Before we really get into this, a few disclaimers:
Games are a prerequisite! You won’t drastically improve your dating by upping your style UNLESS you have the ability to approach, close, and interact with women while being a generally cool dude.
Style is a supplement that can get you to that next level, but only once you have the fundamentals. Like a catchy ad, it can get you attention and a decent first impression… but can’t make the full sale for you.
This is written from my perspective, a guy that likes to travel around and date freely. A lot of my interest in fashion/style has stemmed from continuously trying to improve my dating life. It is in this frame of mind that I write this post, so because of that some of the motivations/goals might not fit perfectly with yours.
Don’t get me wrong, if you’re married or not actively dating then this post will have PLENTY of useful style gems in it for you. Upping your style game isn’t exclusively for the ladies (although if I’m being honest it’s easily 80% for me), as your professional and personal lives will thank you in less obvious ways.
Your Style Archetype
James Bond, David Bowe, John Legend, Donald Draper.
Finding your own style isn’t something that just develops naturally. For most people, it’s cultivated over time. The way we do this is by breaking up different ‘looks’ into style archetypes and seeing what suits us best.
The easiest way to get into this is to review a few of the biggest style archetypes for men. From there you’ll be able to see where you fit.
*Note* you don’t have to pick a single archetype. The beauty of fashion is that it enables you to bounce between different categories, and look good in each one. You can fit into these archetypes in different environments by molding your style however you want to be perceived.
Let’s walk through a few archetypes below so you get the idea.
Club Promoter / Bad boy
Casual Don Draper
The Clean Cut Millennial
So How the Hell Do I Get ‘Good Style’?
This is the biggest brain breaker of fashion for most men. Two qualities of fashion constantly baffle our analytic minds and beat us into submission when it comes to picking clothes.
1. The rules of fashion are implicit (style isn’t written down in a manual).
2. It’s ever-evolving.
So we are often relegated to searching around and piecing our wardrobes together through a few blog posts, gifts from family or ex-girlfriends, and the occasional ‘necessity’ purchase made in a hurry.
Some of us actually make an effort to shop, but we have NO IDEA where to begin, what to start with or any instinct as to what looks good.
So how do we develop an instinct when we clearly aren’t born with it? Is it even possible?
Let me smack you in the face with some harsh reality. Fashion sense isn’t an innate ability that only women possess. Anyone can develop it by spending some time observing clothes/styles/fashion.
Do you think your girlfriend is such a competent interior designer because she was born with the ability to find a cute table to match the rug? No. Not even close.
The real reason is because before your dearest chose that table, she spent a cumulative 19 billion hours on Pinterest looking at cool modern home design photos.
After about 12 billion hours, she starts getting a feel for what’s cool and what’s not. Past hour 15 billion she starts to develop a taste and style of her own.
You may be scoffing now at my exaggeration of Pinterest hours (or was I?) and thinking there’s no way in hell you’re going to put in the time ‘looking at clothes’ to develop this skill.
Fair enough my friend. Let me propose a concrete method that will get you enough without taking over your damn life looking at pictures of khaki/belt combinations.
Allow me to present the Instagram fashion builder extreme plus silver program…
Using Social Media to Scout Out Styles
If you’re a man reading this it’s very unlikely you are a regular Pinterest user. So let’s stick to good ole Instagram for our style snooping.
Find and Follow Current Brands You Love
The easiest way to keep up with a brand or style you love is to follow them and see all their latest products and updates. Get rid of all the hot babes on your explore page, and watch as Instagram inevitably starts to market you their competitors/related brands and styles. Boom, that’s as simple as it needs to be for you to get started.
Follow a Few of the Syndicator Men’s Fashion Accounts
There are a ton of massive men’s fashion accounts on the gram. They are mostly built to promote eCommerce stores/models… but they will flood your feed daily with incredibly well dressed dudes in a variety of styles.
They won’t all resonate with you (nor should you try and copy everything you see) BUT after a few weeks of even just noticing these photos in your feed you’ll start to passively develop a taste for what you think looks cool and what looks stupid.
Here is a list of accounts you could check out to get an idea of what I am talking about (ignore the generic account names):
The idea is to start getting pictures of mens fashion flooding your explore page so you get the idea of what to look for.
You could also just type in ‘mens style’ in the Instagram search bar and explore it for yourself!
Grailed.com – The Pulse of Men’s (High) Fashion
Grailed is a marketplace for high end men’s clothing. Yes, this means designer and (some) insanely overpriced clothes.
Designer Tees on this site can run in the several hundred dollars range, used.
But just because it has a lot of high end products for sale does not mean Grailed is useless to the budget conscious of us.
