“Dressing well is a form of good manners.”

– Tom Ford

There comes a time in every man’s life when he looks at his wardrobe and wonders why he owns a dozen graphic T-shirts but not a single decent pair of shoes. Maybe it happens when he’s invited to a wedding and realizes his best option is an old blazer from college. Maybe it’s when he catches his reflection in a shop window and sees a man who looks more like a lost teenager than someone in control of his life. Either way, it’s a moment of reckoning.

A classic wardrobe isn’t about fashion. It’s about having the right tools for the job—much like a well-stocked toolbox. You wouldn’t fix a leaking pipe with a butter knife, so why show up to a meeting in a hoodie? The goal is to build a collection of clothes that work in every situation, require minimal thought, and get better with age—like a good leather wallet or a well-made whisky.

Here’s the trick—fit is everything. You need clothes that actually fit your body. No, those baggy jeans and ill-fitting suits aren’t doing you any favors. Find a tailor. Yes, it’s a pain, and no, you’re not too tough for it. A good tailor is like a secret weapon in your closet—once you’ve had those items tailored, you’ll never want to go back. And your clothes will actually look like they belong on you, not like you borrowed them from your older brother.

The Foundations: Get the Basics Right

Before you even think about pocket squares, let’s start with the essentials. These are the garments that should always be in your arsenal. If you own them, you’ll never be the guy frantically googling ‘what to wear to a funeral’ the morning of.

1. The Navy Blazer

This is your Swiss Army knife. It works with everything. Wear it with jeans, wear it with chinos, wear it with dress trousers. Get one in a classic cut with notch lapels and natural shoulders. If it has gold buttons, you better have a yacht. Otherwise, stick to dark buttons.

Brooks Brothers Blazer

2. The White Oxford Shirt

There’s a reason every serious man owns one. It works for business, dates, weekends, and everything in between. Wear it crisp with a blazer or rumpled with rolled sleeves. Either way, you look like a man who knows what he’s doing.

Brooks Brothers Oxford Shirt

3. Brown Leather Shoes

A man’s shoes say everything. Beat-up sneakers tell the world you’ve given up. Polished leather Oxfords or Loafers say you’re someone who takes care of details. Brown is more versatile than black—unless you’re attending royal funerals regularly.

Ralph Lauren Penny Loafers

The Refinements: Elevating Your Style

Once you’ve secured the essentials, you can start refining. This isn’t about peacocking—it’s about having options that quietly set you apart.

1. A Proper Coat

If you’re still relying on your high school windbreaker, it’s time to upgrade. A classic wool overcoat in navy, grey, or camel works over a suit or a sweater. It makes you look like a man, not a boy trying to avoid the cold.

Cole Haan Top Coat

2. The Well-Fitted Suit

At some point, you’ll need a suit. When you do, make it navy or charcoal. Single-breasted, notch lapel, two-button. Get it tailored—yes, tailored. An off-the-rack suit that fits perfectly is as rare as an honest politician.

Brioni Men's Twill Wool Suit

3. A Mechanical Watch

Your phone tells the time. Your watch tells a story. It doesn’t need to be a Rolex, but it should be mechanical. Quartz is fine for microwaves, not your wrist.

Hamilton Field Watch

The Mindset: Dress Like a Gentleman, Not a Trend

A timeless wardrobe is about dressing in a way that respects yourself and the people around you. Think of the old-school gentlemen—the ones who didn’t spend hours agonizing over outfits, but still looked put together.

Here’s the secret: They had fewer clothes, but better ones. They knew what worked for them. They understood that looking good isn’t about showing off—it’s about showing up prepared.

So build your wardrobe like you build your life: with intention, discipline, and a healthy dose of common sense. Buy things that last. Wear them with confidence. And for the love of all that is good, stop wearing flip-flops to dinner.