What does it truly mean to look chic? While the term often conjures images of smart, sophisticated, and effortlessly put-together individuals, the practical details can be elusive. To demystify this coveted aesthetic, we asked a range of stylish professionals—from illustrators and makeup artists to organizers and content creators—to share the specific habits and details they find most chic. Their insights provide a masterclass in cultivating personal elegance.
Building a Foundation of Effortless Style
The consensus among experts is that chic often starts with a foundation of intentional choices rather than fleeting trends. Tevy Khou, an illustrator and art director, champions investing in high-quality, timeless staples over fast fashion. She highlights the importance of a well-fitted white T-shirt, indigo jeans, and leather Chelsea boots as versatile pieces that work for everyone.
This philosophy extends to fit. Iris Miyasaki, a home organizer and wardrobe stylist, insists that nothing is more chic than perfect tailoring. "Even affordable pieces can look elevated and expensive when they fit you properly," she notes, advising to make a habit of tailoring new wardrobe additions.
Several stylists emphasize the power of a personal uniform. Khou points out that a consistent formula, like an all-black ensemble or a specific combination like a Barbour jacket with trousers and boots, reads as confident and intentional. Similarly, Charlotte Upshaw, a professional organizer, admires those who lean into a particular silhouette that works for them, making getting dressed effortless.
The Power of Personal Expression and Details
True chic, however, transcends basics and enters the realm of personal expression. For Alexis Barber, a content creator, treating glasses like intentional jewelry—having multiple pairs to style with different outfits—adds depth and an unexpected edge.
Personal history and meaning also elevate style. Rachel Lovely, a content creator, finds it incredibly chic to incorporate pieces with history, like a borrowed heirloom or a handmade gift from a family member, into everyday wear. Caragh Donley, a TV producer and writer, offers a powerful perspective on personal rules. As a 66-year-old trans woman, she declares, "The main rule is there are no rules for me." Her approach is to wear what she's always wanted to, pushing limits and ignoring external expectations about age or appropriateness.
Small, thoughtful details repeatedly emerged as chic differentiators. Celebrity makeup artist Cat Mignano loves letting a tee peek out at the collar and hem under a sweater for added dimension. She also advocates skipping mascara with clean makeup and a bold lip for a modern, effortless feel. Chloe Xandria, a midsize fashion creator, swears by the luxurious combination of chocolate brown with other neutrals, often through accessories like a structured tote or leather jacket.
Practical Tricks for Instant Elevation
The stylists shared numerous quick tricks that instantly polish a look. Miyasaki recommends the French tuck and rolling up sleeves to the midpoint of the forearm. Spencer Sutherland, a musician, suggests putting your shirt collar over the lapels of a suit jacket for a retro vibe. Mignano is into wearing non-white socks that peek out of loafers to add warmth and intentionality.
Other tips include shopping across departments—Upshaw loves the versatility of men's trousers tailored for women—and mixing metals in jewelry with confidence, as Barber admires. Owin Pierson, a travel creator, recommends figuring out your ideal color palette through analysis, while Xandria even matches her scent to her outfit's fabric and color scheme.
Perhaps the most profound transformation comes from embracing change that reflects one's life. Tony-nominated actress Brenda Braxton shaved her head at 60, calling it a declaration of freedom and self-love that became part of her powerful, regal signature look.
The Ultimate Chic Secret: Unshakeable Confidence
Ultimately, every expert tip circles back to a central theme: authentic confidence. As Rachel Lovely perfectly summarizes, "The chicest thing anyone can do... is wear something they love and feel comfortable in." She asserts that when someone feels authentically themselves, it radiates and will always be chic.
From timeless investments and perfect tailoring to bold personal statements and clever styling tricks, chic is less about a single prescribed look and more about a mindful, confident approach to dressing. It's the art of looking effortlessly like yourself.
