approximately 12-month long wardrobe project, buying one (sometimes two) items each month, adhering to our list that we have created of about 12-15 items.

Now to Part Quatre!

Today, we’re going to dive deep into how to determine the best size for each of us, when purchasing a bespoke shirt is the best idea, discover brands to shop, share 23 ideas for how to style, and I’ll also share a brand I am loving and recommending. Let’s get started!

Part Quatre: Button-Up Shirts, Getting the Right Size

Button-up/Button-down shirts are a staple to have in our closet year-round. The fabric type may change, but the style is dependable as night and day. This type of shirt is a classic for a reason – it can be worn many different ways, for different occasions and during different chapters in our life.

Where to begin — Know Your Measurements

First, begin by knowing yourself, specifically, literally knowing your body’s measurements. More than anything else, when you have these details, the sizing of any brand won’t matter, as each will be different. As we talked about in Part Deux during our discussion about denim jeans, measurements will render the best results as they are universal; sizing designations by each brand are not.

Take measurements with a measuring tape for the following:

• Shoulder width: from the edge of one shoulder to the other. When measuring, remember to relax your shoulders or have some measure for you as shrugging them will reduce the length.
• Arm length: From the end of the shoulder where the arm begins to hang, to just below the wrist bone. Make sure when measuring your arm is hanging naturally.
• Bust: measure loosely around the center part of your chest (all the way around – front and back)
• Center Back length: from the spinal vertebrae that is found along your shoulder-line all the way down your back to the length you prefer.
  • sometimes called Torso: LilySilk’s definition — “Tilt your head forward and feel for the bony bump where the slope of your shoulders meets your neck. This is your 7th cervical (or C7) vertebra—and the top of your torso length. Measure from this top to the waist, that is your torso length.”
• Waist: around your waist at its narrowest point
• Neck (sometimes, but usually only for men’s shirts)

Once you have all of these measurements, you then adapt them to the type of fit you want. If you want classic, your measurements will be similar to the shirt’s measurements, but if you want a more fitted or oversized, the lengths will change. But knowing your personal measurements ensures you purchase a shirt that will fit you and also tells you if you need to order a custom size, with the measurements ready to do so with ease.

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Types of Styles to Consider

Long-sleeve or short-sleeve button-down

• Oxford style: made of cotton with a classic, tailored design, crisp, often with mother-of-pearl buttons
• Linen: worn primarily during warmer months, but has a similar classic style. Breathable, yet protects the skin from the sun.
• Silk: offers a more fluid look, but can be tailored, as well as oversized. A nice layering option underneath suit jackets and blazers. Naturally keeps the body warm, but also cool in different settings as the skin can breathe
• Oversized/Boyfriend shirt: the shoulder measurements will be longer to drop over the edge of the shoulder, and other measurements will also be larger by design. Can be made in various natural materials
• Chambray/Denim shirt: made of cotton yet more sturdy as it is denim, they are more casual, and offer a versatile option in the wardrobe for pairing with a wide-range of colors
• Cropped shirt: no need for tucking in, this shirt will often have a classic design, but simply have a square hem and sit at around the waist.
• Satin: similar to a silk shirt, often used in work or formal settings. Due to its the movement of the fabric, it works well under suits and blazers, but also look sharp on its own paired with pants or a shirt.
• Seersucker: made with 100% cotton and is a breathable, lightweight fabric, often worn during warmer months when we want to keep cool. The seersucker effect and thus texture is created by “weaving tight and loose threads, allowing the fabric to sit away from the skin, enhancing airflow in hot weather.”
• Poplin: naturally wrinkle-resistant, this 100% cotton weave, while plain, is unique as it is made “with very fine horizontal ‘ribs’ that results in a strong, crisp fabric with a silky, lustrous surface.” Chosen for a classic look with a touch of casual. It doesn’t stain as easily, and also more easily releases odors when washed than other fabrics.
• Plaid design: Sometimes called checked or flannel design, but made with cotton, sometimes silk.
• Stripes: There are many different types of stripes. Here are the most common in women’s shirting: pinstripe, hairline (very thin and running close together), pencil stripe (a bit wider than pinstripe), ticking stripe (resembling a mattress’s ticking, often has a bit of texure), candy stripe (thick, bold stripe, even, much like you would see at a sweet shop), butcher’s stripe (uneven – thicker and then thinner, and on a larger scale), and there are more! View all of them here and learn about each one.

