Many men struggle with what to wear. The more left-brained you are, the more overwhelming it is to try to figure out how to have a good sense of style and put together outfits that you feel good in.
When you think of "fashion," you probably think of anorexic-looking men walking down a runway wearing ridiculous pieces of fabric that barely even resemble clothing.
Unfortunately the typical silicon valley uniform is just as bad, just in different ways.
Plus, depending on which decade you grew up in, there were fads and trends that dominated your formative teenage years and likely had a huge influence on your own sense of style.
You don't want to be stuck in the past, you don't want look like a dork, but you also don't want to look like a try-hard, right?
What if I told you that it's actually pretty easy to dress well no matter what your age, ethnicity, or income bracket is?
Here's everything I've learned to help you feel good in what you wear and develop your own sense of style, while being grounded in simple principles that help you make sense of it all.
DISCLAIMER: I certainly don't claim to be a perfect example of great style. But I can say with confidence that I'm definitely not in the "dresses dorky" category any more.
I used to think that it was all about updating your wardrobe to keep up with whatever was "in" at the moment. Super baggy jeans are out? Okay time to update. Flannels are in? Got it. Now everyone's into v-neck tee shirts? Alright, here we go.
But this is the furthest thing from the truth. And this is the best news you could have hoped for. You can build a wardrobe that is timeless, always in style, and looks good no matter what happens to be in or out.
Certain styles of clothing items go in and out of vogue, and unless you actually like keeping up with trends (I certainly don't), then your goal should be to avoid anything trendy.
Now, the real unlock here is taking a good hard look at your wardrobe today and evaluating which trends you've embraced in the past. Then let them go.
Odds are, you're probably still holding on to old trends. Here are some of the common ones:
They may have been in style at one point, and they might be again at some point, but you're better off abandoning them altogether. I don't care if it's "your thing" or whatever rationalization you're making to yourself... they don't look good.
It's okay to have a little flair of goth, hipster, urban, etc if that's your thing. But it's better to go for a certain look using timeless pieces than to go for that same look using trending pieces.
Here are some basic rules to follow that will also enlighten why the prescriptive advice you'll see further down makes sense:
Okay, now let's start to assemble your wardrobe. The goal here is to assemble a collection of items that are easy to mix and match, also known as a "capsule wardrobe." When items are easy to interchange and most things work well with each other, outfits are effortlessly put together.
Another way to think about it is if you were a minimalist and wanted to limit yourself to just a handful of clothing items, how would you dress?
This is a good foundation to build on, as seen in this video below.
We'll stick to the "casual" outfit category. Athletic and formal wear is a little more straightforward.
The foundation of every good wardrobe is a solid collection of shirts.
Every wardrobe needs a collection of plain tee shirts in neutral colors.
Neutrals are incredibly easy to mix and match. Vibrant colors can dominate a look which will make or break it. Plus, vibrant colors tend to look a little more childish.
Go with a crew neck and relaxed fit like these A&F Essential Tees.
It's worth pointing out here that you should have multiple black and white essential tees. Black and white are the most versatile for fairly obvious reasons, but they're also the staples for layering with other tops.
You can also pick up long-sleeve versions as well.
Graphic tees should be limited, subtle, and tasteful. If you're going to wear a graphic tee, it should have an artsy feel. Ironic/funny text is fine for 12 year olds, but avoid it if you're going for a more mature look. Also avoid giant logos or graphics that have a lot of colors outside of the neutral color palette.
Tee shirts are fine on their own, especially for super casual outings and warm weather.
But if you want to take your style up a notch and go for a more sophisticated look, layer a button up over a tee shirt.
Depending on the occasion and weather, you can go with either short sleeve or long sleeve. But in either case, leave it unbuttoned so they layers are easily seen.
They can be worn alone, over a tee shirt, or under a button up.
Since jackets and hoodies are always thrown over another top, they need to be super versatile. So it's best to stick with basic colors like black, gray, denim, or brown leather.
Here are some universal styles you can't go wrong with:
Now onto the bottom half of your outfit.
Personally, this was one of the harder parts for me to feel comfortable with. The key is to not overthink it.
