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Through our partnership with Singlewood, four individuals received a personal styling experience with the espy team. Each winner worked with a stylist to refresh their wardrobe and explore clothing that better reflects their lifestyle today.
Next up in the Styled by espy series is Ryan.
Ryan works as an administrator and manager in a medical office, where his days balance professional responsibilities with a relaxed business casual environment.
Outside of work, his life is a mix of music, movies, travel, and spending time with friends. Weekends often include exploring Inglewood, trying new restaurants, or catching up with people close to him.
Recently single after a long relationship, Ryan saw this makeover as an opportunity to focus on himself and start feeling more confident in his appearance as he steps into a new chapter.
Like many men, his wardrobe had gradually settled into a routine of hoodies, T-shirts, and jeans in neutral colours. While comfortable, he felt there was room to elevate his everyday style without sacrificing the relaxed feel he prefers.
Another challenge Ryan faces is fit. Being shorter means finding pants that fit properly can be frustrating, and tailoring often feels like an extra barrier to updating his wardrobe.
Working with an espy stylist allowed Ryan to explore new combinations, silhouettes, and layering options that feel natural while still looking more polished.
“Most of my wardrobe has been hoodies, T-shirts, and jeans. I wanted to keep that comfort but make things feel a bit more put together, especially for work and going out with friends.”
Ryan was looking to build outfits that feel natural to wear while still looking more elevated.
His goals included:
• Comfortable pieces that still feel sharp and intentional
• Business casual outfits that work in the office
• Looks that transition easily into evenings and weekends
• Layering options like button-ups, polos, and sweaters
• Better-fitting pants that complement his build
Our stylists focused on modern fits, smart layering, and versatile pieces that help Ryan feel more confident without overcomplicating his wardrobe.
Ryan’s first look builds on his comfort zone while introducing more structure and personality.
Layering a textured knit under a bold patchwork jacket adds visual interest while keeping the outfit relaxed. A clean white tee and modern denim ground the look, while leather boots bring a more polished finish.
It’s an easy everyday outfit that feels comfortable but noticeably more styled than a typical hoodie-and-jeans combination.
For Ryan’s work environment, business casual means finding pieces that feel professional without being overly formal.
A lightweight quarter-zip sweater layered over a patterned button-up creates a polished yet relaxed look. Paired with modern jeans and classic brogue shoes, the outfit works perfectly for the office while transitioning easily into dinner plans afterward.
Ryan came to espy looking for clothing that would help him feel more confident while still staying true to his personal style.
If your wardrobe feels stuck in a rut or you’re unsure how to elevate your everyday outfits, our stylists can help you build a wardrobe that suits your lifestyle.
Book a Personal Styling Session Today
Introducing a blazer into Ryan’s wardrobe adds an entirely new level of versatility.
A modern check blazer layered over a merino crewneck creates a refined but approachable look. Paired with clean performance denim and sleek sneakers, the outfit feels polished without feeling overly formal.
It’s the kind of look that works equally well for dinner, events, or social occasions.
Layering is one of Ryan’s favourite styling approaches, and this look builds on that preference.
A patterned polo under a quarter-zip sweater creates texture and depth, while a lightweight bomber jacket adds structure to the overall outfit. Tailored denim and classic brogue shoes complete the look with a balance of comfort and sophistication.
It’s a versatile outfit that works across multiple settings, from workdays to weekends.
When Ryan arrived, the focus was helping him elevate the pieces he already enjoys wearing while introducing more refined layers and better-fitting silhouettes.
By updating his denim fits, incorporating textured outerwear, and adding versatile layers like sweaters and blazers, we created outfits that feel natural for Ryan while helping him look more polished and confident.
Ryan’s styling experience wasn’t about replacing his personal style. It was about refining it.
By building outfits that balance comfort and structure, Ryan now has pieces that work across different parts of his life — from the office to evenings out with friends.
Sometimes, a few thoughtful updates are all it takes to transform the way your wardrobe works for you.
If your wardrobe feels outdated, repetitive, or simply no longer reflects who you are today, our stylists would love to help.
Book a Personal Styling Session Today
Ryan is the second feature in our Styled by espy transformation series. Stay tuned as we continue sharing real client styling stories and the impact of a personalized styling experience.
