(The above photo was taken by Tricia Anne Photography)

I can’t believe I was able to go to Italy. It always seemed like something I would do much later in life. But sometimes opportunities present themselves!

This vacation  was done because my mom wanted to celebrate her wedding to my stepdad. They had actually got married (on paper) last year in a simple ceremony in their local courthouse but being my mom, she eventually realized that she wanted something big, or at least bigger than that. (I realize how much of this sounds like a sitcom plot). Ever since I was a kid, she, had always wanted to have a ceremony on Lake Como just like Anakin and Padme. At the time, I assumed that it was going to be a renew your vows sort of thing, but once she and my dad split up over a decade ago, I had a feeling that she was going to bring it back. Sure enough she did, and we eventually started planning for this trip to Italy. 

This was a going to be a big trip. We had to balance a wedding with typical Wong Family tropes like plenty of museums and walking tours. This was also going to be our first international trip as a family since our Japan trip back in 2019. Thankfully my mom is a huge planner, so we had an itinerary done well in advance (with plenty of time for solo excursions and  menswear stuff). The group was also larger. Since this was a wedding trip, we would be joined by my mom’s sister and husband, my stepdad’s friends as well as his kids and their partners; my brother and I would be joined by our partners as well. 

It was quite expensive, but we all saved up for a while because we knew we all wanted to have a fun time. This trip was not only a celebration of love (I’m very happy for mom and Richard, they are a great match!), but for life as well. We’re very lucky that we were able to do this, especially as my brother and I get older and become more independent with our adult duties. I’m also thankful that my new career allowed for this time off!

Let me be frank with you all:  I was actually more nervous than excited for this trip. Outside of these family vacations, I don’t really travel. As some of you guys know, I mainly spend my free time doing local things solo or doing relatively low key hangouts with my friends. I don’t even go to NYC as often as you’d think!  International travel means large crowds, long flights, and a packed itinerary. There’s a lot of rushing, a lot of anxiety, and plenty of things that can (and did) go wrong; my nerves can only take so much. But obviously this was worth it. 

We were set to be gone for around two full weeks, which I think is the longest trip we have ever undertaken. There was also the fact that we had multiple destinations to hit while in Italy, which meant that we were going to be bouncing around every 2-3 days. I haven’t done that since my high school senior trip, where we went to a few cities on the East Coast (DC, Philly, etc) in a week. Packing two weeks worth of clothes into a carry on (we don’t check luggage) was going to be a challenge. Add the fact that I’d need to pack comfortable travel clothes for planes and buses in addition to wedding attire and menswear stuff for dinners and Going Out, and you’ve got fodder for me to become a capsule wardrobe proponent.

But as you’ll see in the recaps below, I was able to do it! I normally hate packing for trips because I always feel like I have to wear athletic clothes or something that doesn’t feel like me; in other words, I was scared of looking like a “stranger” or not like myself when I’m out. The alternative would be that I’d have to suffer for my clothes, which I also don’t like to do; I don’t want to be that menswear guy. However, my wardrobe has gotten much better over the years, in quality, design, and intentionality. I could wear practical pants, button ups, and tailoring while being appropriate and being me. My goal is to always look like myself and you guys know that I’ve been working to achieve that even if I am not dressed like Esquire Man everyday.

 All of this to say that what I brought to Italy has to be the best travel wardrobe I had ever done. It’s full of tee shirts and button ups (a mix of spearpoints and sportshirts), as well as one pair of shorts, two chinos, one odd trouser, three shoes, as well as a tux and a single suit. I know it still sounds like a lot, but not only was I able to pack it all, but I actually had a chance to wear all of it. Hell, I even rewore items (thank you handwashing).  I actually wore the tees the most during the beginning of the trip due to a lot of moving around. It was until we got to Milan, Florence, and Rome that I ended up wearing full tailoring, even if it was for just the evening. Hell, it wasn’t even that often; because of all the museum days, I seldom had a chance to go back to the hotel to change and then go out again. I was still glad I was able to do it for some evenings though, as it added to the sense of occasion.

