Why A Good Tailor Might Be The Best Style Investment You’ll Ever Make

There’s a lot of talk about quiet luxury as a trend — pieces that whisper rather than shout, signaling their value through craftsmanship, not logos. But the real power of clothing isn’t just about cost. It lies in proportion, intention, and the way a garment drapes when it’s made (or remade) to fit you perfectly. It’s something that reveals itself in motion.

Perfect fit, however, rarely exists straight off the rack. And that’s where a good tailor becomes indispensable. The secret architects of personal style, they can transform a piece of clothing from something you simply wear into something that feels like a second skin.

“When an item truly fits, you carry yourself differently,” says Chandler Guttersen, founder and curator of Vintage Grace. That’s why the industry’s most fashion-minded people — designers, stylists, editors — treat a trusted tailor as non-negotiable. It’s one of the smartest style investments you can make: extending the life of your clothes while elevating how you feel in them.

Here, Guttersen, along with textile artist Sarah Nsikak and designer Patricia Voto of One/Of, reminds us that tailoring doesn’t just fix clothes — it redefines your relationship with them.

Fit Is Everything

“A fine tailor doesn’t alter a garment; they reconcile it to the person who wears it,” says Voto. “That alignment is what makes clothing feel effortless and perfectly suited for its wearer.” It’s a simple truth that’s easy to forget in a trend-driven world: fit is the ultimate luxury.

Make Pieces Feel More “You”

Instead of discarding a piece that isn’t quite right, Nsikak suggest reimagining it. “I have a vintage silk shirt that I never wore until I cut and hemmed the sleeves because I didn't like where they hit,” she says. “I gave them a bit of an angle because I know that shape flatters me, based on my other shirts that I actually wear.” Fit alterations are one thing, but a tailor’s real superpower, she adds, is addressing the nuances of you. It’s less about a garment being wrong, and more about shaping it to your own proportions, preferences, and personality.

Learn What You Love

Quality tailoring, Nsikak emphasizes, is a process that require patience. “You might not find the perfect tailor on the first try, but it’s never a waste — every experience helps you develop the language to describe how you want your clothes to feel on your body, which is deeply personal.” Like any meaningful relationship, it’s built on respect and trust.

Connect The Past and Present

For Guttersen, tailoring is not about changing the soul of a piece, but giving it a new life. It can be particularly useful for vintage clothing, which oftentimes have different sizing from modern clothing. “Tailoring breathes new energy into vintage and gives you a sense of individuality and polish that trends can never replicate,” she says. “It connects past and present in the most personal way.”

She recalls one of her most meaningful transformations: “My tailor transformed a vintage Gianni Versace blazer that belonged to my father into a mini dress without losing an ounce of the original magic,” she shares. “It still feels like his jacket — with all its history and presence — but now it fits my body and my world. That is the power and poetry of tailoring.”