Is Boston the Worst-Dressed City? A Stylist’s Perspective on Practicality, Style & Personal Expression
Why One Trip to Miami Shifted My Perspective on Boston Style
A few weeks ago, I spent time in Brickell, Miami—far from the flashy chaos of South Beach. What stood out wasn’t just the beautiful restaurants or local flair, but how everyone got dressed. Thoughtfully. Boldly. Elegantly. People of all ages embraced personal style with intention—from layered jewelry and tailored pieces to luxe fabrics that made dinner feel like a runway.
It sparked a question: Why don’t we see this same energy in Boston?
The Truth About Boston Fashion Culture
No shade to our beloved city, but let’s face it—Boston isn’t exactly known for its style. In fact, GQ once ranked Boston as the worst-dressed city in America. Function rules here. From weather-proof gear to the black tee + jeans uniform, we often save our most exciting outfits for trips elsewhere—New York, L.A., Miami—because we “could never wear that here.”
But why not?
It’s Not Laziness, It’s Lifestyle
Let’s be real: Boston living demands a lot. People are juggling careers, families, long commutes, and intense schedules. Between real estate, childcare, and dinners out, the mental load is heavy—and fashion becomes an afterthought.
That’s where the idea of intentional style comes in. Smart wardrobe planning isn’t about excess—it’s about ease, clarity, and showing up with confidence.
Why Personal Styling Is on the Rise
Across the country, we’re seeing a shift toward personalized styling and away from traditional retail. But in Boston? We’re late to the game. Many are still hesitant to invest in a stylist, fearing it feels “too much” or indulgent.
But here’s what I often find: I show up to a multimillion-dollar home, and inside is a closet filled with Amazon, Target, and J.Crew. It’s not about labels—it’s about alignment. Are you dressing in a way that reflects who you are and where you’re going?
The Future of Boston Fashion is Functional and Fly
Boston’s style scene is evolving. The tech boom, young professionals from bigger fashion cities, and a new wave of entrepreneurs are shifting the narrative. The desire for authenticity is rising—and that includes in our wardrobes.
People want to look polished, feel like themselves, and still move through life practically. That’s my sweet spot as a stylist: blending real-life demands with real self-expression.
You Don’t Need to Be Miami—Just Be Intentional
Boston may never be known for avant-garde street style, and that’s okay. We’re a walking city with unpredictable weather and real responsibilities. But that doesn’t mean fashion has to be boring or invisible.
My goal? Help you build a wardrobe that fits your life—practical, stylish, intentional. So when it’s time for dinner at the hottest new spot, you don’t default to a black tee and jeans. You wear something that makes you feel alive.
Ready for a wardrobe that actually works for your life? Book your styling appointment today!
xx Amanda
