Many men find the world of fashion and style confusing and overwhelming. If you’re someone who prefers logic and practicality, figuring out how to dress well and create outfits that make you feel good can seem like a daunting task.
When “fashion” is mentioned, images of runway models in avant-garde, impractical clothing might come to mind.
And while the casual tech industry uniform might be more comfortable, it often lacks style and can be equally uninspiring.
Growing up, you might have been influenced by fleeting trends, making it hard to define your own style without feeling outdated or like you’re trying too hard.
But what if dressing well wasn’t as complicated as it seems? What if you could develop a timeless personal style, regardless of your age, background, or budget?
This men’s style guide will provide you with the essential principles to feel confident in what you wear. It’s about building a wardrobe based on simple, enduring concepts that will help you make sense of style and develop your own look.
Dressing Well Is Not About Chasing Trends
A common misconception is that dressing well means constantly updating your wardrobe to keep up with the latest trends. Thinking you need to swap out clothes every season to stay “in style” is far from the truth. This approach is not only exhausting but also unsustainable.
The best news? You can create a timeless wardrobe that remains stylish and looks great regardless of fleeting fashion trends.
Fashion trends are cyclical. Certain clothing styles become popular and then fade out of vogue. Unless you genuinely enjoy keeping up with these trends, your goal should be to build a wardrobe that transcends them.
The first step is to honestly assess your current wardrobe and identify any past trends you might still be clinging to. It’s time to let go of those outdated pieces.
Time to Ditch These Old Fashion Fads
Many men unknowingly hold onto outdated trends. Here are some common items that might be aging your style:
- Skinny jeans
- Bootcut jeans
- Jean shorts
- Cargo shorts
- V-neck t-shirts
- Elongated curved hem t-shirts
- Bulky skater shoes
- Toms shoes
While these items might have been fashionable at some point, and could potentially make a comeback in the future, it’s generally better to move on from them entirely. Personal style is about more than just “your thing”; it’s about presenting yourself in a way that is both current and timeless.
It’s perfectly acceptable to incorporate elements of subcultures like goth, hipster, or urban into your personal style. However, it’s more effective to achieve these looks using classic pieces rather than relying on trendy items that will quickly become dated.
Essential Fashion Rules for Men
Understanding a few basic fashion rules can significantly simplify the process of dressing well. These rules also provide the logic behind the style advice you’ll find later in this guide.
- The 3-Color Rule: Limit your outfit to a maximum of three colors. Neutrals like black and white can often be considered exceptions as they serve as foundational colors.
- One Pattern Per Outfit: Stick to a single patterned item in your outfit to avoid visual clutter and maintain balance.
- Weather-Appropriate Clothing: Avoid mixing items designed for different seasons. Sandals with a hoodie, a tank top with boots, or shorts with a winter jacket are examples of weather-inconsistent combinations to avoid.
- Balance Baggy and Slim Fits: If you wear a baggy top, pair it with slimmer bottoms, and vice versa. However, in general, it’s best to avoid extremes in either direction – overly baggy or overly slim clothing often looks less refined.
- Consistent Functional Theme: Ensure all items in your outfit align with a consistent theme, whether it’s athletic, formal, casual, or somewhere in between. Mixing athletic shorts with a formal dress shirt, for example, breaks this rule.
Now, let’s begin building your wardrobe. The aim is to create a collection of versatile pieces that can be easily mixed and matched, often referred to as a “capsule wardrobe.” When most items work well together, putting together stylish outfits becomes effortless.
Think of it this way: if you were a minimalist aiming to own only a limited number of clothing items, how would you dress?
This minimalist approach provides a strong foundation for building a versatile and stylish wardrobe, as demonstrated in many men’s style guides and videos.
For the purpose of this guide, we’ll focus on “casual” style. Athletic and formal wear, while important, often have more straightforward guidelines.
Shirts: The Core of Your Wardrobe
A well-rounded collection of shirts is the cornerstone of any solid men’s wardrobe.
T-Shirts: Essential Basics
Every man needs a selection of plain t-shirts in neutral colors.
Neutral colors, such as black, white, grey, navy, and olive, are incredibly versatile and easy to combine. Bright, vibrant colors can be harder to coordinate and often give off a more youthful or less mature vibe.