As you look through the above list, look at the various seasons you need shirts for – winter, summer, the shoulder seasons of spring and autumn. Which styles would work well in multiple seasons? Which ones would be perfect for work and layering with other pieces? Choose your preferred styles to fit your preference and lifestyle, and then below, I will share with you a list of brands that offer particular types of designs so that you can narrow down where you shop.

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23 Styling Ideas for Wearing a Button-Down/Up Shirt

1. A white shirt with black pants or denim – simple, dependable

2. Layer over a fine turtleneck, leaving the buttons undone to the navel. Potentially layer with a tweed blazer.

3. Layer over a tank, camisole or scoop-necked tee, and leave undone.

4. Wear a cropped shirt, naturally, it will be untucked, wear with a high-waist midi-skirt (see here)

5. Wear under suiting or a blazer

6. Wear a chambray shirt with denim jeans, then layer over the top an oversized blazer with a complementary color for your skin tone (see here)

7. Candy stripe shirt (silk or cotton) with dark denim jeans for a dressed up look on a casual day. Oversized of either would work well also (see here)

8. If leaving untucked, make sure the hem bottom isn’t too long. It should hit at no longer than mid-hip, maybe an inch or too longer for the oversized effect.

9. Tie/Knot the front hems. This works best with an oversized shirt and quickly gives your figure an hourglass shape.

10. Wear a silk shirt in the same hue as your trousers for a monochromatic look. Choose wool trousers for a slight differentiation in the textures of the two separates. Keep shoes the same hue as well or similar. Let the accessories do the talking – handbags, jewelry, even a scarf and sunglasses (see here)

11. Leave untucked, especially a white cotton shirt, and wrap with a belt. This works well when wearing skirts, stylish shorts, but trousers too (see here)

12. Wear underneath a sweater or sweater vest, and leave the shirt untucked. Commonly described as a preppy look, this works well for giving layers of warmth while having style. Wear with jeans or trousers.

13. Dark-hued shirt and a skirt for evening attire. Very CBK (Carolyn Bessette-Kennedy-esque), as it’s casual, while dressing up, maybe even wearing heels. (see here)

14. A linen long-sleeve shirt with shorts for summer comfort and sun coverage (slather the sunscreen on the gams)

15. An oversized shirt (silk), tucked in, with dress shorts to provided a balance of proportions.

16. Oversized, untucked, bottom half unbottoned for movement, worn with a favorite pair of jeans. A casual, yet stylish look (see here).

17. A Oxford button-up with oversized trousers and chic accessories (handbag, sunnies, belt, bracelet, etc.) (see here)

18. With wide-leg jeans, pointed toe pumps or boots, left untucked or with a French tuck, and add a belt. (see here)

19. With a slip/slim midi-skirt, white or preferred cotton tank and left un-buttoned. Or similarly, wear a midi body-con dress, and wear the shirt over the top, let loose or tie at the waist. Pair with flat sandals.

20. Cropped palazzo or wide-leg jeans and a cropped shirt, long or short sleeves with boots, sandals, or sneakers. Also, if high-waisted, a classic shirt tucked in with a great belt. (see here and here)

21. Chambray shirt and white jeans. (see here)

22. Cropped straight leg pant or jeans with classic button-up. (see here)

23. A classic white Oxford or oversized, paired with straight-leg jeans and black or brown classic accessories. (see here)

Common Issues and How to Avoid Them

1.Gaping

This will often happen if we have the wrong size. Everything else may fit fine, but our bust measurements are too tight. Either size up or order a custom size. However, sometimes, no matter what the size, a gap will appear between the buttons at our bust-line, and in fact, The Shirt company is known for their patented design that offers an interior button that keeps that gap shut. Having a couple of their shirts, I can attest, they work!

Other options include using double-sided tape specifically designed for fabric. Try Fearless Tape, Flash Tape, Fashion Tape, or, if in a pinch, safety pins (which is often what I reach for and have on hand just in case a button pops off).

2. Keeping white shirts white, and ironing and laundering properly each shirt

If our shirt is white and cotton, then we can launder it ourselves, but do let it air-dry and then steam to iron. Choosing not to put it in the dryer will prevent yellowing. And the best way to iron both cotton and silk, as well as linen (if you want to get rid of the wrinkles) is a steamer. I have had mine for over 15 years ( in 2012 – see the exact one below – Jiffy Steamer), and it still works great and ensures I protect my delicate fabrics.

