Lately, I’ve been diving into Discipline Is Destiny by Ryan Holiday—a book that’s all about self-mastery, habits, and, as the title suggests, discipline. There’s this short but solid chapter on dressing for success that really stood out to me. It got me thinking: why do we put so much emphasis on what we wear? Is it just vanity, or is there something deeper at play?
If you’re in your 20s, like me, and figuring out your career, social life, and overall identity, the way you present yourself matters. A lot. Whether you’re walking into a client meeting, heading out on a date, or just grabbing a coffee in Soho, your outfit is a signal. It tells people who you are before you even open your mouth.
First Impressions Are Everything
Like it or not, we live in a world where people judge books by their covers. I’m not saying you need to be in a full Tom Ford suit at all times (although, fair play if you are), but putting effort into your style shows you respect yourself—and the people around you. It’s a form of self-discipline, and as Holiday suggests, discipline in small things builds discipline in bigger things.
It’s About Confidence, Not Just Clothes
You ever put on a well-fitted blazer and instantly feel like you could negotiate a deal, land a job, or chat up that girl across the bar? That’s not a coincidence. Dressing well makes you feel like you belong in any room you step into. And when you feel good, you carry yourself differently—shoulders back, chin up, energy on point.
Know Your Personal Uniform
Steve Jobs had his black turtleneck. Daniel Craig’s Bond had his tailored suits. You don’t need a stylist to figure out what works for you—just experiment until you land on a signature look that fits your personality and lifestyle. My go-to? Black Tailored trousers, a knitted sweater of fitted tee and then a clean sneaker or loafer. Works for business meetings, date nights, and everything in between.
Invest in Quality, Not Quantity
One of the biggest style mistakes guys in their 20s make is buying loads of cheap, trend-driven clothes. Fast fashion is tempting, I get it—but it’s far better to have a few high-quality essentials than a wardrobe full of stuff that falls apart after three washes. A solid wool coat, well-structured jeans, a pair of leather loafers—these are the pieces that’ll last and elevate any look.
Final Thoughts
Dressing for success isn’t about trying to impress people—it’s about setting a standard for yourself. It’s about discipline, self-respect, and showing up as the best version of yourself every day. So next time you’re getting dressed, ask yourself: Am I putting my best foot forward?
Because trust me, people notice. And more importantly, you’ll notice the difference too.
Your pal, Taylor.
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