Because Grailed sells the hottest styles and brands, it becomes insanely useful to those of us trying to figure out what even IS hot these days.
After some thoughtful browsing on Grailed, you should at least be aware of who the famous brands/designers are and whose style you dig (you went and looked them up on Instagram right?).
The staff at Grailed handpick items to feature daily AND write blog posts that provide an in-depth treasure trove of current fashion knowledge.
Spend some time on this site if you really want to put your finger on the pulse of the higher end men’s fashion market.
Nuts and Bolts of Fashion
This section is going to cover a few of the most basic things when it comes to perfecting your looks.
Avoid the Biggest Mistakes
The fundamentals of fashion are actually pretty simple. It’s more about not messing up than it is about doing the right thing. Let’s just run through some of the biggest/obvious faux paux that will crush your style always.
Sock styling varies a lot these days. Generally you want to go with ‘no show’ socks, especially when wearing sneakers. High socks only really fit into a younger man’s ‘street’ style of dressing, or sometimes while wearing sneakers and in your workout clothes (unless you have stick legs).
You want to be mindful of the color of your socks too. If you wear white shoes, wear white ankle/no-show socks. If you wear black shoes, wear black socks. However, if you are wearing more formal attire such as a suit you want to match the color of your socks to the color of your pants. A navy suit must be matched with navy socks.
This is a mistake that’s easy to say but harder for someone to truly understand. I’ll try and illustrate it with a few images. Bad fit for men usually means:
-Oversized pants (too baggy, too long)
-Incorrectly sized or tailored shirts (very baggy sleeves, too short on the torso etc.)
As functional creatures, generally as men we hold onto too few pairs of shoes for too long. An overused or dirty pair of shoes is a dead giveaway that you’re not committed to looking your best.
*Note* ratty shoes CAN be pulled off in certain styles.
For those of you that aren’t into shoes and dread picking new ones, a few bullets:
-You can’t go wrong with clean, white sneakers
-Black converse/chucks work with just about anything
-A good pair of leather boots go a long way (dress them up or down depending on the occasion!)
Fit – The Most Important Aspect of Your Clothes
Here’s something that isn’t common knowledge. The fit of your clothes matters 100x more than the brand/fabric/style/color of your clothes.
I’ve heard guys lament about the costs of ‘nice clothes’ as a justification for what they’re currently wearing. This is only a partial truth.
As a man, you are supremely fortunate that to look great you don’t need to be wearing designer labels or even anything out of the ordinary.
You can make a girl’s knees weak with a crisp and well fitting white T-Shirt and decent jeans (trust me on this, there’s a percentage of women who LOVE this look). The value some women place on labels/designers does NOT unilaterally translate over to men’s fashion. Use this to your advantage.
There are really only two reasons men lack good fit in their current clothing:
-Ignorance (no framework of what a ‘good’ fit is).
but more likely…
-Lack of patience to FIND a good fit.
Think about this for a second. If you were given two different shirts to wear (one that fit and one that didn’t) are you really going to tell me you couldn’t pick the correct fitting one? Unlikely.
This comes down to the fundamentals of shopping and clothes selection. Most men simply don’t spend the time trying different sizes/cuts of their clothes. We prefer to just get it done, grab a medium and move the fuck on with our lives.
Or we order one size online and it’s ‘close enough’, so we stick with it rather than jumping through all the hoops of online shipping + returns.
I totally understand this approach (and am guilty of it too), however if you really want to maximize your wardrobe you must become more focused on finding the right fit.
This means trying on 5 different styles of jeans (and multiple sizes of each jean) before picking the winner.
It also means buying multiple sizes of the same shirt online (and planning to return the ill-fitting ones after you’ve tried them all).
Is it more of a pain? Hell yes. Is it worth it to improve your look? You guessed it, hell yes.
Pro tip: Shop online at places that offer legitimately free returns/shipping. Then buy 3 sizes of EVERY item. Your typical size, one up, and one down. Then just return the 2 sizes that don’t fit when you’re done and get your money back.
Colors And All That Matching Nonsense
I’m not going to belabor the color wheel and matching colors. If you’re really that into it you can google it and come across thousands of men’s color style guides.
What I WILL tell you is this:
-3 color outfits are a degree more complex to matching than 2 color ones. If you aren’t sure then stick with 2 colors (shirt, pants, shoes)
-It’s far easier to learn a list of colors that match and which don’t.
So without further ado, here are my quick and dirty color matches to save you time and keep things simple.
Black is your friend
Black goes with everything except brown. An all black outfit is fine (I have some friends who pretty much only wear black), though it can be made to look awesome with a nice pair of clean, white sneakers.
