Want to dress well but don’t know where to start? This simple men’s style guide reveals 10 things you can do today (without buying anything new).
Dressing well doesn’t have to be expensive. It doesn’t have to be complicated. It definitely doesn’t require you to wear a suit everyday or go out a buy a bunch of new stuff.
Want To Dress Better? Do Less!
In fact, for most guys, the best way to improve your appearance is to start subtracting, not adding. Here’s what I mean:
If you’re like most guys, you probably have a lot of clothes that you never wear.
You probably have a bunch of stuff in your closet that doesn’t fit well. You either don’t wear it, or you do wear it, but it’s not doing you any favors.
You probably have too many colors and patterns in your wardrobe.
You probably don’t know how to combine the individual items that you own.
And, most likely, you’re missing a few key pieces that will make getting dressed easier and take your style to the next level.
If you’re nodding your head right now – if any of these describe your situation – it’s okay. You haven’t done anything wrong. Most guys were never taught how to dress themselves properly (myself included).
Even the best parents often fail to pass this knowledge down to their kids, most likely because they don’t know how to dress themselves either!
Don’t worry. I’m going to lay out nine simple ways to start dressing better today.
Want to know the best part? Most of these tips don’t require you to buy anything new.
Note: if you’re a style expert, this men’s style guide will likely be too basic for you. But if you’re just getting started, they’ll be massively helpful.
Really think about each of these tips, and make it a goal to apply each of them over the next few weeks.
Once you start nailing the basics consistently, then you can start to experiment by adding colors, playing with silhouettes, wearing bolder accessories and mixing formality levels.
For now, let’s keep it simple. Here we go!
Tip #1: Size Down
By far, the biggest style mistake men make is wearing clothes that don’t fit and flatter their build.
Trust me on this one. Oversized clothes used to be a huge problem for me…
For example, most men wear pants that are 2-3 inches too long for them (especially shorter guys).
Other common problems include sleeves that are too long, shirts that are too wide, pants that are too baggy and suits that are too big all around.
The vast majority of these problems can be fixed by sizing down.
Think you’re a size medium? Try a small.
Too embarrassed to wear XS? Swallow your pride and do it. Who cares what size shirt you wear?
Wear the fit, not the label.
Clothes that fit well (which usually means smaller clothes) look better and feel more comfortable. I’m not talking about skinny jeans or painted on shirts.
I’m just talking about clothes that sit relatively close to your body and follow your natural lines and angles.
Tip #2: Wear Fewer Colors
Some guys love combining multiple bright, vibrant colors for fun, stylish and eye-catching looks. They just feel good wearing these kinds of outfits.
And that’s fine. More power to them. Seriously, it can be a really cool look.
But most guys only wear colorful clothing because they don’t really know what else to wear.
Pink polo with purple stripes? Why not! Orange t-shirt? Sure! Pastel green button up? It’s on sale – get it while it’s hot!
The fact is, bright, colorful pieces are harder to combine into outfits. They’re harder to pair with the rest of your wardrobe.
And if you wear multiple colors in one outfit, things get a bit tricky. Sometimes even one color can make you look bad. For example, guys with fair skin are easily washed out in bright, saturated colors (learn more about color here).
For the most part, color is best used in small doses. Let’s call this a “pop of color”.
The only way to use color this way is to make sure your wardrobe consists mostly of neutral colors.
By neutral colors, I mean earth tones (tan, brown, white, cream, khaki) and greyscale (black, white and grey).
You can also add olive, navy and other shades of blue, as these are just as versatile and universally flattering as true neutrals.
These neutral colors look awesome on their own – I wear all neutral outfits all the time – but they’re also easy to combine with brighter, more eye-catching colors.
You can read all about the benefits of neutral colors right here (including some example palettes and outfits).
Here’s the bottom line: when it comes to color, less is more. When in doubt, stick with one pop of color per outfit.
Tip #3: Wear Fewer Patterns
Combining different colors can be tough. Combining different patterns that have multiple colors in them can be VERY tough, even for experienced fashionistos.
My advice? Stick with solid colors for a while. This is the best way to minimize potential mismatches.
Once you get more confident about which colors go together, you can start wearing patterns (if you want to).
When you do wear patterns, try to wear one pattern per outfit. For example, if you wear a gingham shirt, wear a solid jacket over it. If you wear a plaid jacket, wear a solid tie.
You get the point.
I’d also suggest wearing patterns that only have 1-2 colors in them. For example, a navy gingham shirt has white and navy in it. It’s basically just like wearing a solid navy shirt.
A madras shirt, on the other hand, has several different colors, which makes it slightly harder to build an outfit around.