Everyone should have jeans in three essential colors:
Depending on your leg length, you might need to cuff your pant legs a bit so they don't look like the top of a bendy straw. The goal should be to fall onto the top of your shoe so it just starts to crease.
Additionally, chinos are another great pant to have in your collection to round out your color and texture selection.
Chinos are great in three essential colors:
Chinos can be on the slimmer side if you prefer, but it's not necessary.
A universally great style of shorts is the "seersucker" in three essential colors:
The biggest thing about shorts is not to go too long or too short.
A rule of thumb is to sit just above your knee, which has the inseam between 7-9", but you can go a couple inches above that depending how much thigh you want to show off.
If you mess up everything else about your outfit but you still have a solid choice of shoes, they can salvage everything.
On the flip side, a bad choice of shoes will absolutely ruin your 'fit (looking at you, running shoes).
Shoes are also the best way to dress up and down your outfit depending on how formal or casual you want to look.
You can get away with owning only three pairs of shoes that could be paired with virtually everything in your wardrobe:
Let's talk about each one.
It feels too good to be true, but white sneakers go with everything. They work with every color, every texture, pants or shorts, tee shirt or button up... everything.
When in doubt, slip on a pair of white sneakers.
You can get white sneakers in many different shapes and material, but you absolutely can't go wrong with a low top leather pair:
If you want to add a little more versatility, you can also get an all black or black and white pair. And if you're feeling extra adventurous, get a rubber gum sole pair as well.
Boots are difficult to get right. Too functional and it looks like you're going on a hike or to a construction job. Too fancy and it starts clashing with the rest of your outfit.
If you're going with leather, it's best to stick with a rugged dark brown or black. If you're going with suede, stick to beige or chocolate.
Three tried and true boot styles are:
Flip flops are fine for going to the beach. Slides are fine for walking around the house. But neither are great for going out.
Birkenstocks are a great option to pair with more casual tops and bottoms. The suede or leather options elevate it beyond your usual sockless footwear.
But please, for the love of all that is good, don't wear socks with your sandals (as comfy as it is).
Another way to elevate your style is by accessorizing. Personally, I think it's easy to go overboard here. A lot of the men's fashion gurus love to wear multiple jewelry items and cross-body bags ("It's not a purse, it's a satchel!"). Maybe I'm old school, but I think bags and excessive jewelry make men look more feminine.
Three accessories I do think are essential for every many, however, are:
Sticking with our universal and timeless theme, baseball caps are the only style of hat that don't fall in and out of style.
Snapbacks, fedoras, truckers, cowboy hats etc... they all fit very particular looks. Some are just universally bad (*cough* fedoras...) while others only fit a certain aesthetic.
It's hard to go wrong with a baseball cap in any neutral color.
If you want to mix it up, get a branded hat with your favorite sports team or distressed twill dad hat.
Watch aficionados will crucify me for what I'll recommend but for your average joe like myself who just wants something to add a little something extra to their outfit without breaking the bank, you can keep it pretty simple.
Four essential watches you can mix and match with most everything are:
There's also nothing wrong with a smart watch. Apple, Samsung, Google Pixel, Fitbit, Garmin... they all look great. Especially with an upgraded strap and a tasteful watch face.
Any watch is better than no watch.
I hesitate to include sunglasses in here but, like hats, the wrong sunglasses can throw off everything else.
Aviator, sport, and biker sunglasses fail the timeless test for the same reason as fedoras and cowboy hats.
Certain styles look better on certain face shapes, but it's hard to go wrong with these two:
Of course you can pick up knockoff replicas on Amazon — nothing wrong with that either.
Once you've nailed the essentials, you can start to branch out into pieces that don't mix and match well.
These are pieces that dominate the entire outfit, so they're called "statement" pieces. Statement pieces have to be combined with very subtle pieces.
Statement pieces aren't necessarily trendy. They're still timeless, they're just a bit on the bolder side.
Statement pieces could be things like:
I can't recommend these three YouTube channels enough for examples and more specifics:
If you still feel lost, this is the absolute gist of it all:
Congrats, you won't look like a dork anymore!