Business Shirt

April 20, 2024

Sharpen Your Style: The Ultimate Guide to Choosing the Perfect Business Shirt

Picture this: you’re preparing for an important meeting, a presentation that could impact your career trajectory. The weight of decisions, the thrill of leadership—you’re ready to take your career to the next level. But conquering the boardroom goes beyond just strategy and expertise. It’s about projecting an image of unwavering confidence, authority, and success. And that’s where the perfect business shirt steps in. Choosing the perfect business shirt can feel like a constant battle. But fret no more! This guide equips you with the knowledge and confidence to select a shirt that not only fits flawlessly but also elevates your professional look.

A well-chosen business shirt transcends mere clothing; it’s a silent communicator. It broadcasts an air of competence, organisation, and attention to detail—all qualities that inspire trust and respect in a professional setting. Studies from Harvard Business School even suggest that the colour of your shirt can influence how you’re perceived. A crisp blue button-down, for instance, can project a sense of trustworthiness, perfect for that crucial interview.

This ultimate guide empowers you to curate a business shirt wardrobe that speaks volumes about your professionalism and style.

Fit is King: The Foundation of a Polished Look

Fit is paramount. A baggy shirt drowns your physique, while a tight one restricts movement and creates an unflattering silhouette. The key is to achieve a clean, polished look that flatters your body type. Here’s how to find your perfect fit:

  • Know your measurements: Understanding your neck size, sleeve length, and chest and body fit is crucial. If you’re unsure, consider using a measuring tape at home or visiting a tailor for professional guidance
  • Embrace the benefits of a tailored fit: Tailored shirts take your look to the next level. They ensure the shirt drapes seamlessly around your body, creating a sharp and sophisticated silhouette. While not always necessary, a tailored shirt can significantly elevate your wardrobe.

Fabric Fundamentals: Comfort Meets Style

The fabric you choose impacts both comfort and style. Here are some popular options for business shirts:

Cotton: The undisputed champion, cotton offers breathability and a classic look. Opt for Egyptian cotton for a luxurious feel and superior wrinkle resistance.

Poplin: A versatile choice, poplin combines the comfort of cotton with a smooth, wrinkle-resistant finish.

Linen: Ideal for warmer climates, linen offers exceptional breathability but wrinkles easily. Consider a linen blend for a balance of comfort and wrinkle resistance.

Blends: Blends of cotton and synthetic fibres like polyester offer a balance of comfort, wrinkle resistance, and affordability.

Collar Confidence: The Perfect Frame for Your Face, Like Choosing the Right Cheese for Your Wine

Choosing the right collar style for your business shirt is like selecting the perfect cheese to complement your favourite wine. Both elements play a crucial role in enhancing the overall experience. A well-chosen collar can frame your face and elevate your look, just like the right cheese can elevate a glass of wine. Here’s a breakdown of some popular collar options, helping you find the perfect match:

Spread collar: This versatile option is like a creamy brie – it flatters most face shapes. The wider collar points spread outwards, balancing a rounder face and creating a sense of sharpness.

Button-down collar: Offering a more casual look, the button-down collar is akin to a mild cheddar. Ideal for relaxed office environments, it adds a touch of approachability, similar to how cheddar’s familiar flavour creates a sense of comfort.

Wingtip collar: A formal choice, the wingtip collar is like a sharp vintage Gouda. Its pointed collar tips fold outwards, creating a distinct V-shape. This adds a touch of sophistication, perfect for special occasions or paired with a tie, similar to how a vintage Gouda’s complex flavour profile complements a fine wine.

Cutaway collar: Imagine a semi-hard Gruyere cheese, with its slightly curved edges. The cutaway collar shares this subtle curve, offering a more contemporary and streamlined look compared to the classic spread collar. It works well with both rounder and more angular faces.

The Finishing Touches: Details that Make a Difference, Like the Perfect Garnish on a Masterpiece

The finer details of your business shirt, like the finishing touches on a masterfully plated dish, can elevate your look from good to great. Here are some aspects to consider, ensuring your professional presentation is as meticulously crafted as a culinary masterpiece:

Cuffs: Choose between single cuffs (the most common), double cuffs (worn with cufflinks for a formal look), or rounded cuffs (a more casual option). Imagine these as the garnishes on your plate. Single cuffs offer a clean, minimalist finish, like a simple sprig of fresh herbs. Double cuffs with cufflinks add a touch of elegance, similar to a decorative edible flower. Rounded cuffs provide a relaxed touch, akin to a sprinkle of colourful chopped nuts.

Button placement: A hidden placket offers a clean, minimalist look, ideal for a formal setting. This is like a beautifully smooth sauce base on your plate, allowing the main ingredients to shine. An exposed placket adds a touch of detail, similar to a delicate drizzle of sauce across the dish.

Buttons: While seemingly a minor detail, the quality and style of your buttons can make a difference. Opt for buttons made from durable materials like mother-of-pearl or resin. Avoid overly flashy or plastic buttons, as they can detract from the overall look. Think of them as the finishing touches on your artwork; high-quality materials create a more polished and professional impression.

Pocket or no pocket? This depends on the formality of the occasion and your personal style. A shirt with a breast pocket offers a touch of practicality, similar to having a side dish to complement your main course. However, for a more formal setting, a cleaner look might be preferable, akin to a beautifully plated single course meal.


Choosing the perfect business shirt is an art form, and with the knowledge you’ve gleaned from this guide, you’re well on your way to becoming a master. Remember, a well-chosen shirt isn’t just an article of clothing; it’s a silent testament to your professionalism, confidence, and attention to detail.

At Winslow Style, we’ve been crafting high-quality business shirts for over 15 years. We understand the importance of fit, fabric, and style, and we’re passionate about helping you find the perfect shirt to elevate your professional presence.

Imagine yourself walking into a meeting, sharp and confident, in a shirt that perfectly complements your physique and personality. That’s the Winslow Style difference.

Ready to experience the confidence that comes with a perfectly tailored shirt? We’re confident you’ll find the perfect shirt to help you conquer your next business challenge.


Dress shirt sizes typically involve two measurements: neck size and sleeve length. You'll find these measurements denoted as a number and slash (e.g., 15/32), with the first number being your neck size in inches and the second being your sleeve length. Some retailers may also include chest size for a more comprehensive fit guide. If you're unsure about your measurements, consider using a measuring tape at home or visiting a tailor for professional assistance.

A well-fitting dress shirt should hug your body comfortably without restricting movement. The shoulders should sit flush without bunching, and the sleeves should reach your wrist bone with the first button of your jacket fastened. The shirt shouldn't gape at the chest or waist, and the collar should comfortably rest around your neck without feeling constricting.

Cotton is the most common fabric for business shirts, offering breathability and a classic look. Opt for Egyptian cotton for a luxurious feel and superior wrinkle resistance. Poplin is another popular choice, combining comfort with a smooth, wrinkle-resistant finish. Linen is ideal for warmer climates but wrinkles easily. Blends of cotton and synthetic fibres offer a balance of comfort, wrinkle resistance, and affordability.

The presence of a pocket on a business shirt depends on personal preference and the level of formality. A shirt with a breast pocket offers a touch of practicality, but for very formal settings, a cleaner look without a pocket might be preferred.

While many retailers offer off-the-rack business shirts, consider investing in a tailored shirt for a truly customised fit. Tailored shirts ensure the garment drapes seamlessly around your body, creating a sharper and more sophisticated look. Some retailers may also offer made-to-measure options, allowing you to select specific fabrics, colours, and details to create a truly unique shirt.