A well-chosen shirt is one of the most versatile items a man can own. Whether you’re heading to work, a weekend brunch, or a night out, the right shirt can elevate your look in an instant. But knowing how to style it for different occasions is key to looking sharp and feeling comfortable.
Let’s explore how to style men’s shirts for both work and play—showing you how to balance smart, professional looks with casual, laid-back styles. Let’s dive in!
Work Shirts: Dressing for Success
Workwear is all about making a good impression while staying comfortable throughout the day. The key to a successful work shirt is choosing one that fits well, feels good, and complements your professional environment. Here’s how to style your shirts for work:
The Classic Button-Down Shirt
A classic button-down shirt is the backbone of any office wardrobe. It’s smart, clean, and polished—ideal for interviews, meetings, or casual Fridays.
• Styling Tip: Pair a crisp, well-fitted button-down shirt with a suit or blazer for a formal business look. Choose neutral colours like white, light blue, or pale grey for a timeless vibe, or experiment with subtle patterns like checks or stripes to add a bit of personality.
• Fit: A slim fit is usually the best choice for most body types. Avoid shirts that are too baggy or too tight, as they can look unprofessional. A well-tailored shirt creates a streamlined silhouette and ensures you look polished. You can shop for high quality shirts from Wolf in Sheep’s Clothing.
The Polo Shirt: Smart-Casual Workwear
On less formal days or during smart-casual work environments, a polo shirt can be an excellent alternative to a button-down. It provides a refined yet relaxed look, perfect for casual Fridays or a day at the office without a big meeting.
• Styling Tip: Pair a high-quality, well-fitting polo with chinos or dress trousers. Keep the look neat and understated by avoiding overly bright colours or bold patterns. Stick to classic colours like navy, grey, or white for maximum versatility.
• Fit: A slim-fit polo with a slightly tapered waistline offers a modern, flattering look. Make sure it fits comfortably around the shoulders and chest but isn’t too tight.
Play Shirts: Casual Looks for Every Occasion
When the workday is done, your shirt can transition from formal to casual in a heartbeat. Whether you’re heading to the pub, going for a weekend brunch, or just hanging out with friends, the right shirt can help you look stylish without much effort.
The Casual Button-Down Shirt
The casual button-down shirt is a fantastic option for relaxed outings. Whether it’s a lightweight cotton shirt for summer or a flannel shirt for cooler months, this style is a great way to look put-together while still being comfortable. According to King Size, there are so many use cases for a casual shirt, so it's always nice to have a few quality pieces to choose from.
• Styling Tip: Tuck your shirt into chinos or dark jeans for a semi-smart look, or leave it untucked for a more laid-back vibe. Add a stylish jacket or a pair of loafers to finish the look if you're heading somewhere with a slightly more elevated atmosphere.
• Fit: Opt for a regular or slim fit, depending on your body type. Avoid oversized shirts that can look sloppy, and instead focus on shirts that fit well across the shoulders and chest, with a bit of room around the waist.
The Short-Sleeve Shirt: A Warm-Weather Essential
During warmer months, a short-sleeve shirt is a go-to for staying cool and looking sharp. A short-sleeve button-down or a smart polo is perfect for casual days spent outdoors.
• Styling Tip: For a clean, relaxed look, pair a short-sleeve button-down with tailored shorts or lightweight trousers. If you’re aiming for a more casual approach, pair it with denim jeans or chinos. Make sure the shirt is well-fitted, not too baggy or too tight.
• Fit: A slim or tailored fit works best for a neat and stylish appearance. Steer clear of overly loose or boxy designs, as these can detract from your overall look.
Comments You Want to See About a Clothing Brand
Do you want to get more adventurous and purchase items of clothing from a new brand? Perhaps you’ve always stuck to the same names.
But, you’re not ready for a change. This can be a good way to experiment with your style, as well as enjoy wearing better materials.
Just know that you should research the brand carefully when you’re shopping online to ensure you get what you want. It can help to read customer reviews before spending your money. Here are some comments you’ll want to see.
Using Quality Materials
When you’re willing to spend a lot of money on a clothing brand, you want to ensure that you’re getting quality goods in return.
Something that you should look out for in the reviews is comments on the quality of the materials. You want to ensure that customers are happy with how they appear, feel and wash. Then, you can know that you’re spending your money in the right place.
Offering Various Styles
You want to be able to explore various styles and gain confidence from your outfits. Therefore, you want customers to be impressed by the styles on offer. Check the reviews to see whether this is a versatile clothing brand that’s constantly offering its customers something new. Then, you can know that it’s worth exploring the online store regularly.
Delivering Quickly
Do you have a special event coming up and you need to make sure that the clothing arrives in time? Take a look at reviews to learn from other customers’ experiences. They’re going to let you know what the shipping is like and if their order was processed quickly.
If you see that a lot of people have encountered delays, this can be a red flag.
Conclusion
Styling men’s shirts for both work and play doesn’t have to be complicated. By choosing the right fit, fabric, and pairing options, you can create looks that are versatile, comfortable, and stylish.
Whether you're heading to the office, meeting friends for lunch, or heading out for an evening of fun, your shirt can help you make a lasting impression. With these tips, you’ll be ready to master the art of shirt styling for any occasion—work or play!
Jenny Kakoudakis likes to blog about travel. She launched award-winning Seasons in Colour in 2014 and the luxury interior design blog All The Pretty Homes in 2024. When she is not chasing criminals out of the financial system (her day job), she gets planning her next adventure abroad.