Updated by Wesley Kang
Most people hate having to follow rules. But very often, rules are there for a good reason. For example, rules on how to dress well work. Obviously, every person will have different rules on what dressing well entails as that is different for everyone. What works for one person may not work for another person. For example, depending on whether you're a W9 vs W2 worker, you may have different dress codes at work.
But despite the variance, there are some general rules that apply to most men. Otherwise, things like advice and general trends wouldn’t exist. No doubt that men can learn a lot by listening to the advice of others.
It is important to keep in mind that they are just guidelines and not something you have to stick to no matter what. Learn more in our article about how to dress like a man, and collect the right wardrobe essentials with our article on things every man should own.
As men’s fashion becomes more notable and talked about there are new trends and new fall-back positions that are considered the ‘default.’ There are also several other rules that you may or may not have encountered before.
So we decided to put together this ultimate list of some of the most important dress and clothing tips for guys. These rules have stood the test of time and have been proven to be helpful in most situations.
22 Rules for How to Dress Better | Men’s Style
1. Wear Clothes That Fit Properly
One of the biggest mistakes men make when dressing is that they pick clothes that are too large. Oversized shorts and pants that are too long will make you look unkempt and unprofessional. Most of these problems can be solved by just picking smaller clothes that flatter your figure more.
Clothing that follows the natural lines and angles of your body is a good idea. To get a better fit on your formal clothes, take them to a tailor so they can customize their fit. We also recommend that you check out our fit guide.
Baggy clothes not only are uncomfortable, but they also make you look younger and less distinguished. Nobody wants to go out with someone who dresses like they are still 12 years old.
2. Incorporate Classic Styles like Simple Patterns
Patterns are a double-edged sword. They can be very interesting to look at and provide a good contrast with solid colors, but they can also be too loud and distracting. In general, we would recommend staying away from extremely bright patterns and complex designs on dress shirts.
If you do wear patterns, make sure that they revolve around 2-3 basic, softer colors like a light blue shirt that go well together. That does not mean a complex pattern is always bad; in fact, it can be a good addition, such as a tie with a unique pattern to accent a solid suit. Our advice is to stick to one patterned piece of clothing per outfit. Nimble Made has a great collection of patterned dress shirts that are great for everyday wear and a variety of dress codes.
3. Embrace the Slim Fit
Slim fit pants don’t mean you have to be very slim to wear them, it just means the leg has a specific design and trim to it. Slim fit or straight leg pants look good on pretty much any guy, tall or short, and can go with a ton of different shirts, jackets, etc. If you are muscular, go for the best athletic fit dress shirt to go with your pants.
4. Incorporate Different Shoe Styles
We have seen guys combine dress pants with athletic sneakers or wear sneakers with a pair of khakis. We get that a lot of men choose shoes for comfort rather than style, but after a certain point, it’s just ridiculous.
Shoes are an important part of the outfit and pull the look together. That doesn’t mean you always have to wear really fancy dress shoes, just shoes that actually match the outfit and occasion.
For example, don’t wear your running shoes with your slim-fit pants. Instead, get some casual canvas sneakers with a solid coloring. Chukka boots and driving mocs are other good, versatile shoes that can be worn with several outfits. Make sure to have a pair of high quality loafers or dress shoes around for more semi-formal occasions.
5. Explore Your Personal Style
Spend some time looking up different brands and styles, picking out which ones you think would look good on you. If you have friends and feel comfortable doing so, let them give you some advice on what to wear. Start building a capsule wardrobe to interchange your items of clothing for max versatility.
6. Get the Basics to Build an Entire Outfit
One thing you need to do is build up your basic wardrobe fundamentals. That means getting a reliable assortment of pants, shirts, button-ups or button-downs, etc. that can match well with anything.
It is a good idea to start building this base with neutral colors like greys, blacks, whites, navy, and browns/tans. These colors are all very neutral and easy to match with basically any other colors. The point of these clothes is to serve as a base to which you can add and modify other outfits to get the specific look that you want.
Other wardrobe ‘staples’ include a belt, plain shoes, socks, maybe a watch or two. You can think of these wardrobe staples like raw ingredients in the kitchen: with a bit of practice, you will know how to mix and combine them whatever way that you want.
7. Layering for Different Seasons
Layering is a good way to get the most out of your wardrobe and will teach you how to create interesting outfits using everything that you have, especially during the fall and winter. For example, spread collar dress shirts and pullovers are great for layering and give you more ways to combine outfits.
Also, layering is useful when you are not sure how hot or cold a place will be. An extra layer might keep you warm when it's cold out while you can take off a layer if you end up getting too hot. Incorporate a quality leather jacket for the extra cold events in the winter.
Dress shirts which feel like tailor-made will look great on you once you remove one or two extra layers. Just make sure you don’t put on so many layers that you cannot move comfortably.
