Day 1 of Pitti Uomo 108: 17 Handpicked Snaps of the Coolest Men’s Looks

On June 17, 2025, Pitti Uomo 108 kicked off, bringing together stylish men from around the world, as it does every year.From the latest snaps just taken by the OTOKOMAE editorial team, we’ve carefully selected photos of celebrities and men with particularly stylish outfits to share with you!

Pitti Uomo 108 DAY 1: Carefully Selected Snaps 1To Wear Barrel-Leg Pants in a Modern Way, Pair Them with a Polished Look

We spotted Daniele Biagioli, a Pitti Uomo regular who has appeared in OTOKOMAE articles numerous times.During the height of the streetwear boom, he stood out for incorporating streetwear brands’ outerwear and hyped sneakers into his looks, but since around last year, he’s been creating a modern vibe centered on the dressy style he’s always excelled at. On the first day, he showcased an outfit reminiscent of the Ivy League style.His barrel-leg chinos add a contemporary touch—a great example of how a mature man can pull off this style.

Pitti Uomo 108 DAY 1: 2 Carefully Selected SnapsIf You Want to Stay Ahead of Trends, Are Slim-Fit Pants a Good Option!?

Next up is Domenico Gianfrate’s outfit.At a time when loose-fitting pants are at their peak, he made an appearance wearing skinny pants. When the OTOKOMAE editorial team asked him about his reasoning and the future of trends,he said, “Slim-fit pants will likely become more prevalent going forward. With loose-fitting pants currently at their peak, I chose to wear skinny pants on purpose to stay ahead of the trend.”

Pitti Uomo 108 DAY 1: 3 Carefully Selected SnapsLoose Silhouettes Are the Current Mood for Suits and Jacket-and-Pants Styles

For suits and jacket-and-pants styles, keep an eye out for silhouettes that are just a touch looser than usual.The suit worn by this gentleman consists of a double-breasted jacket with a longer body length and a low gorge line, paired with slacks that fall to about mid-calf. For such a style, I’d recommend pairing it with classic loafers, as he has done. Alternatively, slip-on shoes like Loro Piana’s “Summer Walk” are also a great option.

Additionally, while not worn by attendees, the collection showcased by Brunello Cucinelli at their exhibition booth was emblematic of this suit style. The suit displayed on the left in the image combines a structured jacket with shoulder padding and loose-fitting slacks, fully reflecting the current trend.

Pitti Uomo 108 DAY 1: 4 Carefully Selected SnapsPitti Uomo’s Fashionistas Are Obsessed with Loafers!

I’d also like to mention how loafers stood out on the first day of Pitti Uomo.Men were seen here and there pairing loafers not only with dressy outfits but also with streetwear-inspired looks. For example, this man paired loafers with a streetwear-inspired outfit featuring a cap, a decadently designed camo jacket, distressed jeans, and Adidas socks.

Editorial Department, Irie

Personally, I had expected to see more people wearing low-profile sneakers—partly as a reaction to the trend of bulky sneakers that was all the rage a few years ago, and partly because luxury brands have been releasing them in succession. However, what I actually saw most often on the first day at the venue were men wearing loafers. Perhaps this is because Pitti Uomo is primarily focused on formal wear.I wonder if loafers will also be the footwear of choice for attendees at the upcoming Milan and Paris Fashion Weeks. I’ll continue to keep a close eye on what the fashion-forward are wearing on their feet.

Pitti Uomo 108 DAY 1: 5 Curated SnapsTo Stay a Half-Step Ahead, Focus on How You Style Your Shirts

If you want to stay a half-step ahead with your spring/summer style, make a conscious effort to incorporate shirts.The style-conscious men who frequently appear in OTOKOMAE articles stood out for actively incorporating shirts, shifting away from T-shirts. Wearing just a shirt on its own or pairing it with a T-shirt underneath—both are valid options. This season, why not try a refined, casual outfit centered around a shirt?

Be sure to check out the gallery below for these and other styles.

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