How To Dress Like a Gentleman: 10 Modern Style Guidelines to Follow

Style is subjective. But every well-dressed man is governed by a set of fashion principles, whether he knows it or not. That’s what makes a wardrobe work. And it’s what makes a man look polished, no matter what he’s wearing.

To learn how to dress like a true gentleman, you’ll need to develop your own set of style guidelines. Need a good place to start? Check out ours!

How to Dress Like a Gentleman in 10 Steps

1. Make fit your number one priority.

It really doesn’t matter what you’re wearing. A guy can look great in sweat pants and a T-shirt if those items fit his body perfectly. A good fit means your garments look the way the designer intended them to appear. Nothing is baggy, bulging, or loose. But nothing is pulling or straining either. This can only be achieved through eagle eye precision when purchasing clothes—and a ruthlessness when cutting items that don’t work. When it comes to fit, a gentleman is bent on achieving nothing less than perfection.  

2. Insist on good quality materials and construction.

Most men solve the quality problem by shopping at stores that are higher-priced. But just because a shirt costs five times more, that doesn’t mean it’s been made from better material. Nearly every shopping mall clothing brand includes items that are cheaply made from low-quality materials, regardless of how expensive they are.

The best way to ensure you’re getting amazing quality is to select the fabric yourself and have your clothes made custom—but you can also develop a tailor’s eye for items you buy off the rack. By building a wardrobe of items that pass the high-quality bar, you’ll give off a far more polished look (and your clothes will last much longer).

3. Get at least one perfect suit.

Every man needs that ideal workhorse suit. It’s good for job interviews, date nights, friends’ weddings, and that big presentation at work. And while you might be able to get away with a sub-par fit and questionable quality in a casual outfit, these points matter most when it comes to getting the perfect suit. We believe every man deserves a custom-fitted suit in a fabric and cut that suits his style. If you’re curious about getting a perfect suit for yourself, we know where to look.

4. Celebrate your style quirks.

Regardless of what Instagram conditions all of us to believe, each of us has a truly unique sense of style. Take a second to dig deep and identify a few of your own personal style quirks. You might really love floral print skinny ties. You might have a love affair with that beat up vintage bomber jacket. You might go for loud socks, unique timepieces, or a signature sneaker. Whatever it is, find your quirk and celebrate it! And forget about what classic men’s fashion rules say.

5. Always know the dress code.

Obviously, we’re not fans of strict fashion rules. But every gentleman knows to ask about the dress code before going to an event. And we all need to understand the difference between casual, business casual, semi-formal, and black tie. These guidelines are rarely set in stone—but knowing the rules will give you confidence as you choose outfits for special occasions. And eventually, with some practice, you’ll develop a knack for pushing the limits of these dress codes in a way that makes your creative style stand out.

6. Experiment with footwear.

Menswear is made up of highly subtle variations on the same classic theme—shirt, pants, jacket, shoes. But footwear is the one area in which we have room to play. If your shoe collection consists of one or two pairs of dress shoes and a trusty pair of sneakers, it’s time to branch out a bit. Try pairing an understated pair of Chelsea boots with your suit. Or a bright salmon boat shoe with your Chino pants. Good shoes make a good look.

7. When in doubt, choose a timeless look.

We encourage you to take risks. We want you to celebrate your personality through clothing. But we all know that kind of innovation takes energy and effort. Every now and then, it’s good to stick to classic looks that you can pull off with instant success.

Think a charcoal suit, white dress shirt, solid tie—always a good combo for the boardroom. Or consider a stunning yet classic black tuxedo for your wedding. Traditional looks don’t have to be boring. And when they’re perfectly executed with the ideal fit, you’ll end up looking perfectly timeless.

8. Curate your own set of style icons.

Style inspiration is the best way for a gentleman to make sure he’s dressing better over time. Take stock of fashion’s best, from both past and present, and choose a few men whose fashion sense you really admire. Some of our favorite style icons from this past year, in no particular order, are Jeff Goldblum, Roger Federer, Eddie Redmayne, and David Beckham. But classics like Cary Grant, James Dean, and Steve McQueen also deserve your consideration. Regardless of who you choose, collect visual evidence of looks you like and emulate some of the ideas with pieces you already own.   

9. Identify the best clothing maker for your style.

It’s always good to have a go-to, never-fail choice for when you need to purchase a new item of clothing. Whether that means you find all your best pieces at Saks or you’re in a dedicated relationship with your favorite custom tailor, identify this partner and stick with them. The next time you need a new winter overcoat or a tailored dress shirt, you’ll know exactly where to go. And by purchasing a majority of your items from the same retailer, it’s easy to have a cohesive look to your entire wardrobe.

10. Take calculated risks.

If you want to be known for your fashion sense, you need to start making waves with your everyday clothing choices. These don’t have to be over-the-top. But make sure you’re taking small fashion risks every now and then to keep things interesting. Wear that pointy-toed pair of camel brogues. Rock a bold striped dress shirt at a business meeting. Go sans-tie with a draped scarf for one of your business casual days. Some of these experiments will flop from time to time, but you might discover something truly interesting by pushing outside your comfort zone.

If you’re looking to add a perfect suit to your wardrobe, or to partner with a clothier who can help you revamp your entire look, visit a Knot Standard showroom in your area. When you make an appointment with us, you’ll meet with your own personal style advisor. They’ll help you create a custom garment (or wardrobe) from the ground up. Learn how to dress like a gentleman by following the ten guidelines above—and infusing your wardrobe with custom menswear from Knot Standard.