Nine Ways Pitti Uomo Street Style Can Improve Your Own Personal Style

by Barron Cuadro  |  in Style Tips

Twice a year, menswear industry heavyweights (retailers, buyers, designers, magazine editors) flock to Florence, Italy to view upcoming collections at a tradeshow called Pitti Uomo.

Even if you’re a menswear “beginner”, just starting to hone in on your style, there’s a good chance you’ve come across a photo of men at this event in your search for style inspiration.

If you take one glance at these photos, you’ll quickly see this is personal style to the 9000th degree, and you can’t deny the uniqueness and vibrancy of each attendee’s outfit.

florence italy
Via Flickr

How To Get The Most Out Of Pitti Uomo Street Style Photos

Even if you can’t imagine wearing such bold ensembles, doesn’t mean you can’t pick up a thing or two from the guys at who roam the streets of Florence at this event.

If you’re still in the process of figuring out your own personal style, here are some ways you can let Pitti inspire you, and lessons you can learn.

1. Focus on one element of a particular style

9 ways Pitti Uomo Can Improve Your Personal Style
Photos via The Sartorialist

When you browse through photos of Pitti, you’ll notice it’s a dizzying array of colors, patterns, textures, and fit. Everything is all over the place.

If you want to truly benefit from all this style inspiration, I encourage you to focus on one particular element about an outfit you like.

Maybe it’s how a suit fits, or a specific color combination, or the way accessories finish off an outfit.

Don’t try to be that guy exactly, but if you realize he put together a great color combo you never considered before, take note, and experiment with it the next time you’re wearing a suit.

2. Be Just a little Bit daring

There are more exciting things than bold socks. Don’t constrain yourself to only experimenting below the knee, and under your pant leg.

  • For starters, if you wear a lot of solid shirts, try incorporating a bold stripe in a vibrant color.
  • If you usually stick to solid white pocket squares, go pick up something more exciting. Find a tie with an interesting paisley or floral motif.
  • If you only own solid suits, and assuming you have your Lean Wardrobe basics down, invest in a few with more exciting fabrics and patterns.

You have plenty of options! And if you’re afraid of going overboard, if you start with just one bold color or pattern, you’ll be fine.

3. Try On different fits And Silhouettes

9 ways Pitti Uomo Can Improve Your Personal Style

Maybe all slim and shrunken isn’t your style. Perhaps you prefer a more traditional length jacket, or trousers with a fuller leg.

Like I always say, style is personal and subjective, and just because one thing is currently “in style”, doesn’t mean that everything else is suddenly passé.

I love menswear writer Ethan Wong’s take on being less stuffy and more slouchy with his clothing and style.

I also love where my friend Tim Dessaint is taking his personal style. Wider silhouettes, shopping in the women’s section, etc.

If you find yourself saying, “Style X is wrong because I read that rule XYZ says so,” take a breath and realize most style “rules” are just guidelines from one person’s perspective. The truly stylish man knows that once he masters the basics, he can break the rules however he wants, because he’s doing so intentionally.

4. Find your Style tribe

This is important not just in style, but also when it comes to general life interests, work, and business: you need to surround yourself with like-minded people who can push you to be better. That’s how you grow and evolve!

So in matters of style, if you care about your appearance and understand the importance of dressing well, it’s important to find people who also feel the same way.

If you’re lucky, you’ll find them in your hometown or where you work, but even if you don’t have anyone locally, you have this amazing resource called “the Internet”, where you can connect with people across the world who share similar interests. Pretty crazy, right?

5. Accessories Are The Extra 10%. Use Them To Your Advantage

In terms of personalizing an otherwise bland ensemble like a grey or navy suit, it’s all about what you pair it with. A navy suit can be interesting if you use it as a canvas for interesting color and pattern combinations, starting off with a killer tie and shirt combo.

Where do you go from there?

Maybe try a wool fedora (or a Panama, if it’s summer). Find a great pair of sunglasses. Experiment with lapel pins, bracelets, colored laces, and large print pocket squares. But please, don’t wear all your accessories at once. Otherwise it looks too over-the-top, too much going on.

Experiment with one, maybe two (max), and see how creative you can be without going too over-the-top.

6. Invest in quality Goods

In case it wasn’t obvious, these guys wear expensive suits. But you don’t have to spend tons of money on the most expensive clothing right away, especially when you’re still figuring out what you like, what silhouettes look best on you, and what your general style is.

Start small and build your Lean Wardrobe piece by piece. There’s no need to rush.