When it comes to cleaning my shirts, I often take my button-ups (cotton and silk) to my dry cleaner as the cost is minimal, especially for the cotton shirts, as I get the men’s shirt price.

3. Armpit stains

The good news is that it is preventable and it isn’t because we are perspiring excessively. It actually has to do with a daily hygiene product we likely are using. The Wirecutter explains:

“Those unsightly yellow stains on your white tees are not evidence of poor hygiene or excessive perspiration. They’re the result of a chemical reaction that occurs when aluminum—an active ingredient in antiperspirants—combines with the proteins in underarm sweat. The simplest way to avoid this is to swap out your antiperspirant for an aluminum-free deodorant (which controls odor but not perspiration), or to go au naturel. But if that switch doesn’t appeal to you, fear not: You have plenty of other options.” Read their full article for laundering solutions.

You can use armpit shields, a sweat-proof undershirt, and always remember to wash promptly or take it to the dry-cleaner swiftly so the sweat doesn’t linger and make it more difficult to remove. Often, sweat in silk shirts isn’t visible until it sits for a while, so speedy cleaning will make a difference. Read The Guardian‘s article for more ideas.

4. Sheer or partially sheer shirts

Sheer isn’t a problem if you love the fabric and it is the look for you, but even if a shirt is sheer, wearing matching skin-tone undergarments will make the shirt appear less sheer. Of course, you may want what is worn beneath to be seen as part of your style, and that, too, is a reason to purchase sheer. An interesting style detail of note. If you are wearing a white sheer shirt, and you want it to appear less so, wear a nude bra, but then wear a white camisole, rather than a nude cami. It will look more streamlined than you may expect.

Sometimes we cannot know how sheer a shirt when we are purchasing online, so make sure you have the option of returning or exchanging it. Case in point, as I share below, one of the silk shirts I purchased, but not the others, was too sheer for what I was looking for. So I promptly returned it and received a refund.

The Button-Ups I Added to My Wardrobe During this Project

Over the past few decades, I have gone through my fair share of cotton Oxford shirts. None of them was bespoke, and because of my long arms and broad shoulders, not one has ever fit me well. So what would I do? You guessed it. Rolled the sleeves up or flipped the cuff, so that it looked intentional for the sleeve to hit mid-lower arm. This bothered me, as I at least wanted the option of having my sleeves at full length.

So during this project, I told myself to find a few button-down shirts, and if you can, have them customized to my measurements. Enter Lilysilk. I like to wear my shirts under a blazer as the blazer can act as a coat, or stay on if the weather becomes cool, which it often does here in Bend, as we have chilly mornings and evenings, even in the summer. So I have opted for silk with a matte finish and opaque.

The prices are quite nice with Lilysilk, ranging from $130 to $225 depending on the style and color you choose. And the best part, and why I chose them for this project for what I needed is that they have a custom option. For an additional $30, you can have the shirt you choose made to measure. It only took an additional two weeks, and within that window from when I purchased it, it was at my door.

Even better, during the customization process, they reached out to confirm certain details and have me remeasure just to make sure. “Were my shoulder measurements correct?” Yep, I have broad shoulders. You will see in the tag of the one shirt I have customized, that the label says as much. Not that that matters, but if I ever need to re-order this shirt, I will know that it has the measurements that fit me to a T. Also, the measurements are saved in my Account with the company.

The other two shirts I ordered were ‘oversized’ by design, so I didn’t need to customize these. Both are medium – actually, all three are, and based on the detailed measurements they share, I knew they would fit my arms and shoulders well, and they do. I did end up returning one of their shirts because it was too sheer, and the refund was quickly returned to my account, which I actually used to purchase the white silk shirt you see here. For less than $500, I have three new shirts, and they all fit my body. I couldn’t be more pleased.

You will see me wearing the pinstripe shirt in April’s A Cuppa Moments. All of the shirts pair well with navy trousers or jeans of light or dark washes. I have worn blazers over them, and due to their light weight, there is no bulk, and the comfort with two layers is ideal compared to what it would be with a cotton Oxford shirt. So, for my style preference – blazers frequently worn, these silk shirts work perfectly.

Shop each of the shirts below:

Brands to Shop (and the styles they offer)

The brands are many. Depending upon your preference, style, and budget, the brands you gravitate to will be unique to you; however, having tried and purchased many classic Oxford shirts as well as silk shirts over the years, there are brands that are worth noting and that I trust.

