How to Style an Oversized T-Shirt Like a Rich Guy
In a world where fashion speaks louder than words, one quote says it all:
“We Don’t Chase, We Attract.”
It's your energy, not simply your attitude. And that energy turns into a statement of power when it is printed on an opulent, oversized T-shirt. The challenge is, though, how to style it like the TikTok starboys who exude confidence, the wealthy men, and the airport suits.
Using Alex Shogun's iconic piece as the focal point, here's your comprehensive guide to decorating giant tees with a contemporary edge and old money taste.
5 Stylish Outfit Ideas with an Oversized T-shirt:
1. ✈️ The Airport Outfit: Effortless Wealth
This is the classic rich-but-lowkey look. The kind of fit that says, “I fly private, not flashy.”
Wear it like this:
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Oversized T-shirt (black, grey, or navy)
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Wide-leg linen or jersey pants
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Clean designer sneakers (think white leather or subtle runners)
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Additional, a soft minimalistic design hoodie or a leather bomber jacket
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Dark sunglasses + a travel tote
👉 Optional: Add a gold chain or a luxury watch peeking from the sleeve. Think Drake-meets-quiet luxury.
2. 🌒 The Asian Starboy Look: Sleek, Mysterious, Bold
Femme-meets-power energy is popular on TikTok and in Korean/Japanese streetwear design. It's more about mood than muscle. Ideal for a serious dating night or for the nightlife crowd. This ensemble is incredibly fashionable and appealing to women.
How to pull it off:
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Oversized T-shirt (tucked slightly in front) or Oversized Shirt
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Flowy or flared black trousers and jeans
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Chelsea boots or thick-soled loafers, sneakers
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Layered rings + chain + black sunglasses
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Leather jacket or oversized trench
💡 Hair and posture matter here. Keep it sharp, clean, and intentional.
3. 🏖 Old Money Summer: Linen Pants & Quiet Power
If you want to channel the vibe of a trust fund heir summering in Monaco, this look’s for you.
Go for:
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White, cream or navy oversized T-shirt (Can be oversized Shirt)
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Cream, beige linen trousers or striped blue pants (jeans)
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Brown loafers or minimalist sandals
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Brown leather belt + gold-toned or silver minimalistic watch
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Wavy hair, undone look, light cologne
🚶♂️Perfect for seaside strolls, café terraces, or luxury vacations. It’s old money meets relaxed masculinity.
4. 💼 Business-Casual Rebel: Breaking Rules with Confidence
Because real confidence is not about dressing like everyone else.
The formula:
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Oversized tee layered under a structured blazer
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Slim or straight-leg trousers
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Designer sneakers or loafers
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Small silver accessories for edge
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Black sunglasses + a leather crossbody or brief
🔥 This look is huge in Milan and Paris fashion weeks. The contrast between casual and tailored is the secret.
5. 🎥 The TikTok Rich Guy Fit: Flash Meets Discipline
Think of the guys pulling up in a matte black G-Wagon wearing all-black fits with confidence like a currency.
Style like this:
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Black oversized T-shirt (tucked slightly better with minimalistic text on back)
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Black cargo or tech pants, white baggy pants
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Chunky designer sneakers
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Iced-out accessories or watch
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Luxury cap or black shades
- Additional Expensive Car (Just a Joke)
📱 Perfect for reels, car shoots, city walk content, or that casual-but-flex TikTok scroll moment.
✨ Why This T-Shirt Works With Every Look
The “We Don’t Chase, We Attract” T-shirt isn’t just a fit — it’s a mindset in fabric.
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Oversized cut = relaxed confidence
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Minimalist design = high-end streetwear can also be used in luxury styles
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Statement quote = personal power
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Dark Creed Legacy aesthetic = part street, part heritage, all boldness
- Long-lasting = 100% organic combed ring-spun cotton—ultra-soft, breathable, and eco-friendly. The perfect balance of comfort and durability
It’s not about wearing a shirt. It’s about wearing a message — and letting the world catch up to your energy.
💭 Final Style Tips
✔ Oversized for relaxed, confident energy
✔ Statement quote that reflects mindset
✔ Neutral tones for luxury versatility
✔ Designed for the man who leads, not follows
Whether you're dressing for a flight, a date, or content creation, this tee delivers impact without effort.
Confidence is what you wear.
Make it your signature.
👉 Shop the “We Don’t Chase” Oversized T-Shirt
👉 Explore more luxury fits at Alex Shogun
Alex Shogun will improve your style and confidence!
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