8. Don’t Worry About Trends
Trends, like the seasons, come and go and sometimes return. When you are trying to revamp your wardrobe, try not to bother yourself much with what is ‘trendy’ or what all your favorite models and celebrities are wearing. Instead, focus on finding a style that matches you, then worry about trends and fashion later.
Part of knowing how to dress well is first developing an eye that can catch good clothing decisions no matter what trend happens to be in style at the moment. Besides, developing your own unique style allows for more creative expression and lets you experiment more with outfits, color schemes, etc.
You will be much more comfortable and confident if you develop your own clothing fingerprint instead of just copying what you see in the magazine.
9. Get Rid of Graphics T Shirts and Logos
Graphics and logos can be fun but very often they are just distracting and take away from the overall design of your outfit. Besides, colorful shirts with patterns, images, and slogans are considered immature and will consequently make you seem younger and less mature.
So one of the best ways to seem more mature with your dress is to stay away from shirts and pants that have bright logos, prints, and slogans on the front. That doesn’t mean that you can never wear a bright-colored T-shirt with your favorite sitcom quote on it, just that those kinds of shirts should not form the basis of your entire wardrobe.
Keeping a simpler, more understated base to your wardrobe will make you look more mature and put together.
10. Beware Bright Colors
Bright colors are dangerous to play with. When used correctly, a strategically placed pink or bright blue can add a lot of depth and accent to an outfit. Too much color and you can just look like a Jackson Pollock gone wrong. So all other things being equal, your wardrobe should favor more neutral, earthy tones like browns, grays, blacks, dark blues, and whites.
Obviously, you can put some color in your outfits but just make sure that they are balanced with these more neutral colors. The good thing about grey or khaki pants is that they can go with most other colors. You should also avoid combining multiple bright colors, even if they technically are complementary colors, like green and red or orange and blue.
We recommend sticking to a single color accent per outfit. Other brighter but mostly neutral colors that work well include navy, green, blues, and soft pastels like yellow or pink.
11. Invest in Higher Quality Clothes
You do not need 20 pairs of pants and 30 shirts to make a good casual wardrobe. You can get away with a very diverse range of outfits with only about 5 pairs of pants and maybe 10-15 types of shirts.
The idea is to go for quality clothing over the quantity of clothing. Clothing that is well made will last you a long time and will ultimately be more comfortable to wear than cheap clothing that is mass-produced. Focus on high quality materials like 100% cotton and sustainable practices.
The trick is finding good quality clothes that can mix and match with one another, instead of having a t shirt and pants designated for one outfit only. As you train your fashion eye, you will get better at picking out clothing matches and combinations.
12. Get a Clothing Iron
We see this problem a lot; men wearing wrinkled shirts that look like they’ve been wadded up in their closets for months. Every man should invest in a good clothes iron (or steam presser) to make sure their outfits are looking sharp and clean.
Wearing wrinkled shirts not only increases the risk of damage but all the lumps and creases can completely ruin how the clothes compliment your figure. Invest in a solid clothes iron and ironing board; trust us, you will not regret it.
And yes, you should make sure that you iron both the inside and outside of your clothes. Turn your shirts inside and outside to make sure you get all the wrinkles with the iron. A full guide on how to iron a dress shirt here.
13. Get a Solid Pair of Denim Jeans
Everybody needs a good pair of jeans, men included. Jeans are some of the most versatile pants and can be used in casual and more formal settings. When it comes to jeans, we recommend that every guy have at least one pair of authentic, genuine denim jeans.
You see, a lot of jeans nowadays are made from a synthetic elastic/cotton blend that is cheap to make but not nearly as durable and supple as denim. Real denim jeans look great and will last a long time, as long as you take proper care of them. We also recommend experimenting with different washes, shades of jeans, and ways to cuff your jeans. A nice, stone-washed look might work for one outfit while a darker shade would work for another.
Avoid trends that are outdated like baggy jeans and skinny jeans and go for classic styles like a regular boot cut or slim fit trim.
14. Learn About Brands
Knowing different brands will help you find outfits that fit your style and a lot of brands have unique characteristics, like the exact fit of their pants and the like.
Other brands might be known for their durable clothing. We are not saying that you need to pick a brand and stay loyal to them until death, only that knowing the brand landscape can help make your fashion decisions much easier.
Don’t hesitate to ask for suggestions either. We would have not been able to find some of our favorite clothing brands if we didn’t ask out friends for suggestions. Brands like Nimble Made focus on high quality, fit-focused men's shirts that are made of 100% cotton.
15. Keep Hair and Beard Manicured
A lot of men focus so much on the clothes they forget other things important to dressing well, like your hair and beard. A nice haircut or beard trim can do wonders and can actually be the thing that pulls an outfit together.
