Q: I am in my second year of college and I always dress up to go to class. How can I look nice but avoid looking like I'm trying too hard or overdoing it?
A: You had me in your palm when you wrote, "I always dress up to go to class." Hooray! Not looking like we tried too hard is a true fashion challenge—at what point do we cross the line? For me, I ask myself whether this look has become a costume, because if it's not Halloween, then a costume isn't what we should desire. Take the pattern-mixing that I love to do with my suits, shirts, ties, and pocket squares—there's a lot going on. I champion the style and I feel confident in it. But if I were to pair it with a monocle and a riding crop, then I'd be in a costume. It's all about editing and the right balance. A denim jacket is the perfect way to tone down a silk dress. And stick to flats instead of heels—a pair of loafers or mules are preferable to sneakers. If you believe that your look is trying too hard, then it probably is. Continue to be a fashion leader!
Q: I am obsessed with extremely bright accessories, but how does one incorporate those eye-catching pieces into a simple, classic wardrobe?
A: Frankly, "a simple, classic wardrobe" is the best possible partner when wearing bright accessories. In my experience, vibrant handbags, shoes, and jewelry should be thought of as statement pieces, and they can only be a statement—or to use your term, eye-catching—if they're the star of your head-to-toe look. If your entire outfit is bold and colorful, then you'll risk looking like a cartoon character. Furthermore, be aware of the color relationship between your accessories and apparel. For instance, neon goes best with black or white; jewel tones are enhanced by neutrals and pastels.
ONE OF THE GUYS
Q: I am starting a new position at a baseball stadium where my coworkers dress business casual. I typically like to add some creative flair to my outfits, but I can't show up in a dress and heels at the office without raising eyebrows. What should I wear?
A: Only knowing that you work at a baseball stadium, I want to suggest that you consider pants as an opportunity to experiment. For tops, choose those with intricate constructed details such as pleating, peplums, and godets that provide a counterpoint to the pants. Consider tops with embellishments like beading, and, of course, color, color, color. Finally—and because I don't know your size and shape—be very mindful about scale, and remember my mantra: silhouette, proportion, fit. You don't want your clothes to overwhelm you.
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