Gents Weekly: Dress for Success and Gain Looks that Impress
Issue #16: The manliest newsletter on the internet • April 27, 2026
Welcome to issue #16 of The Gents Weekly, a newsletter for the modern man.
Every Monday, you’ll receive a weekly roundup of inspiring ideas + products to help you become a better man.
Brought to you by the men of Gents Journey — Dean Bokhari, Stephen Seidel, and Matt McManus.
ANNOUNCING
The Gents Weekly Podcast
The manliest podcast on the internet.
Listen & subscribe on
Substack | Apple Podcasts | Spotify
📝 THE MESSAGE
A timely piece from the gents.
↓
10 tips to become a more presentable man
There’s a trend happening on the internet right now.
It’s called “looksmaxxing.”
Looksmaxxing • noun | LOOKS-mak-sing
An online self-improvement practice, primarily practiced amongst men, that is focused on the process of maximizing one’s own physical attractiveness.
In today’s issue, we’re going to be looking at a few simple things you can do to “max-out” your own looks.
Here are 10 ideas to get you started:
Define your jawline with facial exercises. My favorite is the “jaw chin up”. Here’s how to do it:
With your mouth closed, push your lower jaw out and lift your lower lip.
You should feel a stretch build just under the chin and in the jawline.
Hold the position for 10 to 15 seconds, then relax.
Perform 3 sets of 15.
Get a tan. When it comes to putting your best foot forward, a nice tan goes a long way. Get some sunless tanner and put it around your cheek bones and jawline to accentuate both. Tan your body to give your muscles a bit more definition.
Wear clothes that fit properly. This alone can be a complete game changer if you’re not sartorially inclined. Lose the baggy jeans and oversized shirts. Look for pants that fit properly (look for “slim fit” or “tailored” fits). Get t-shirts that hug your biceps. Have your suits tailored.
Exercise. Lift weights for muscle gains at least three days a week. Incinerate those love handles with 20–40 minutes of moderate-intensity cardio at least three days a week.
Moisturize. Putting lotion on your skin isn’t gay or girly. It’s healthy. Grab yourself a bottle of unscented Kiehl’s and go HAM. If you’re looking for a low-budget option: use a bit of organic unrefined cold-pressed coconut oil.
Wear quality shoes. Your shoes are one of the first things women notice about you. And that shitty old pair of cracked leather loafers ain’t gonna cut it. At an absolute minimum, you need three types of shoes: a pair of training shoes for the gym, a sophisticated pair of casual shoes, and a sharp pair of dress shoes. My top picks:
Stay hydrated. Drink enough water every day. Hydration reduces puffiness and helps flush out toxins that can cause your face to look bloated and chubby. A toxin-free system reflects in the face, making it look slimmer and clearer.
Keep a light beard. Stop shaving your face completely and keep a crisp-looking 5-o’clock shadow instead. Here’s how: Use an electric razor to maintain a bit of stubble. Shave your neckline to make your jawline pop. Keep the top of your beardline neat by lining it up with a regular razorblade.
Get rid of those dark circles with a quality under eye cream.
Eat well. Have a well-balanced diet with plenty of protein, healthy fats, complex carbs, and lots of green leafy vegetables. Eating clean whole foods will show in your appearance. Use Athletic Greens to fill any nutrition gaps.
— Dean Bokhari
Co-founder, Gents Journey
Share this with a friend who could use it.
📰 THE MOMENT
Sh*t that’s happening now, ICYMI
↓
This Week’s AI Prompt: Dress for Success
What would happen if you dressed like you already made it?
Here’s the truth: most guys dress like they don’t give a shit.
Not because they don’t care. But because at some point, “dressing well” felt like it was for other people. Like trying too hard. Like something you do when you’re trying to impress someone, not when you’re just living your life.
But how you dress changes how you show up. It changes how people treat you. It changes how you treat yourself.
You don’t need a stylist or a huge budget. You just need to stop wearing clothes that don’t fit, shoes you’re embarrassed by, and the same hoodie you’ve had since 2015.
This prompt helps you figure out how to dress like the man you’re trying to become—without overthinking it or turning into the guy who owns 47 pairs of sneakers.
THE PROMPT:
Copy everything below and paste it into ChatGPT or Claude:
I want to upgrade how I dress so I look like I have my shit together—without trying too hard or spending a fortune.
Help me:
1. Audit my current wardrobe honestly
- What do I wear most often? (Be real—not what's hanging in the closet, what I actually wear)
- How do I feel when I get dressed? Confident? Indifferent? Like I'm just grabbing whatever's clean?
- What clothes do I own that I feel great in vs. clothes I'm just tolerating?
- What's one thing I wear that I know I should replace but keep putting off?
2. Define what "dress for success" means to me
- What does success look like in my life? (Not a suit if I work from home, not joggers if I'm in client meetings)
- Who's a guy I see and think, "That dude looks sharp"? What is it about how he dresses?
