👖 High Fives, Hard Truths, and Dark Wash Jeans

Hey Reader,

It's the first Saturday of the month and as promised, I've got a new edition and refresh of Gent Within's weekend newsletter (#79) centered around some of my favorite topics.

Once a month, we’ll cut through the noise with ideas to sharpen your style, fuel your growth, and keep your compass pointed toward the life you actually want to live.

Let's dive in!

In today's S'letter:

• Style: How to Wear Dark Wash Jeans (3 Easy Ways)
• Life: Lean Into Resistance
• Relationships: The Science of the High Five
• Earn: When "No" is the Kindest Answer
• Worth Pondering: Antelope or Mice?

STYLE

3️⃣ Easy Ways to Wear Dark Wash Denim

Why is dark wash denim considered a men’s style essential? Mainly because of its versatility, durability and timelessness.

It serves as the anchor for a myriad of outfit combinations. Unlike the light wash variety, you can dress dark wash jeans down with a t-shirt or dress it up with a navy blazer.

It’s also appropriate for more casual workplaces and after work happy hours. Maybe you have an exciting date coming up? Dark wash jeans is always a smart choice.

Here are 3 scenarios that you can rock this fall staple:

👖 Scenario #1: The casual weekender

Whether you’re running errands, off to school or meeting up with buddies for drinks – dark blue jeans can serve you well.

This simple look is casual from the top down. The gray check flannel shirt is inherently casual. There's a rounded ‘club’ collar which gives it a unique flair.

Pair a similar shirt with a light quilted vest suede desert boots, and dark jeans – you’ve got a rugged, yet still refined combo.

The Timex Weekender watch with a casual leather strap completes this simple getup.

👖 Scenario #2: The smart casual office space

Find yourself in a more casual work environment? This smart casual outfit works well in the office.

The shawl neck sweater is a casual piece that ventures into rugged territory depending on what you pair it with.

In this case, the addition of a white oxford button-down shirt helps to increase the level of formality a tiny bit. And a clean pair of suede chukkas, in navy keeps the look balanced with earth tones, of dark blues and the teal of the cardigan.

You’ll look on point style wise with this simple getup, topped off with a minimalist brown leather watch to match the belt.

👖 Scenario #3: The date night

So it’s date night with your special lady?

Here’s how you can dress up dark wash denim.

In this scenario, I'm elevating our trusty dark blue jeans with a silk blended charcoal blazer that ups the classy vibe. The silk blend gives off an air of elegance that is perfect for a fancy date or anniversary.

I paired a light blue bengal striped shirt with a navy, speckled tie that's made of a wool fabric, contrasting nicely against the lighter shirt. Don’t be afraid to mix patterns and textures.

A pair of brown brogues like that of Allen Edmonds (formerly the Strand in Walnut) always looks great with dark jeans. You can of course go darker with your shoe shade according to your personal taste.

GW S'LETTER SPONSOR

LIFE

🌱 Lean Into Resistance

Steven Pressfield calls it Resistance in his classic The War of Art. (This book helped me break thru the resistance holding me back from starting Gent Within). It’s that invisible force that shows up whenever we try to do something meaningful – write the book, start the business, finally get in shape.

He explains it through The Hero’s Journey. Think Luke Skywalker stuck on Tatooine. The call to adventure comes, but Resistance is strongest right before he says yes. Why? Because the stakes are high. Saying yes means growth, change, responsibility.

Pressfield puts it bluntly: “The more important a call or action to our soul’s evolution, the more Resistance we will feel toward pursuing it.”

Here’s the paradox – the thing you fear the most, the thing you keep putting off, is likely the exact thing you must do.

👉 In real life, Resistance might look like this:

• You’ve wanted to start a YouTube channel but keep telling yourself “I’m not ready.”
• You want to run a 10K but keep putting off the first training session.
• You’ve been meaning to have that tough conversation but keep waiting for the “right moment.”

This week: Notice where Resistance shows up. That’s your Tatooine moment. Step off the farm. Answer the call.

RELATIONSHIPS

🙌 The Science of the High Five

Ever notice how a simple high five can flip your mood? Turns out, it’s not just playground nostalgia. There’s legit science behind it.

1. Instant Dopamine Hit

Physical gestures like high fives, fist bumps, or hugs trigger the release of dopamine and oxytocin – the “feel-good” chemicals. Translation: it's basically a micro-dose of motivation.

2. Performance Booster

A study out of UC Berkeley found that NBA teams who celebrated with high fives, chest bumps, and fist bumps early in the season went on to win more games. Why? These small, positive cues built trust, connection, and team cohesion. The same applies at work or in relationships. Celebrating tiny wins together adds up.

3. Stress Down, Confidence Up

Non-verbal cues communicate safety and support faster than words. A reassuring pat on the back or clasp of the shoulder lowers cortisol (your stress hormone) and raises feelings of belonging. It’s biology’s way of saying, “You’ve got backup.”

How to Apply It

• At work: Celebrate progress, not just results. High five your team after a presentation. Yes, even on Zoom (camera high fives work).
• In relationships: Don’t underestimate the casual shoulder squeeze, hand on the back, or hug. It signals presence and builds intimacy without words.
• For yourself: High five the mirror. Sounds goofy, but research from author Mel Robbins shows it boosts self-compassion and primes your brain to see yourself as an ally, not a critic.

Bottom line: non-verbal gestures are free, quick, and ridiculously effective. Use them daily. High five your partner, fist bump your coworker, hug your friend. You’ll lift them up, and yourself in the process.

EARN

💸 When “No” is the Kindest Answer

Family makes it tricky. You want to help, but sometimes “help” is really just enabling.

Recently, a relative reached out saying she was sick and needed money. She promised she’d pay me back… the same promise she made the last time, and the time before that. Truth is, she never asks how I’m doing. The only time I hear from her is when she needs cash.

I’ve given before, not expecting to see the money again, but this time I realized what was really happening. I wasn’t helping her – I was fueling the cycle. By saying yes, I was making myself “easy money.” And once people see you that way, they never stop asking.

Jay-Z once said he declined a cousin who asked him for seed money to start a business. This is a man worth over a billion Even he knew that money doesn’t fix habits. It doesn’t create discipline. And many wealthy parents take the same stance with their kids. They refuse to hand them fortunes because they know that unearned money often destroys more than it builds.

The truth is simple: generosity needs boundaries. If someone truly values you, their relationship with you won’t hinge on your wallet. Sometimes the most loving answer, the one that actually helps, is “no.”

👉 Next time guilt comes knocking, remember: you’re not being cruel. You’re setting both of you free.

💭 Worth Pondering

I recall a Tim Ferriss podcast episode where he tells a story of the lion that can hunt either antelope or field mice. Catching mice is easy, but they don’t provide enough energy to survive. Antelope take more effort, but they fuel the lion for days.

Most of us waste energy chasing mice, (busywork, distractions, low-value tasks) instead of focusing on the antelope, the high-impact moves that actually change our lives.

👉 This month: ask yourself, am I hunting mice or antelope?​​

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