Many men find it challenging to choose what to wear. If you’re analytical, figuring out a good fashion sense and creating outfits you feel confident in can be especially daunting.
When you think about “fashion,” you might picture very thin men on a runway wearing impractical, barely-there clothing.
On the other hand, the typical tech industry uniform can be equally uninspiring, just in a different way.
Plus, depending on when you were a teenager, trends from those years likely influenced your personal style. You don’t want to look outdated or awkward, but you also don’t want to seem like you’re trying too hard, right?
What if I told you that dressing well is actually quite simple, regardless of your age, background, or income?
Here’s what I’ve learned to help you develop a good fashion sense and feel great in your clothes, based on straightforward principles that make it all understandable. I’ll even share examples from my own wardrobe later on, so keep reading!
Dressing Well ≠ Following Trends
I used to believe that fashion was all about constantly updating my wardrobe to match the latest trends. Baggy jeans are out? Time for new ones. Flannels are in? Got it. V-neck t-shirts are popular now? Okay, let’s do it.
But that’s completely wrong. And that’s actually great news. You can build a wardrobe that’s timeless, always stylish, and looks good no matter what’s currently trending.
Certain clothing styles become fashionable and then fade, and unless you enjoy keeping up with trends (I definitely don’t), your aim should be to avoid anything trendy.
The key is to honestly assess your current wardrobe and identify past trends you’re still holding onto. Then, it’s time to let them go.
Ditch Old Trends
Chances are, you’re still hanging on to some outdated trends. Here are a few common ones to consider removing from your rotation:
- Skinny jeans
- Bootcut jeans
- Jean shorts
- Cargo shorts
- V-neck t-shirts
- Elongated curved hem t-shirts
- Bulky skater shoes
- Toms shoes
These might have been stylish at some point, and they might come back again, but you’re better off getting rid of them now. It doesn’t matter if it’s “your thing” or whatever excuse you’re telling yourself… they aren’t flattering.
It’s okay to incorporate a touch of goth, hipster, or urban style if that’s your preference. However, it’s better to achieve a specific look using timeless pieces rather than relying on trendy items.
Fashion Rules to Live By
Here are some fundamental rules that will clarify why the specific style advice you’ll see later actually works:
- Maximum 3 colors per outfit (black/white can sometimes be exceptions)
- Maximum 1 pattern per outfit
- Avoid mixing warm and cold weather clothing (e.g., sandals with a hoodie, tank top with boots, jacket with shorts)
- If your top is loose-fitting, your bottoms should be more fitted. If your top is fitted, your bottoms can be looser. (However, it’s generally best to avoid extremes of very tight or very baggy clothing altogether)
- All clothing items in an outfit should have a consistent functional theme (athletic, formal, casual, etc.)
Now, let’s start building your wardrobe. The goal is to create a collection of clothes that are easy to mix and match, often called a “capsule wardrobe.” When most items can be interchanged and work well together, putting together outfits becomes effortless.
Another way to think about it is: if you were a minimalist and only wanted a few clothing items, how would you dress?
This is a great starting point, as shown in the video mentioned in the original article. We’ll focus on “casual” outfits. Athletic and formal wear are usually more straightforward.
Shirts: The Core of Your Style
A strong collection of shirts is the foundation of any good wardrobe.
T-Shirts: Essential Basics
Every man’s wardrobe needs a selection of plain t-shirts in neutral colors.
Neutral colors are incredibly versatile and easy to combine. Bright colors can overpower an outfit and are often harder to style, plus they can sometimes look less mature.
Opt for crew neck t-shirts with a relaxed fit, such as the A&F Essential Tees.
It’s important to have several essential tees in black and white. Black and white are the most versatile colors for obvious reasons, and they are also key for layering with other tops. You can also get long-sleeve versions.
Graphic tees should be minimal, subtle, and tasteful. If you choose to wear a graphic tee, it should have an artistic feel. Humorous or ironic text is better suited for younger individuals; avoid it if you want a more mature look. Also, stay away from large logos or graphics with many colors outside of your neutral palette.
Button-Up Shirts: Elevating Your Look
T-shirts are perfectly fine, especially for casual outings and warm weather. But if you want to enhance your style and achieve a more refined look, layer a button-up shirt over a t-shirt.
Depending on the occasion and weather, you can choose short-sleeve or long-sleeve button-ups. In either case, leave it unbuttoned to show the layers underneath.
Consider these versatile options:
- Denim shirts
- Flannel shirts
- Solid color and textured shirts
- Patterned and untextured shirts
Sweaters & Sweatshirts: Versatile Mid-Layers
Sweaters and sweatshirts can be worn alone, over a t-shirt, or under a button-up shirt, offering great layering flexibility.
- Crew neck and solid color sweaters
- Knit and textured sweaters
- Quarter-zip sweaters in gray or black
Jackets & Hoodies: Outerwear Essentials
Since jackets and hoodies are always worn over another top, they need to be extremely versatile. It’s best to stick with basic colors like black, gray, denim, or brown leather.
Here are some classic styles that are always a good choice:
- Bomber jackets
- Trucker jackets
- Utility jackets
- Plain pullover or zip-up hoodies
Pants: Bottoms That Matter
Moving on to the lower half of your outfit. For many men, finding comfortable and stylish pants can be challenging. The key is to keep it simple and not overthink it.
Jeans: Wardrobe Staples
Every man should own jeans in three essential colors:
- Black jeans
- Dark blue jeans
- Light blue jeans
You can’t go wrong with a straight or straight slim fit like the A&F 90s Straight Jean or Athletic Slim Jean. Resist the urge to choose super slim, bootcut, or overly loose styles. Trust me on this.
