Finally made it to Florence…
After an epic journey from DC to Rome, then by train to Florence, I’ve arrived at the stunning Bottega Veneta Suite at the St. Regis Florence. With the Arno River flowing right outside my window, this will be my base camp for the 108th edition of Pitti Uomo—and what a week it promises to be.
Understanding Pitti Uomo: More Than Just Menswear Theater
If you’re a casual menswear enthusiast who’s never experienced Pitti firsthand, the endless stream of photos might make it seem like nothing more than well-dressed men posing with cigars and Negronis—what I like to call the “influencer petting zoo” (trademark pending).
While there’s certainly some of that spectacle, Pitti Uomo is fundamentally the world’s most important menswear trade show. Held twice yearly at Florence’s historic Fortezza da Basso, it’s where global brands showcase collections to buyers and press, where industry trends are born, and where the business of menswear gets done.
Think of Pitti like a perfectly balanced Negroni—equal parts trade show, social events, and networking opportunities. Each component is essential to the whole experience.
My Four-Point Pitti Strategy
I don’t come to Florence just to stand around looking stylish (though that’s certainly part of it). My approach centers on four key objectives:
1. Networking: The menswear world is surprisingly intimate. Every conversation could lead nowhere—or everywhere. Building genuine connections remains crucial in this relationship-driven industry.
2. Brand Awareness: Beyond my online presence, the He Spoke Style Shop offers direct access to my entire tailored wardrobe through what I believe is the best value in online custom menswear.
3. Event Hosting: For three consecutive Pitti editions, He Spoke Style has partnered with Michael Andrews Bespoke and Angel Ramos New York to host memorable events, including our Monday night creative black tie aperitivo at the St. Regis Winter Garden—now known as Pitti’s unofficial opening ceremony.
4. Content Creation: Documenting the experience for our community while collaborating with partners creates lasting value beyond the week itself.
The Art of Pitti Dressing: Seven Themed Looks
Rather than pack randomly, our six-person team established daily themes to create visual cohesion while allowing individual expression. Here’s how I interpreted each concept:
Black Tie Creative
Sometimes the best creativity lies in restraint. You could argue that my interpretation isn’t overly creative, and you wouldn’t necessarily be wrong, but this represents exactly how creative I’m personally comfortable being within formal dress codes. My go-to strategy always revolves around selecting a standout dinner jacket that does the heavy lifting.
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This light blue option features incredible texture and breathable fabric perfect for Florence’s summer heat. The color makes a statement without veering into costume territory. I’ve paired it with a pleated front tuxedo shirt—my signature move for elevating formal looks beyond the standard.
White suspenders provide both function and classic appeal, while a coordinated stud set paired with vintage cufflinks adds personal history to the look. A midnight bow tie bridges the color palette beautifully, and patent leather loafers ground the ensemble with traditional formal footwear.
Tonal Tuesday
Earlier this year, I coined “Tonal Tuesday” and it resonated so well that it’s now become a recurring theme. While you might recognize elements from a previous video, I made key updates to keep it fresh and perfectly suited for Pitti. The foundation is an ivory twill suit that’s honestly become one of my favorite pieces of the season.
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I’ve paired it with a sand-colored chambray shirt that creates subtle contrast through texture rather than color. This is where tonal dressing really shines—when you remove the distraction of contrasting colors, you focus on the interplay of textures and subtle shade variations. The chambray’s casual weave against the suit’s smooth twill creates visual interest without breaking the monochromatic harmony.
Brown suede accessories maintain this tonal approach while complementing the warm undertones, and vintage-inspired sunglasses add old-school sophistication. The overall effect is polished yet relaxed, perfectly capturing that effortless Italian elegance that Pitti embodies.
Technicolor
To be honest, I initially considered sitting out technicolor altogether. Lots of bold color isn’t my natural wheelhouse, but I found an approach that allowed me to participate authentically while staying true to my aesthetic. The key was discovering the perfect vehicle: a new merlot bamboo sport coat.
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Bamboo fabric—sometimes called California cashmere—is magical for summer dressing. It offers cashmere softness while being significantly more breathable and practical for warm weather. The rich color provides the pop the theme demanded without feeling garish. I’ve supported the colorful jacket with a light pink shirt and ivory trousers that create a sophisticated tonal story.
The magic of bamboo extends beyond comfort—people literally cannot stop themselves from touching it, which creates wonderful conversation starters at an event like Pitti where networking is crucial.