If you do wear colorful patterned shirts, be sure to keep the rest of your outfit very simple (neutral, solid colors).
But if you’re ever in doubt, just go with a solid color instead of a pattern.
Tip #4: Find a Good Tailor
My first tip was to size down, but what about all of the clothes you already own?
Maybe you have some jeans that are too long or a shirt that looks too baggy on you.
You don’t want to get rid of these pieces. After all, you paid good money for them, and they still have plenty of life left in them.
So what do you do? You take them to the tailor and get them altered for a better fit.
I’ve said it before, and I’ll say it again:
Tailoring is the secret weapon of stylish men. Ask the best-dressed guy you know if he has a tailor. I guarantee he knows them by name and visits them at least once a month.
Getting your clothes tailored can literally be a life changing experience. It was for me! And it’s way cheaper than buying new clothes.
If you want to learn how to find a tailor you can trust, read this article.
Tip #5: Upgrade Your Shoes
If you want a lot of bang for your buck, you should consider upgrading your shoes.
Most men are wearing the wrong shoes at the wrong time.
I see guys wearing athletic shoes with casual outfits or casual shoes to business casual offices, or even the dreaded flip-flops-with-jeans look.
I’m not saying you should wear “fancier” shoes. I’m saying you should wear shoes that are appropriate for the occasion.
Boom. Instant upgrade.
Want to wear slip ons to the airport? Go for driving mocs, not those square toe loafers you bought with that JC Penny gift card your sister gave you for Christmas three years ago.
And no…no slides. They weren’t cool back in the day, and they’re not cool now, no matter what logo they have on them (looking at you, Gucci).
Not sure what shoes to wear? Get yourself a pair of brown leather chukka boots. They might feel weird at first, but I bet they’ll become the most worn pair of shoes in your closet.
Or go check out my post about building a minimalist shoe collection.
Just remember: your shoes work hard. So make sure they’re working for you, not against you.
Tip #6: Add an Accessory
One of the easiest and most effective ways to dress up an outfit is by adding accessories.
I’m talking about watches, ties, pocket squares, bracelets, rings, necklaces, hats and various other functional-but-probably-not-totally-necessary items that men tend to wear.
Even a boring outfit can be transformed and elevated with accessories. When you add an accessory or three, you’ll look so much more put together (but not like you’re trying too hard).
My go-to accessories are watches and sunglasses. These are super practical and look great with any type of outfit, no matter how casual or formal it is.
A simple cuff style bracelet is also a great accessory for men. Eyeglasses also work well, even if they’re just for reading or looking at screens.
If you’re wearing a suit, go with a tie and maybe a pocket square (when in doubt, go with a solid white square).
Tip #7: Remove an Accessory
Be careful with that last tip, my friend. It’s easy to go overboard with accessories, especially when you first start getting into men’s style.
I see lots of menswear noobs and fanatics wearing a watch, a stack of bracelets, a hat, pocket square and tie, plus a fedora for good measure.
When you do this, it almost looks like a costume – and not in a good way.
Go with 2-3 tasteful accessories, max (i.e., watch + tie + sunglasses). When in doubt, just remember that less in more.
Like fashion designer Coco Chanel famously said:
Before you leave the house, look in the mirror and take one thing off.
The lady knew what she talking about, so I recommend heeding her advice!
Tip #8: Learn the Dress Code
Great style is like a great referee: it shouldn’t make mistakes.
So much of dressing well is just dressing appropriately for the occasion.
Have you ever seen someone at a wedding with an untucked shirt or casual shoes? They stick out like a sore thumb.
Similarly, there’s always the guy who went way over the top with a brightly colored three piece suit, pocket watch, velvet slippers…
Both of these people are totally missing the mark and, ultimately, disrespecting the wedding party.
The underdressed guy lacks respect for the formality of the event. He should’ve read the dress code on the invitation!
The overdressed guy wants attention, but it’s not his day. All eyes should be on the bride and groom, not some overly tailored peacock.
Understated is almost always the way to go:
Think about where you’re going. Is there a dress code? Maybe it’s explicit (a wedding), or maybe it’s unspoken (a job interview).
When in doubt, ask.
In most situations, the goal isn’t to impress everyone with your style. Even on a date, you want to look good, but you don’t want to overdo it.
Bottom line: try to dress appropriately for the occasion, even if it means you can’t wear exactly what you want to.
Tip #9: Layer Up
I’ve said it before, and I’ll say it again:
Just like tailoring, layering is the stylish man’s secret weapon.