Opt for crew neck t-shirts with a relaxed fit, like the A&F Essential Tees. Having multiple black and white tees is particularly useful, as they are incredibly versatile, especially for layering. Consider adding long-sleeve versions for cooler weather.
Graphic tees should be chosen sparingly and with subtlety. If you choose to wear one, look for designs with an artistic feel or understated graphics. Avoid ironic or overly humorous text, which can appear juvenile. Large logos or graphics with many colors outside your neutral palette should also be avoided for a more refined look.
Button-Up Shirts: Elevating Your Style
While t-shirts are suitable for casual settings and warm weather, button-up shirts can instantly elevate your style, offering a more sophisticated look.
For a step up in style, layer a button-up shirt over a t-shirt. Depending on the occasion and weather, you can choose between short-sleeve and long-sleeve options. Leave them unbuttoned to showcase the layers underneath.
Consider these versatile button-up shirt styles:
- Denim shirts
- Flannel shirts
- Solid color and textured shirts (oxford, poplin)
- Patterned and untextured shirts (gingham, stripes)
Sweaters and Sweatshirts: Versatile Mid-Layers
Sweaters and sweatshirts are excellent layering pieces that can be worn alone, over a t-shirt, or under a button-up shirt for added warmth and style.
Essential sweater and sweatshirt styles include:
- Crew neck sweaters in solid colors
- Knit and textured sweaters (cable knit, ribbed)
- Quarter-zip sweatshirts in neutral colors like gray or black
Jackets and Hoodies: Essential Outerwear
Jackets and hoodies are outerwear pieces that are always worn over another top, so versatility is key. Stick to basic colors such as black, gray, denim, or brown leather to ensure they complement a wide range of outfits.
Universal and timeless jacket styles include:
- Bomber jackets
- Trucker jackets (denim or corduroy)
- Utility jackets
- Plain pullover or zip-up hoodies
Pants: Building Your Bottom Half
Finding the right pants can sometimes be challenging. The key is to keep it simple and avoid overthinking.
Jeans: Wardrobe Staples
Every man should own jeans in three essential colors:
- Black jeans
- Dark blue jeans
- Light blue jeans
Opt for straight or straight slim fit jeans, such as the A&F 90s Straight Jean or Athletic Slim Jean. Avoid overly slim, bootcut, or loose fits, as these can easily look dated. Trust this advice for a timeless style.
Depending on your leg length, you might need to cuff the hem of your jeans so they fall correctly on your shoes. The ideal length is for the jeans to just reach the top of your shoes, creating a slight crease.
Chinos: Adding Variety and Texture
Chinos are another excellent pant option to add to your wardrobe, offering a different texture and color palette compared to jeans.
Essential chino colors include:
- Khaki chinos
- Olive chinos
- Navy chinos
Chinos can be slightly slimmer fitting if preferred, but a straight or slim-straight fit is also versatile and classic.
Shorts: Warm Weather Essentials
For shorts, a universally flattering style is “seersucker” in essential neutral colors.
Recommended seersucker short colors:
- Khaki seersucker shorts
- Gray seersucker shorts
- Navy seersucker shorts
The key to wearing shorts well is to choose the right length. Avoid shorts that are too long or too short. A good rule of thumb is for shorts to end just above the knee. This typically corresponds to an inseam of 7-9 inches, but you can adjust slightly based on personal preference.
Shoes: The Foundation of Every Outfit
Shoes can make or break an outfit. Even if the rest of your outfit is well-put-together, the wrong shoes can detract from your overall look. Conversely, a great shoe choice can elevate an otherwise simple outfit.
Shoes are also the easiest way to adjust the formality of your outfit.
You can build a versatile shoe collection with just three essential pairs:
- White sneakers
- Brown boots
- Sandals
Let’s explore each of these options.
Sneakers: The Universal Shoe
It might seem too simple, but white sneakers truly go with almost everything. They pair well with any color, texture, and style of clothing, from jeans to shorts, t-shirts to button-ups.
When in doubt, white sneakers are always a solid choice.
For a classic and versatile option, choose low-top leather white sneakers.
For added versatility, consider sneakers in all black or black and white. If you want to add a subtle twist, sneakers with rubber gum soles are also a stylish option.
Boots: Rugged and Refined
Boots can be tricky to get right. If they’re too rugged, they can look like work boots. If they’re too dressy, they might clash with casual outfits.