Besides, neat, manicured hair always just looks better. That doesn’t mean that you need to cut your hair or beard short. By all means, grow it out to wizard levels if you want. Just know that a brush is your best friend and that you will need to see a stylist to fix those inevitable dead ends.
If you have long hair or a large beard, consider investing in some beard or hair oil to smooth out your look. The tone of your outfit can be ruined if it looks like an ungroomed caveman is wearing it.
16. Don’t Go Overboard With Accessories
Accessories, like bright colors, can be a perfect accent to an outfit or completely drown it out by being too much. A tasteful watch or can mesh well with a particular suit jacket, but a ring, bracelet, watch, and tie clip all at once might be overboard.
Accessories are not bad but they should not have to compete for attention with one another. For example, if you are choosing a pocket square and tie, make sure that the focus and emphasis is firmly on one or the other.
The pocket square could be a slightly darker shade or the tie could have a less striking pattern. Too many accessories is like a badly composed film shot where there is no central focus or attention.
17. Buy a Blazer
We also think that every guy should have at least one suit jacket or blazer that they can mix and match with other outfits. A suit jacket is a great accessory that can turn a casual outfit into something a bit more formal almost instantly.
You can wear a blazer with some denim for a more casual outfit or pair it with some nicer slacks when you need to get more serious. A good, cool color like gray, dark blue, or brown is easy to match with other primary colors. Here are the other best suit colors to have as staples in your closet.
18. Lean into What Feels Natural and Comfortable
Dressing as a guy is tough because you want to look good, but you also don’t want to look like you are trying too hard to look good. It’s a fine line to stand on and the key is learning how to combine pieces of clothing in easy ways that look natural and not like you spent hours engineering outfits.
This is why building the basics of your wardrobe is so important. This is why we do not recommend curating your wardrobe one item at a time but buying sets that can be switched among one another.
19. Find a Tailor You Can Rely On
This goes double for your dress clothes, but part of looking great is customizing every part of your outfit, including the stitch and fit.
Try to find a tailor who can fix the fit of your clothes so they hang better on your frame. If you don't want to rely on a tailor and are a shorter guy, check out our guide on the best clothes for short men for ready-to-wear alternatives.
For example, a tailor can raise the inseam of pants, take in the sleeves for a better fit, or get a tighter fit around the chest and shoulders. A tailor can take a nice piece of clothing and customize it for you specifically. You would be surprised how many style problems can be fixed by finding a good tailor.
Here are a number of guides on figuring out if your clothes fit right and if you need a tailor:
- How to Measure Your Waist
- How to Measure Your Chest
- How to Measure Sleeve Length
- How to Measure Shoulder Width
- How a Dress Shirt Should Fit
- How a Suit Should Fit
20. Learn the Dress Codes
Dressing well isn’t just having nice clothes that fit well; it’s also about knowing how to dress for the occasion. A guy might look great in a tuxedo but he’s going to look weird if he’s wearing it at the bowling alley with his buddies.
Dressing well is partly about choosing outfits to match the implicit “dress code” for where you are going. For example, if an invite says “business casual attire,” you don’t need to wear a suit jacket and tie. There are other implications for dress codes like cocktail attire, black tie optional, business professional, and more.
Likewise, if the attire is supposed to be formal, you don’t want to wear jeans and a t-shirt. Most places don’t have an explicit dress code so it’s about learning your environment. We will say though when in doubt, it’s better to overdress than underdress.
21. Wear a Bowtie Every Now and Then
Bowties are a fun alternative to a regular tie and have a playful, ‘dapper’ appearance to them. The trick with a bowtie is how it combines nerdy and classic, a trend that is pretty common in modern style. A good bowtie can sand down the edges so you are not too formal, or make a more understated look a bit more visually interesting. A few rules on bow ties though:
- Avoid wearing a solid black bowtie with anything other than a tuxedo
- Make sure your shirt is all the way buttoned up, no open top button.
- If it’s colorful and bright, make sure it’s matched with neutral colors and patterns
- Learn how to tie it correctly and practice, practice, practice. Nothing is worse than a poorly tied bow tie.
22. Don’t Take it So Seriously
It is inevitable; you will try some outfit, look back at a picture of it years later, and wonder what the heck you were thinking. Learn to let it go. You are going to mess up when trying new styles and, yeah, you will probably end up wearing something in public that looks funny or cringey at least once.
Don’t take it too seriously though; it’s just clothes. Having the confidence to try new outfits out and not worry if they don’t turn out so well is part of the fun of building a wardrobe.
So there you have it, 22 of our best tips on style for men. We are happy that there is a changing cultural movement for men to care about their style and clothing. It can be hard for guys who were never taught how to dress themselves to learn, so you need to be open to trying new things and taking advice from others.
Over time, you will build up your own fashion sense and can start branching out, trying new styles and mixtures of old styles.