THE LOOK STRATEGy
Hey, I'm Olivia - The Look Strategist.
Men’s personal stylist AND SHOPPER focused on great fit, confidence, and effortless style.
ABOUT ME
I’m Olivia Gillespie, a New York–based men’s personal stylist with a background in fashion, marketing, and fit-focused styling. I specialize in helping men feel confident in what they wear by creating wardrobes that are intentional, wearable, and true to their lifestyle.​
I believe great style starts with fit and function, not trends. My goal is to make getting dressed easier by offering thoughtful guidance, honest feedback, and pieces that feel natural and polished. Whether you’re refining your everyday look or building a wardrobe from the ground up, I work closely with each client to make style feel simple and personal.
What Most Guys Struggle With:
​Wanting to look sharp without the hassle of shopping or overthinking outfits
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Trying to improve personal style without looking like you’re trying too hard.
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Needing expert guidance—without relying on friends or group chats.
Virtual Styling
For clients who want expert guidance from anywhere
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Includes:
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Virtual lifestyle & style audit (video call or detailed questionnaire)
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Fit and proportion analysis using photos or video
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Personalized color palette and fabric recommendations
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Core wardrobe plan tailored to lifestyle and season
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Done-for-you outfit formulas (casual, work, night out)
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Strategic shopping list with clear priorities
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Brand and category recommendations
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Tailoring guidance and fit notes
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Delivery:
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One virtual consultation
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Digital mood board + shopping plan
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Follow-up support for questions (set time frame)
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Best for: Clients who want efficiency, clarity, and flexibility without in-person shopping.
In-Person/Virtual Styling and Shopping
For clients who want a fully hands-on, white-glove experience
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Includes:
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In-person (or virtual) lifestyle & style consultation
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Closet review and edit (what to keep, tailor, or replace)
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Custom color palette and fabric selection
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Outfit building from existing wardrobe
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Guided in-person shopping
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Real-time outfit styling
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Tailoring coordination (if needed)
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Delivery:​
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Accompanied shopping experience
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Coffee meetings to review wardrobe changes
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Personalized wardrobe roadmap
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Post-appointment follow-up
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Best for: Clients who want a complete transformation with minimal effort on their end.