Depending on your leg length, you might need to cuff your jeans slightly so they don’t bunch up at the ankles. The ideal length is for the jeans to reach the top of your shoes and just begin to crease.
Chinos: Adding Variety
In addition to jeans, chinos are another excellent type of pants to include in your wardrobe to broaden your color and texture options.
Great chino colors to have are:
- Khaki chinos
- Olive chinos
- Navy chinos
Chinos can be a slimmer fit if you prefer, but it’s not essential.
Shorts: Warm Weather Comfort
A universally flattering style of shorts is “seersucker” in these essential colors:
- Khaki seersucker shorts
- Gray seersucker shorts
- Navy seersucker shorts
The most important thing with shorts is to avoid lengths that are too long or too short.
A good rule of thumb is for shorts to end just above your knee, which typically means an inseam between 7-9 inches. You can go a couple of inches shorter if you prefer to show more thigh.
Shoes: The Foundation of Any Outfit
If you get everything else in your outfit wrong, but you have excellent shoes, they can still save your look. Conversely, poor shoe choices can ruin an otherwise great outfit (especially running shoes in non-athletic contexts).
Shoes are also the easiest way to adjust your outfit’s formality, depending on whether you want a more dressed-up or casual appearance.
You can manage with just three pairs of shoes that will work with almost everything in your wardrobe:
- White sneakers
- Brown boots
- Sandals
Let’s discuss each one.
Sneakers: The Universal Choice
It might seem too good to be true, but white sneakers really do go with everything. They complement every color, texture, and work with pants or shorts, t-shirts or button-ups… you name it.
When in doubt, choose white sneakers.
White sneakers come in many styles and materials, but you can’t go wrong with a low-top leather pair.
If you want more versatility, consider all-black or black and white sneakers. And for a slightly different look, consider white sneakers with rubber gum soles.
Boots: Rugged and Refined
Boots can be tricky to style correctly. Too practical, and you’ll look like you’re going hiking or to a construction site. Too formal, and they might clash with the rest of your outfit.
If you choose leather boots, stick with rugged dark brown or black. If you prefer suede, opt for beige or chocolate.
Three reliable boot styles are:
Sandals: Casual Footwear Done Right
Flip-flops are fine for the beach. Slides are okay for wearing around the house. But neither is ideal for going out in public in a style-conscious way.
Birkenstocks are a great alternative that pairs well with casual tops and bottoms. Suede or leather Birkenstocks elevate them beyond typical casual footwear.
But please, for the sake of good style, don’t wear socks with your sandals (no matter how comfortable it might be).
Accessories: The Finishing Touches
Accessories are another way to enhance your style. However, it’s easy to overdo it. Many men’s fashion influencers like to wear lots of jewelry and crossbody bags (“It’s not a purse, it’s a satchel!”). Perhaps it’s old-fashioned, but excessive jewelry and bags can make men look more feminine.
However, three accessories I believe are essential for every man are:
- Hats
- Watches
- Sunglasses
Hats: Keeping It Classic
Sticking with our theme of universal and timeless style, baseball caps are the only hat style that consistently remains in fashion.
Snapbacks, fedoras, trucker hats, cowboy hats, etc., all fit very specific looks. Some are just universally unflattering (cough fedoras…) while others only suit certain aesthetics.
You can hardly go wrong with a baseball cap in any neutral color.
If you want to vary your look, get a branded hat with your favorite sports team or a distressed twill dad hat.
Watches: Timeless Timepieces
Watch enthusiasts might disagree with my recommendations, but for the average person who wants to add a little something extra to their outfit without spending a fortune, you can keep it simple.
Four essential watches that you can mix and match with almost anything are:
- Casio watches (any model)
- A black face watch
- A white face watch
- A silver or gold watch
There are many affordable options from brands like MVMT. Of course, Swiss watches are always a great choice if you want to invest more. If you’re looking to splurge, I recommend Tissot or Seiko.
Smartwatches are also perfectly acceptable. Apple Watch, Samsung Galaxy Watch, Google Pixel Watch, Fitbit, Garmin… they all look great, especially with an upgraded band and a tasteful watch face.
Any watch is better than no watch.
Sunglasses: Eye Protection with Style
I hesitated to include sunglasses here, but like hats, the wrong sunglasses can negatively affect your entire look.
Aviator, sport, and biker sunglasses don’t stand the test of time for the same reasons as fedoras and cowboy hats.
Certain styles flatter different face shapes, but these two are generally safe bets:
Of course, you can find affordable replicas on Amazon—which is perfectly fine too.
Statement Pieces: Adding Personality
Once you have the essentials covered, you can start incorporating pieces that aren’t as easy to mix and match. These are “statement” pieces that define an outfit. Statement pieces should be paired with more understated items.
Statement pieces aren’t necessarily trendy; they are still timeless, just bolder.
Examples of statement pieces include:
- A distressed oversized shirt
- A shirt or sweater in bright orange, red, or light blue
- Vintage t-shirts
- Camo pants (a personal favorite)
- Cargo pants
- Ripped jeans
- Black leather jacket
- Puffer vest
Putting It All Together: Outfit Examples
Here are a few pictures of simple outfits I often wear to give you some visual examples.
Showing a range of outfits for both warm and cool weather.
For context, I’m 6’2″ and 200lbs with an athletic build. Notice that nothing is too tight or overly fitted. While clothes shouldn’t be too baggy, a relaxed fit from top to bottom helps maintain balanced proportions.
Inspiration Sources
I highly recommend these YouTube channels for more inspiration and detailed advice:
If you still feel unsure, here’s the most basic summary:
- Solid neutral colored shirts
- Straight jeans
- White sneakers
Congratulations, you’ll never look like you don’t know how to dress again!