Pitti PI
The “Pitti PI” theme presented classic Magnum archetypes: aloha shirt with nut-hugger jeans, or casual top with scandalously short shorts. This is Pitti, not Halloween, so I took that Tom Selleck inspiration and filtered it through my personal style lens. The centerpiece became a silk-cotton camp collar shirt that perfectly captures that relaxed Hawaiian vibe while maintaining sophistication.
The key styling decision was tucking it in—direct homage to Magnum’s always-tucked approach, but executed with tailored trousers rather than those infamous tight jeans. A ribbed t-shirt underneath adds comfort and authenticity to the tropical aesthetic, while white cotton trousers provide a clean foundation that’s decidedly not of the nut-hugger variety.
The baseball cap brings that essential sporty American element, while vintage-inspired sunglasses maintain the retro feel without becoming costume-like. What makes this work is finding balance between paying homage to an iconic character and creating something genuinely wearable for the setting.
Classic Black Tie
Wearing a tuxedo in summer isn’t a problem if you have the right tuxedo. This wool-mohair blend “truly tropical tuxedo” maintains all the elegance expected from black tie while being genuinely comfortable in warm weather. What I find fascinating about black tie is how deceptively simple it appears, yet countless small details must come together perfectly.
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I’ve chosen a self-textured tuxedo shirt to keep things ultra-classic while adding just enough visual interest to elevate beyond basic rental-wear territory. The coordinated stud set and cufflinks create consistency across metallic elements, while the silk cummerbund provides that essential finishing touch separating proper black tie from merely wearing a black suit.
The beauty of traditional black tie lies in its democracy—when executed properly, the clothes become a backdrop that allows personality and conversation to take center stage. There’s something liberating about knowing you’re dressed appropriately for virtually any formal occasion.
Bringing Preppy Back
Preppy style never truly goes away—it just takes periodic breaks before returning with renewed relevance. For this theme, I wanted to showcase a new sport coat that replaces a beloved piece that proved so popular it sold out completely. This alabaster glen plaid sport coat represents everything I love about preppy tailoring, with subtle plaid that provides visual interest without being overwhelming.
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The supporting garments read like a greatest hits of preppy essentials. The light blue Oxford cloth button-down is perhaps the most democratic piece of menswear ever created, while khaki cotton trousers create that effortless American ease that preppy style does better than any other aesthetic. The proportions are spot-on—structured enough to look polished but relaxed enough for long trade show days.
What elevates this beyond basic country club uniform is attention to details and proportions. The sport coat’s cut is contemporary while respecting traditional lines, and classic penny loafers with textured socks add visual interest at the foundation.
Black & White
A black suit in summer might seem questionable, but like the tropical tuxedo, this proves that fabric selection makes all the difference. Constructed in tropical wool, this suit maintains the visual impact of black suiting while remaining genuinely comfortable in Florence’s warmest weather. The real personality comes from the silk-cotton shirt with its fun pattern that’s perfect for summertime dressing.
The styling gets interesting with the collar worn outside the suit lapel, creating classic 1970s swagger that feels both nostalgic and contemporary. This detail requires attention to ensure the collar sits properly over the lapel both front and back, but when done correctly, it transforms the outfit’s entire attitude from corporate to creative.
Classic sunglasses add sophistication while ostrich leather shoes provide unexpected texture that elevates the look beyond standard business attire. The overall effect is polished but with personality—exactly right for Pitti’s unique blend of business and style theater.
The Complete Pitti Experience
These seven looks represent more than just outfit choices—they tell the story of how thoughtful dressing enhances every aspect of the Pitti experience. From networking opportunities created by conversation-starting fabrics to the confidence that comes from wearing perfectly fitted formal wear, each ensemble serves both practical and aesthetic purposes.
The beauty of Pitti lies in its unique combination of serious business and sartorial theater. Whether you’re navigating trade show floors, hosting evening events, or simply appreciating the incredible creativity on display, having a well-planned wardrobe allows you to fully engage with everything this remarkable week offers.
Most importantly, these outfits prove that developing your personal style doesn’t mean abandoning your comfort zone—it means understanding it well enough to stretch its boundaries thoughtfully. The best dressed men at Pitti aren’t wearing costumes; they’re wearing elevated versions of themselves.
Thanks, as always, for reading.
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