When you’ve finally developed your preferences, your sense of taste, and you know what you like and don’t like… then you can start to invest in nicer things.

Not sure what to start with? I usually suggest upgrading your winter coat, your leather dress shoes, or your watch. These are things you don’t have to buy as often. Suits are another worthy investment; if you buy something relatively timeless, you can wear it for years.

Raphael - Gentleman's Gazette - 9 ways Pitti Uomo Can Improve Your Personal Style

In this photo above, my buddy Raphael from Gentleman’s Gazette is wearing a Ralph Lauren Purple Label suit he found on eBay twelve years ago.

Not only did he get it for a bargain—RLPL suits start at around $4,000—he also bought it TWELVE years ago (twelve!) and can still wear it today. Sadly, I can’t say the same about my JNCO jeans.

Speaking of timeless…

7. “Simple and timeless” never Goes Out Of Style

While it’s fun to see the creativity in all these outfits, I think you can learn a lot from the more traditional styles you find.

As you browse through the photos, you’ll see them little by little, and one thing that you start to realize is that simple and timeless actually stand out.

Regardless of whether you’re among menswear peacocks or office drones, you can stand out with a classic style, as long as you have the perfect fit and display a bit of confidence.

My buddy Al Bizzy does the classic tailored (yet comfortable and casual) look really well.

8. Find creative and affordable ways to add variety

Dressing well doesn’t have to be expensive either. If you have a bit of patience and a good eye, you can explore vintage and thrift shops in your area.

Ethan, who I mentioned earlier, is a big fan of shopping vintage and he’s found some great stuff over the years. If you’re local to or ever visiting NYC, Sean Crowley has an incredible vintage shop, Crowley Vintage, in DUMBO, Brooklyn… and that’s just one vintage shop of many in this city.

If there aren’t any good thrift shops near you, you may want to explore your online options.

Obviously, eBay is a great place to start. Crowley Vintage ships worldwide, I believe. Carraway Concept has some great new and vintage pieces on their site. I love Broadway & Sons, a Sweden-based military vintage shop. They ship worldwide. And the guys at Put This On covered this idea of online thrift shopping in detail.

Here’s a tip:

  • Build your Lean Wardrobe first, which will handle your basics and essentials.
  • From there, experiment with more exciting colors, patterns, and texture combos in your shirts and accessories
  • When you’ve found your groove and more deeply understand your own personal style, step it up to unique coats, shoes, and suits.

If you start this way, you can dabble affordably (a $50 shirt vs a $500 suit) and not break the bank, and while experimenting, you’ll better understand how to mix patterns and pair colors, and in general, will get a good sense of what works and what doesn’t.

9. Confidence is king

You can have the best fitting, most pimped out suit ever, but if you’re uncomfortable wearing it, that lack of confidence will show.

Learn to be comfortable with your style. And if you’re not comfortable yet, wear things you don’t normally wear more often so you get used to it.

Here’s an example. In the mid-2000s, bootcut denim was having a moment. I, myself, had a few pairs. When that look grew tired—wasn’t it inevitable?—I started to transition to straight leg denim.

At first, I thought straight legs looked really weird (e.g. “Why isn’t the leg opening covering half my shoe anymore?”) and I was resistant to change, but I kept wearing them anyway.

After a week, I was already accustomed to it. After two weeks, straight leg denim felt natural, and I was much more comfortable and confident wearing them.

All you gotta do is stick it out and let yourself get used to the new look or style.

Another thing: dress well, even—or especially—when it’s unexpected, so you get comfortable with other people’s inevitable reactions. Things like:

  • “Why are you so dressed up?”
  • “You got a job interview or something?”
  • “Where you headed, why so fancy?”

Most of the time, these come from people closest to you, like your friends, family, and coworkers.

They don’t mean anything by it (most of the time), they’re just not accustomed to your new style. So the best thing you can do is wear more of it, more often, so they get used to it.

Got it? Good.

I’ve talked to a lot of guys who are just starting out, and oftentimes, finding their confidence is the toughest part.

Owning your look and not worrying about being the best dressed person in the room just takes some balls, and a bit of practice.

Learn to be comfortable and confident in what you wear, and that confidence will reflect not just in your ensemble, but also in your body language.

What have YOU learned?

I picked up these nine lessons by observing the guys who attend Pitti. What lessons have you learned?

Thanks to The Sartorialist for taking these photos. Beautifully captured, as always. Top photo via flickr.