If you’ve ever been on X (formerly Twitter), there’s a good chance you’ve come across Derek the Menswear Guy (@dieworkwear). He’s known for providing practical style tips for men that just make sense, and his threads always end up becoming viral.
If 2025 is the year you want to level up your style, here are 15 essential tips from X’s most celebrated menswear expert.
Tailor, Tailor, Tailor!
Everything rises and falls on tailoring. It’s easy to fall into the trap of buying the first suit you try and calling it a day, however, proper tailoring can make all the difference. Here’s three basic rules you need to follow:
First, make sure the jacket collar sits flat against your neck without gaps. Second, check that nothing pulls, puckers, or bunches when you move. And thirdly, don’t go for too slim a fit—most suit issues come from a fit that’s too tight. Nail these three basic rules, and your suit will always like it was made just for you.
Think of Clothes as a Social Language
Instead of just following every Tiktok trend, consider utilizing the clothes you wear as a social language to build your personal style. This means studying the history of a garment and finding meaning in it.
For example, skinny jeans with black boots and a black leather jacket might be considered out of trend, but it references history. Whether it’s punk and post-punk in the 70s and 80s or rock and roll in the 50s, this outfit is a symbol of cultural resistance and non-confirmity, and it already says so much about you and what you value.
Attend Funerals in Black Tie
A black suit and tie might seem overly formal for a funeral, but it shows a high level of respect for the deceased and those they left behind. Funerals don’t always have dress codes, so if you’re at a loss for what to wear, a black suit and tie combo is always an old faithful.
Look at the Collar First
When checking if a suit fits well, start with the jacket collar. It should sit neatly against the back of your neck without lifting or gaping, even as you turn your head or move your shoulders. If there’s a gap or it shifts around, the fit is off no matter how good the rest of the suit looks. A collar that hugs the neck smoothly is a key sign of good tailoring. It shows the jacket has been properly shaped to the user’s frame.
The Right Leather Shoes Can Be Comfortable
Did you know that for generations, men wore leather soles for long walks and even sports? It may sound bizarre in the age of
Go to a store that sells quality shoes. Research which stores in your area have been existing for decades and creating their own shoes from scratch; probably one that’s family-owned and operated. It might be a pretty penny, but a good pair of leather shoes is still a good investment in the long run.
Use Your Best-Fitting Clothes as the Standard
Are you having a hard time figuring out sizing? Go into your closet and grab the clothes that fit you the best—your sharpest button-up, most comfortable sweater, favorite pair of tailored pants, and go-to jeans. Place each item flat on a firm surface like a table or the floor. Then, using a soft measuring tape, take detailed measurements of each garment. This will give you a clear picture of the dimensions that work best for your body. Having these numbers on hand is incredibly helpful when shopping or getting clothes tailored; it takes the guesswork out of fit and helps ensure every piece you buy feels just right from the start.
Fit and Silhouette Are Two Different Things
Fit refers to how a garment sits on your body. For example, whether the collar rests cleanly against your neck or if there’s any pulling or wrinkling. Many people assume tighter is better, but most common tailoring issues—like gaps at the collar, puckered lapels, tight buttons, pants gripping the thighs—are caused by clothing that’s simply too snug.
Once you’ve figured out your proper fit, only then you can focus on silhouette. Silhouette is the overall shape your outfit creates when you ignore all the finer details. It’s the visual impression your clothes make from a distance, defining your outfit’s structure and style.
Invest in Quality Basic Shirts
Basic shirts include a good flannel, a button-up linen, and yes, even your good ‘ol basic tee. Casualwear is indeed diverse and even contextual depending on your culture, location, and the weather of that location, but if you love workwear, Americana, or Westernwear, basic tees are a necessity.
Steam is Bad for Tailored Suits
Heat and pressure are used in tailoring to shape fabric, helping it keep the structure over time. However, steam relaxes those shapes by softening the fibers, causing them to lose their form. That’s why too much steam can undo careful tailoring work, especially in garments designed to keep their structure.
Luxury Brands Are Just Labels
If you’re into fashion, you’ve probably noticed the rise of luxury brands stamping their labels onto streetwear. Gucci, Balenciaga, Louis Vuitton—name the house, and it’s probably made its way to casualwear. These items may seem aspirational, but remember these are just labels and they don’t necessarily speak to quality. Luxury brands do this to create artificial scarcity, and it doesn’t mean you’re paying for your money’s worth just because your shirt has the Comme des Garçons logo on it.
You Can Wear Suit Jackets with Jeans
Here’s how: Through a tailored jacket that looks like a sport coat. You can do this by option for a jacket that’s made of material like tweed, which evokes the vibe of casual, country, and sporty. Avoid using regular suit jackets, which look more like they’re suited for a business meeting.
Build a “Springboard Wardrobe”
Derek is not a big believer in capsule wardrobes, as he believes everyone has different needs and styles. Instead, he encourages men to build a “springboard wardrobe,” which is designed to help them figure out their own taste.
This springboard wardrobe can include tan chinos or blue jeans, a navy sport coat, gray wool trousers, Oxford cloth button down, Shetland sweaters, a gray sweatshirt, three pairs of shoes (loafers, work boots, and
Hem Your Trousers
Have you ever seen trousers that look incredibly ill-fitting on the wearer? The culprit is usually unhemmed bottoms. When they bunch up over the feet, it can make outfits look unkempt and just off, regardless of how well everything else is styled. Always consider how the legs of your pants are falling down, and hem if necessary. If you don’t have time for hemming, always grab a belt or suspenders to take in the waist.
People Who Run Warm Can Still Wear Layers
So you think layers add interest to an outfit, but you’re someone whose body runs a little warm, or you live in a hotter climate. In this case, consider opting for reverse layering, which is wearing something like a tank top below a retro-styled knit or shirt, then adding accessories like sunglasses or a statement necklace. Another option is learning how garment construction works, and which materials and fabrics allow for better breathability.
Style Isn’t Exclusive to “Fit” People
And lastly, Derek reminds his audience that looking and being stylish isn’t exclusive to “fit” people. Being fit doesn’t automatically translate to an ability to wear anything and still look good.
As an example, Canadian chef Matty Matheson isn’t considered a gymbro by any means, but he’s still widely celebrated by menswear-dom for his style. This is because he’s learned to see fashion as a social language and how to choose pieces that fit his body type. Once you get these down pat, you’ll also look stylish and clean regardless of your body type.
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