Bossa On Sundays

Bossa On Sundays

10 Easy Ways To Always Look Your Best

From a conversation that started on IG this time last week to the pages of your favorite Stack.

Darren Griffin's avatar
Darren Griffin
Aug 31, 2025
∙ Paid

I’ll never understood the fascination with trying to look rich when you’re far from rich. Layering piles of labels upon labels to Gucci/Balenci/Prada onlookers into a wealth-induced coma. And for what? Knowing good and well your rent is past due, the credit cards are beyond maxed, and you’re returning those clothes first chance you get.

It’s an all too familiar story of consumers wildly stretching themselves to tap into luxury culture before their budget actually allows.

Where is all this coming from? Well, last week a friend sent me an article from an online menswear retailer that offered secrets to looking more expensive. I guess he assumed I would either be interested or have an opinion to share.

Neither notion was a complete affront; but I certainly wasn’t interested in the article itself. I was, however, interested in offering a rebuttal in the form of how men can…not necessarily look expensive, but define a method in which they can always look their best.

I put together a list of ten simple ways in which men can look good without trying too hard. Or just buying expensive clothes to compensation for a lack of refinement. So, in no real order, let’s get into it.

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