That’s why most guys who are into style love fall more than any other season. Cool weather means you get to wear layers without overheating, and layers look amazing (when done right).
Here are some easy layering ideas anyone can pull off:
- Sweater > button up shirt
- Jacket > sweater > button up shirt
- Vest > work shirt
- Work shirt > henley
- Jacket > vest > henley
The possibilities are endless, and you can always check out the outfit archive for ideas and inspiration.
Tip #10: Trend Carefully
There’s really no such thing as “timeless” style. You can buy clothes that will still good in 10 years, but 100 years? Probably not.
That said, men who dress well tend to avoid getting into every single fashion trend that hits the shelves.
I’m not saying that you should never experiment with fashion trends. Experimenting with new colors, fabrics and silhouettes can be a great way to add new life to your wardrobe.
Some trends, like the slim/cropped look, have worked really well for me.
But trends come and go faster than ever these days. It’s expensive, wasteful and time consuming to keep up with all of the latest styles.
A well-dressed man tweaks his wardrobe slowly over time. He doesn’t replace everything he owns every time H&M drops a new collection.
If you do want to test out a new trend, such as looser fitting pants, try dipping your toes with one item before investing too much time or money.
When Our Powers Combine…
These tips for how to dress well may be simple, but when used in tandem, amazing things happen. We’re talking multiplication, not simple addition.
For example, if you combine layering with great color combos and proper fit, I can almost guarantee you’ll be one of the best dressed men in any room.
Actually, scratch that. I do guarantee you will be one of the best dressed guys in any room. Most guys can’t even figure out one aspects of style, let alone all three.
It’s not because they’re stupid. They just haven’t put the time in. Maybe they don’t care, or (more likely) they just don’t know that they don’t dress well. I didn’t know until my mid-20s. No one ever tells you this stuff.
But you’re reading this, which means you are willing to put in some time, energy and even money. So study these tips again, then start working on them.
And remember: it’s a marathon, not a sprint, so have fun and enjoy the journey 😉
Questions About Dressing Well As a Guy
Here are answers to some of the most frequently asked questions about how to dress well as a guy:
How Can I Learn To Dress Well?
Focus on how your clothes fit. This is the most important aspect of style. Find a good tailor, and get the clothes you already own altered so they fit better.
What Makes One Well-dressed?
Well-dressed men wear clothes that fit their body properly, and they put together outfits using coherent, pleasing color combinations.
How Can I Become More Stylish?
Get your clothes tailored. Don’t wear too many colors at the same time. Wear 1-2 tasteful accessories (but not more than that).
Why Is It Important To Be Well-dressed?
Like it or not, the way you look influences how other people see you. It can make or break a first impression. It also influences how you see yourself. Well-dressed men tend to have a more positive self-image. Dressing well can increase confidence.
How Do I Motivate Myself To Dress Better?
If you’re reading this, you’re already more motivated than most people! Focus on quick wins: go get a few of your favorite pants and shirts tailored. Once you see how much better they look on you, you’ll feel even more motivated to keep improving your appearance.
How Can I Dress Well Without Trying?
Dressing well takes some effort at the beginning. After awhile, it becomes more effortless. If you want to look like you’re not trying too hard, try to not wear too many accessories (2-3 max) or too many colors at the same time, and overly trendy outfits and hairstyles.
Questions? Comments? Leave them below!
I stumbled onto this site yesterday while looking or info on watches. I’m actually tall, 6 ft 3, but there’s a lot of solid advice here for any guy, regardless of height.
Love your writing.
Niall Jenkins says
I’m thankful that you mentioned in your article how it is possible to both over and under-dress when attending an event. My boyfriend recently told me that he was interested in getting some new clothing for an event that is coming up, but he is unsure of what vibe he wants to go for. I’ll be sure to do some research and find a reliable clothing store that would be beneficial to what he needs!
Great article Brock. “dressing up ≠ dressing well” is an excellent way to think when you want to dress well. I am super impressed with little nifty tricks like remove the accessory. Please continue writing great articles.
“Find a tailor.” Another option is to do some of the alterations yourself. I’m not a young man, but just a few years ago, I decided to buy a sewing machine. I took two private lessons to learn how to use it. Since then, I have shortened and tapered a lot of nice shirts and trousers that were in my wardrobe but which didn’t fit that well. Vast improvement…and not that hard to do.
I love Clark’s Desert Boots/Chukka Boots, but they do not come in extra wide (which is what I need). Any suggestions? Any other brands that would fill the bill?
Hi Adam, I searched Shoes.com and there were some other brands in extra wide. Not as many colors. I have short, wide feet, so it’s frustrating how a foot size limits our style.