For leather boots, stick to rugged dark brown or black. For suede boots, opt for beige or chocolate brown.
Three reliable boot styles are:
- Chelsea boots
- Chukka boots
- Cap-toe boots
Sandals: Casual Comfort
Flip-flops are suitable for the beach, and slides are fine for home. However, neither are ideal for going out in public in most casual settings.
Birkenstocks are a stylish sandal option that pairs well with casual tops and bottoms. Suede or leather Birkenstocks elevate them beyond typical casual sandals.
Please, avoid wearing socks with sandals. While comfortable, it’s generally considered a fashion faux pas.
Accessories: Adding Personal Touches
Accessories are a great way to enhance your style, but it’s easy to overdo it. While some fashion experts advocate for multiple jewelry pieces and bags, a more minimalist approach to men’s accessories can often be more effective. Excessive jewelry or certain types of bags can sometimes appear overly feminine to some.
Three essential accessories for men are:
- Hats
- Watches
- Sunglasses
Hats: Classic Headwear
Sticking with the theme of timeless style, baseball caps are the most versatile hat style. They don’t fluctuate in and out of fashion like many other hat types.
Snapbacks, fedoras, truckers, cowboy hats, etc., are associated with specific looks and can easily become dated. Some, like fedoras, are often considered universally unflattering.
A baseball cap in a neutral color is a safe and stylish choice.
To add a bit of personal style, consider a baseball cap with your favorite sports team logo or a distressed twill dad hat.
Watches: Timeless Timepieces
Watch enthusiasts might have more specific recommendations, but for the average man who wants to subtly enhance his outfit, simplicity is key. You don’t need to spend a fortune to own a stylish watch.
Four essential watch styles that are versatile enough for most outfits include:
- Casio watches (many models offer a retro-cool vibe)
- A watch with a black face
- A watch with a white face
- A watch with a silver or gold band
Affordable and stylish watch options are available from brands like MVMT. For higher-end options, consider Swiss brands like Tissot or Seiko.
Smartwatches from brands like Apple, Samsung, Google Pixel, Fitbit, and Garmin are also great choices, especially when paired with upgraded straps and tasteful watch faces.
Any watch is generally better than no watch, adding a touch of sophistication to your look.
Sunglasses: Eye Protection with Style
Sunglasses are an important accessory, but choosing the wrong style can negatively impact your overall look.
Aviator, sport, and biker sunglasses, similar to fedoras and cowboy hats, don’t always stand the test of time in terms of style.
While certain sunglasses styles flatter specific face shapes, these two styles are generally universally flattering:
- Wayfarer sunglasses
- Clubmaster sunglasses
Affordable replicas of these classic styles are widely available, making them accessible to everyone.
Statement Pieces: Injecting Personality
Once you have a solid foundation of essential, versatile pieces, you can start incorporating statement pieces. These are items that don’t necessarily mix and match easily but add personality and individuality to your wardrobe.
Statement pieces often become the focal point of an outfit and should be paired with more understated, subtle basics.
Statement pieces aren’t necessarily trendy; they are often timeless in their own right but are bolder or more unique.
Examples of statement pieces include:
- A distressed oversized denim jacket
- A shirt or sweater in a vibrant color like orange, red, or light blue
- Vintage band t-shirts
- Camo pants
- Cargo pants
- Ripped jeans
- Black leather jacket
- Puffer vest
Putting It All Together: Outfit Examples
Here are a few simple outfit examples using the principles discussed, showcasing both warm and cool weather combinations.
These examples demonstrate versatile outfits for various weather conditions.
For reference, the model is 6’2″ and 200lbs with an athletic build, illustrating how these styles can work for different body types. Notice the relaxed fit of the clothing; while not overly baggy, a comfortable, relaxed fit from top to bottom helps maintain balanced proportions.
Inspiration for Developing Your Style
For further inspiration and more detailed style advice, check out these highly recommended YouTube channels focused on men’s fashion: (You can insert specific channel names here if desired, but they were not in the original article).
If you’re still feeling unsure, remember these core basics:
- Solid neutral colored shirts
- Straight fit jeans
- White sneakers
With these essentials, you’re well on your way to dressing better and feeling more confident in your style. You’ll definitely avoid looking outdated, and instead, you’ll project a timeless, stylish image.