- What's my context? (Office job, creative field, entrepreneur, stay-at-home dad, etc.)
- What do I want people to think when they see me? (Put together, confident, approachable, professional, creative?)
3. Identify what's holding me back
- Is it money? Not knowing where to shop? Thinking "it doesn't matter"?
- Am I wearing clothes that don't fit because I'm waiting to lose weight?
- Am I telling myself I'm "too old" or "too casual" to care about this?
4. Build a simple wardrobe upgrade plan
- What are the 5-7 core pieces every guy needs that work for my life? (Jeans that fit, clean shoes, a jacket, etc.)
- What's ONE thing I could buy or upgrade this week that would make the biggest difference?
- What's ONE thing I need to throw out or donate because it's not serving me anymore?
5. Create my "Dress for Success" rules
- What does my daily uniform look like when I'm showing up at my best?
- How do I make getting dressed effortless but intentional?
- What's my go-to outfit when I need to feel sharp?
Here's what my wardrobe looks like right now: [Describe what you wear daily]
Here's what success looks like in my life: [Describe your work/lifestyle context]
Don't let me overcomplicate this. Give me simple, actionable upgrades that fit my life and budget.
WHAT HAPPENS NEXT
The AI is going to help you build a wardrobe that fits your actual life—not some fantasy version of yourself.
By the end, you’ll have:
A clear audit of what’s working and what’s not
A list of core pieces you actually need
One upgrade you can make this week
Simple rules to make getting dressed effortless
WHY THIS MATTERS
How you dress is how you show up.
When you wear clothes that fit, shoes you’re proud of, and put even minimal effort into how you look, you walk into rooms differently. You handle meetings differently. You respect yourself differently.
This isn’t about becoming someone you’re not. It’s about looking like the version of yourself you’re trying to become.
You don’t need a huge budget. You don’t need to follow trends. You just need to stop settling for “good enough” and start dressing like you give a shit.
Run this prompt. Upgrade your wardrobe. Show up sharper.
Drop one thing you’re going to upgrade or throw out this week. Let’s see who shows up looking like they mean business.
— Matt McManus
Co-founder, Gents Journey
Dress Like You Already Made It
👊 THE MOVES
Media for men.
↓
Watch | How to Tie a Double Windsor Knot
Be sure to subscribe to our Gents Journey YouTube channel
(Watch the video above first.)
The Mirror Doesn’t Lie
There's a scene I come back to often. I'm standing in my bathroom before a big meeting — tie on, shoes shined — and I look in the mirror and think: Yeah. I'm ready.
Watch the video above on how to tie a Double Windsor knot. My stepdad, Tom, taught me that one.
He said the simple Windsor was fine, but the double showed class and character. He was right. And I still think about him every time I pull that knot tight.
The Double Windsor knot is two loops instead of one, creating a thick, symmetrical triangle that sits perfectly in your collar. It takes an extra thirty seconds and signals something most guys never bother to — that the details matter.
Top 10 and Lower 10
Too many guys spend energy worrying about what others think instead of focusing on how they feel about themselves.
And here’s the thing — confidence is visible. Women will tell you that unprompted.
In college, my roommate and I had a simple system: the Top 10 and the Lower 10. Think of it as Pareto’s Law applied to your appearance. The 20% that makes 80% of the impression.
The Top 10 is everything from your neck up — your hair, your smile, your eyes, and yes, your tie. Get a haircut every four to six weeks. Make eye contact. Smile like you mean it. These aren’t small things. They’re the things people remember.
The Lower 10 is your shoes. Shine them. Replace the insoles before a big meeting. And if you’re wearing Crocs anywhere outside the four walls of your own home, we need to have a different conversation.
Here’s a question from our Journey Deck: What gifts do you give yourself to look and feel your best?
Invest In Yourself
Today, stand in front of a mirror and do an honest audit of your Top 10 and Lower 10.
Pick one thing and do something about it. A haircut. A new tie for your meeting.
A fresh pair of Johnston & Murphy’s — they look like dress shoes and feel like running shoes, best of both worlds.
Then, before you walk into that room, look in the mirror and say it out loud: “I look good, damnit.”
Here’s your one takeaway: when you invest in how you show up, you show up differently.
You are the Top 10%. It’s time to start dressing like it.
If you have any other suggestions on tips or tricks to look and feel amazing, drop in the comments below.
Together we raise each other higher!
— Stephen Seidel
Co-founder, Gents Journey
🔗 MEANINGFUL MENTIONS + MAGIC LINKS
Fun stuff you’ll dig about our theme of the week.
↓
💻 REAL MEN HAVE A COACH IN THEIR CORNER
Stop playing small, step into the man you know you are.
_
We’re looking for ten men who want coaching and guidance to level up in life + work. If that’s you, fill out this form, and we’ll be in touch.
Until next week,
—The Gents
Inspired? Share this newsletter with another Gent you think it could help.