White is also your friend
Pick any accent color (blue, red, yellow, purple) and pair it with white without worry.
Easiest two color combos:
-Black and anything.
-White and anything.
-Black and Gray.
-Green and Khaki.
-White and Navy.
-Black and White.
-Gray and Pink.
Color combos to avoid:
-Red and Green.
-Red and Orange.
-Green and Orange.
-Brown and Black.
-Purple and Yellow.
For a woman to have ‘great style’ and clean look, she has to have a wide variety of outfit options and shoe combos.
Fortunately for us fellas, a guy can look amazing with a clean crispy t-shirt (that fits), cheap ripped jeans (that fit), and FRESH shoes.
This is one the biggest style tips that most guys miss. Since we often see shoes more as a utility, we don’t replace them until they’re beaten to hell.
Stop doing this. If you want to look great (especially if you’re out there dating), clean and new shoes are a huge boost to even the simplest outfits for a man. Black shirt, black jeans, a cool hoodie, and nice white shoes make you look like a well styled guy on a date. Replace the shoes with some dirty beat up ones and you start to enter scrub territory fast. Trust me, girls notice shoes!
So buy some cool shoes, keep them clean and replace them early. Pretty easy being a guy right?
And guess what other beautiful gift the world has given us men when it comes to shoes…
No one gives a shit about what brand.
As a guy you don’t get too many bonus points for having name brand shoes. Generally, if they’re styled well and clean you can’t go wrong.
So what styles/kinds should you buy?
We need to go back to our style archetypes to really nail down exactly which shoes to buy, but generally you’ll want:
-One pair of super clean white sneakers.
-A pair of more ‘street style’ sneakers in a black or blue.
-An all black ‘chuck’ style sneaker for going out/night clubs etc.
-Dressier styled boots (high quality leather, or suede trimmed).
Jewelry and Accessories
One of the easiest things you can do to up your style is by actually wearing more jewelry than that one watch you wear with everything.
Guys are generally hesitant to wear any more jewelry and I’m not exactly sure why. Maybe it’s not knowing what to buy, maybe it’s fear of being seen as too feminine? Or maybe it’s because they think they might look weird wearing a gold necklace. Amateur psychology over.
What I DO know for sure is that well chosen jewelry can seriously improve your look and women ALWAYS notice.
You don’t have to buy a Rolex
The beauty of being a guy (one of several) is that you don’t need branded or expensive jewelry in order to look good.
Most styles for men that look good are sterling silver and black (both cheap). Gold can be plated (or outright fake) and not an issue. I buy rings off of aliexpress.com for $1 a piece that get as many compliments as my $100 rings.
Where to Find Good Brands
This is up to your personal preferences. Instagram is your friend again here. Nowadays there are tons of direct to consumer watch and jewelry brands that sell cheap, good looking gear.
Be warned, a LOT of the jewelry you see sold on Instagram for $50 bucks can be had for pennies on AliExpress. Watches are not so likely.
To get started you can look at big brands like Ted Baker, Timex, etc. Things carried at high end department stores like Nordstroms are always a safe bet (and not always overpriced).
Remember, it is about how the jewelry fits into your outfit, rather than how expensive or branded they are.
It is shocking that many men simply ignore the importance of personal grooming. Women (actually everyone in fact) notice when you are not properly groomed. If you are not adequately grooming yourself, women will likely be less attracted to you, your colleagues will respect you less, and you will likely not feel as confident as you would like to feel.
The Basics of Men’s Grooming
First ensure that you have showered, used soap, brushed your teeth (and flossed), washed your hair with shampoo and conditioner, used deodorant, and groomed your facial hair if you have any (avoid any weird overly groomed styles). These are non-negotiable. You want to be presented well, and look like you have made an effort to do so.
You should also ensure that you have properly trimmed your nails (both hands and feet), plucked any unwanted hair in between your eyebrows, shaved any neck and back hair that may be showing, and cleaned up your family jewels with a body grooming tool and some ball powder. Use a quality lip balm to make your lips look healthy, apply sunscreen on your face with moisturizer in it if you go in the sun, and always carry gum if you will be out drinking or eating and interacting with people.
You should also have as healthy a diet as possible, and ensure you regularly exercise (daily if possible). A good body can seriously up your appeal. I’m not saying you have to have a six pack to be fashionable, simply pointing out that if you’re in decent shape and fairly trim then clothes will fit you better and you will SEEM more put together.
Taking Grooming to the Next Level
If you want to up your grooming game even further to stand out, there are couple of things you can do.
