How to Dress Like Money

Dressing like money isn’t always about wearing the most expensive brands head to toe. It’s about putting together a look that feels intentional, polished, and timeless — even when the pieces themselves are simple. For Saturday’s date night, I leaned into an elevated casual outfit that shows how to strike the right balance between laid-back comfort and quiet luxury.

1. Start with a Clean Base

A crisp white T-shirt is the ultimate foundation. Mine is from Banana Republic, but the brand isn’t the focus — it’s about fit and quality. A well-made tee instantly separates your look from casual basics that feel thrown together. Think of it as the blank canvas that sets the tone for the rest of the outfit.

2. Add Subtle Luxury

Accessories are what give an outfit that “rich” edge. I went with Saint Laurent shades, which add sophistication without being flashy. The lesson here: invest in one or two strong accessories that can elevate even the simplest look. The right pair of sunglasses, a clean watch, or even a sharp belt can carry an entire fit.

3. Upgrade Your Textures

Instead of defaulting to jeans, I chose faux leather pants. Texture is an easy way to make your outfit look expensive — leather (even faux) instantly adds depth and polish. These pants keep things modern and sleek without pushing into overdressed territory.

4. Anchor with Classics

On my feet, I finished the look with Air Jordan Bred 1s. Jordans are iconic, and this pair in particular balances heritage and style. They ground the outfit with a sense of culture and timelessness. Dressing like money isn’t always about a dress shoe or a loafer — it’s about choosing footwear that feels intentional and holds weight in its own lane.

5. Keep It Effortless

The secret to dressing like money is confidence without overcomplication. Each piece here is simple, but when combined, they create an elevated casual look that feels sophisticated without trying too hard. For guys who don’t enjoy “dressing up,” this is a formula that delivers polish, comfort, and presence all at once.

Takeaway:

To dress like money, think in terms of formula: clean base + subtle luxury + elevated texture + timeless sneakers. Keep the outfit simple, let each piece carry its weight, and focus on details that feel intentional. That’s how you project wealth and confidence without saying a word.