If you are seeking a bespoke/custom option, our budget will determine where we shop. As I shared above, the customization from Lilysilk was very nominal, $30, so well worth it to get exactly what I needed. Some bespoke shirts can cost $400-$800, as Jo Ellison detailed in this recent post in The Financial Times, but again, well worth it, as it fit her to a T.

Below are brands to explore as well as what typical style components they are known for:

Budget, yet quality options:

• Boden
  • affordable, with a wide range of styles, cotton, and linen.
  • Many different styles and fits, solid colors and stripe options. Silk in different weights, and custom sizing is available for $30 additionally to the price of the shirt.
• J.Crew
  • Classic, oversized, stripes, available in cotton and at very low prices.
• Quince
  • Classic button-downs, cropped, cotton, linen and silk shirts available.
• Everlane
  • Classic Oxford styles, silk as well as linen.

Mid-luxury

• Alex Mill
  • Lots of linen at the moment, but oodles of classic cotton and poplin in modern styles as well as classic designs.
• Brooks Brothers
  • Classic Oxford shirts, various colors, designs, and fits. They also have linen and cropped shirts. Made to Measure is available for shirts, suiting separates and other items.
• Comme Si
  • Their La Shirt Classica is priced just under $300 and come highly recommended from Vogue for classic, yet modern in its design. Available in a variety of different colors, fabrics and even stripes.
• MM LaFleur
  • cotton, silk, poplin, many different styles, necklines and lengths
• Lilysilk
  • Quality silk in different weights and finishes, solid and stripe styles in different fits. Customization is available for $30 on top of the price of the shirt.
• Polo Ralph Lauren
  • Cotton, silk and linen. Classic Oxford styles with a wide range of colors and stripes. Chambray too.
• The Shirt
  • Known for their patented ‘No Gap’ buttons (one, sometimes two buttons are placed on the inside of the shirt to ensure there is no gap down the middle of the shirt)
  • I have a couple of their short-sleeve Perfect Shirts, and love the slight bit of flexibility for movement and cuffed sleeves.
  • Non-iron
  • Find all sorts of styles, colors. Their Oxford style shirt, cotton with some stretch.
  • Their Jet Set Icon shirt, non-iron, is the classic white shirt that they have become known for.
• Sold Out NYC
• ~Their The Everything shirt has been recommended by Vogue and is an oversized Oxford style available in classic colors of white, blue, and stripes, as well as other neutral hues.
• With Nothing Underneath
  • This British brand offers cotton and linen in a variety of styles, colors and stripes

Luxury

• Budd, London
  • The place spotlighted in Jo Ellison’s piece in The Financial Times for bespoke shirts.
• Ralph Lauren
  • Classic Oxford styles in cotton, linen and silk.
• Sarah Alexandra
  • Beautiful, classic Italian cotton shirts in a variety of different styles, colors, solids and stripes.
• Toteme
  • A Swedish brand offering casual, yet comfortable and chic styles. Classic styles available as well.
• TWP (Trish Wescoat Pound)
  • Modern and classic designs. Oodles of cropped options, and linen, as well as cotton, chambray and even organza and paper leather.
• Rubirosa Paris
  • If in Paris, be sure to visit this new shop, as it is full of colorful button-down shirts. Read the article (gift link for NYTimes) here.

Again, this is just a sampling of the brands, but these are brands to explore for oodles of options. Most brands will offer one or a few button-down shirts in each collection, but if you want to know the exact measurements of a particular style a brand has become known for, these brands help you feel confident in your purchase that what you choose will fit you well. Please do share brands you have shopped and love that offer worthwhile button-down shirt options.

The series continues!

The series, How to Build a Wardrobe to Love and Live In Every Day, continues with Part Cinq/Five next month on Tuesday, May 12th. 

Between now and then, take your measurements. Then, determine which style/design of button-down shirts you feel most comfortable in and that you need in your wardrobe to provide more options with what you already have or will be adding during this 12-month wardrobe project. Peruse the brands above to determine which brands speak to you, and even save the ones you would love to invite into your closet. Do this no matter their price point. Put the ones you have chosen on your KarmaNow list of favorites so that when/if they go on sale, you can check whether the new price works in your budget. Either way, you have begun to clarify what you love and what would work for your everyday life. And keep in mind, when it comes to button-up shirts, when you find what you love and fits you well, it is a great idea to buy multiples of that exactly item as they are separates that get mixed and matched with so many different pieces, and often are not the star of the outfit, but are necessary to complete a polished ensemble.

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