-Blowdry, comb and put styling products in your hair.
-Use anti-aging serums (look them up!),
-Use face and hair masks.
-Get your teeth whitened.
-Get laser hair removal therapy (super effective).
Nomad Style – Making it Work On The Road
This is where shit gets interesting. If you thought having good style as a guy was tough before, try doing it when you have to carry your entire wardrobe around in a suitcase.
How to manage this while living out of a suitcase
Space is a premium (obviously) so we have to do what we do best as Nomadic Entrepreneurs. 80/20 the shit out of our clothes. Get rid of stuff you know you wont wear, even if you have that one possible scenario you think you might need it.
Buy Cheap, Quality Clothes When You Get There
This is the easiest way to make sure you’ve got great clothes when traveling. Simply go out and buy new stuff as you need it.
If you’re going to spend a few months in a city, this is what I recommend. You can hit the mall for one afternoon and end up with enough options to last you months. There could even be an awesome local clothing store with some great items to add to your wardrobe (or suitcase I should say).
Now the obvious issue here is cost. You can’t go out and buy 10 polo shirts every 8 weeks as a traveler…
BUT fortunately for you, in most of the western (and even some in eastern) worlds there are cheap and ‘trendy’ department stores. Places like Zara and H&M litter the globe and offer cheap options that look great.
Invest in High Value Pieces
The other option available to you is to buy a few really high quality and versatile pieces that you always have with you and always look good.
This can vary a lot based on the kind of climates you spend time in but a few I always spend on:
-Designer Hoodie/Zip Ups/jacket.
-One pair of dressy loafers (if in a summer climate).
-One great watch.
-Collared shirt (not some tech fabric, but either nice linen or refined wool).
-One awesome pair of jeans (two max).
The ‘basics’ like T-shirts and other wardrobe pieces I just grab cheaply when I get there and rotate as needed. It is still good to keep 1-2 white, black and navy t-shirts though.
If you take this approach, you’re essentially maximizing your luggage storage and your ‘style’ while minimizing the amount of money you need to spend in each city on new clothes.
That’s an 80/20!
A Note on Shoes
You’ll notice that I had boots in my list of high value pieces but NOT sneakers/shoes. This is because sneakers are a major pain for travelers. 3 different pairs will fill up your suitcase unnecessarily.
For me, it’s easier to buy cheap shoes at a place like Zara (stylish shoes that don’t last long cost about $25-$35). Buying basically disposable shoes in each place lets you have a bunch of different styles and colors to mix up your outfits. However, you could still have one pair of gym/running shoes you take with you.
And as I mentioned above, if you’re like me and a single guy dating, good shoes make an impression on your dates (women always notice your shoes). Easier to have clean new ones in each city than to try and nurse the same three pairs around the globe.
Some Travel Fashion
The 80/20 of Style
Remember the 80/20 rule. Yes I said it. You should ask yourself what small percentage of items can you buy/wear that has the maximum amount of impact on your style.
Let’s recap some of the key points for your fashion success while traveling (that don’t require a big wardrobe).
Know the style of where you’re headed
Every country has a distinct style, and with that come a few rules you should never break. For example in Colombia you would NEVER wear shorts. Do some quick research before you head to a new country. I’m sure there are only 19 thousand travel blogs analyzing fashion in that particular city.
Do designer brands matter?
Remember the answer is pretty much no, with one small exception. Obviously 97% of men will have no idea and not even notice what you’re wearing (men that work in the fashion industry are the exception). Pretty much the same goes for women, though I’d put it at maybe low 90s.
The only time I’d really say to put effort into picking designers/brands is if you really want to go out and pick up higher end fashion models that may be more common in the area such as SOHO New York or the social circles or venues you are in while traveling. These women DO notice designers, and some of them will judge you on it (I’ve been schooled more than a few times). But unless that’s your game I say go for value/quality and your dating life won’t know the difference.
How do we do it all on a budget? As I’ve mentioned, you should definitely find 2-3 pieces you spent big on that last year (stylish jackets, sweaters, hoodies, jeans etc.). For the rest, you can find cheap stuff at Zara or the equivalent.
Get it tailored
Take all of your clothes, jackets, pants to the highest rated tailor you can find and have them alter them. This never costs a ton, and can make a $100 jacket look like $2500. Start making trips to the tailor a habit after you buy new gear.
So that wraps it up! By reading this guide you should be one step closer to having incredible style wherever you go in the world. This guide is by no means an exhaustive guide, so you should continue with your own research and remain consistent in building your knowledge of fashion. If you implement the things discussed in this guide, you will see immediate results with women and in life, I promise!