Obviously this intro has gone long enough, which is why I actually split the trip up into multiple recaps which you can read about below. Each one will have a rundown of the outfit I wore each day while including the context for the days’ activities. Keep in mind that most of the content is centered around family, date nights, and museums/walking tours. This also contains the most general photography than any other blog post before it!

This is indeed a menswear blog, but it should be clear by now that I want this to be about my friends and I wearing menswear in our daily lives instead of being a shopping guide.That certainly holds true with this series. I think that plenty of other menswear blogs have covered that and I even used them to figure out what I wanted to check out. Simon’s Florence guide comes to mind. I also simply went to places that were recommended to me by people on Instagram.

As a result, the individual articles do have some menswear shop visits, but don’t expect to see photos from Liverano’s backroom or an interview with Kenji Kaga. I was in Italy for family and I happened to have time to do my menswear thing in between them. On another crazy note, this was also the first trip where I did not meet up with any menswear people…until we ran into Sora at the very end! Again, this was about family and I was very happy I got to hang out with them in a beautiful country.

However, I do have a few general menswear notes I’d like to share with you guys:

• Italians do indeed dress well, especially the well-to-do corporate guys in Milan, Florence, and Rome. It does seem like Pitti 2017 in the best way possible: sensible navy and grey suits in broad, soft shoulders (most with spalla camicia), bengal shirts, geometric ties, and riding bicycles.  The peacocks are usually the ones working in menswear stores or are the rich ones at the bars or on dates.
• As you could expect, the best dressed people are the elderly guys who just seem to kill it, whether it’s in tailoring or classic sportswear (utility jackets, scarves, straw hats). Unfortunately, I didn’t take that many street style photos.
• Tourists abound, mainly from other places in Europe. They either dress like peacocks or in athletic+casual clothes (polos and stretch pants, sandals). 
• Young people, both Italian and tourists, dress very tiktok-y. Think of the “old money” aesthetic that’s currently trending: big blousy shirts, short shorts (or wider legged pants), and Doc Martens or white sneakers. 
• Like Japan, there are a lot of menswear stores that seem to be their version of Men’s Wearhouse. However, a lot of it is pretty good in the sense that the styling is closer to #menswear than 90s dad core. Neapolitan-ish details abound! The prices seem to indicate that they are closer to fast fashion, but the selection looks  much better than what we’d see in an American mall. 
• Vintage is incredibly pricey here. I’m talking over 150 Euros for a jacket or suit!  I’m not sure what the culture is around vintage, but most places seem to be curated and there aren’t a lot of thrift stores. I couldn’t seem to find much tailoring and if I did it wasn’t bespoke. Instead it’s either designer (Gucci, etc)  or 60s/70s vintage. And then of course there is a lot of vintage Americana like field jackets, WWII chinos, Levis, and cowboy boots. I wanted Italian things, so I wasn’t too impressed since I could find much of that back home.
• There are a lot of leather stores in Florence, all selling handbags, belts, and jackets in various colors. They suspiciously all have similar designs and even all have similar basic names like “David’s Leathers” or “Leonardo Leather Jackets”. I wonder if they all have the same supplier!
• I didn’t really buy much!

And now for some general notes from the trip:

• Churches are beautiful! They made up a majority of the things I visited since each one has amazing pieces of art.
• Food and drinks are cheap here, at least I think that’s the case as I didn’t always convert to USD in my head. Either way, we all ate a lot and drank quite a bit of wine at almost every meal.
• It’s actually great to eat outside. This is probably the Angelino in m , but I never fully enjoyed al fresco dining until going to Italy. Perhaps that’s because Italy just has a great culture around eating and hanging out, making for an entire vibe that feels inviting, even if your table is so small and it’s humid outside. It just feels right to eat out in a cobblestone street, surrounded by dozens of other people in other trattorias. I’m sure NYC is similar in that regard.
• Everyone was so friendly! I was actually nervous about not knowing much Italian.
• Walking 20K steps everyday can be bad in leather shoes, but it wasn’t as bad as I thought. This may be due to better shoes (Alden and not thrifted, well-worn AE’s as I did in years prior) but I did get blisters about a week in. Maybe I’ll need to buy Salomons or something next time…
• Walking does lead you to some great places (and most places in Italy are fantastic), but there is a big lack of places to rest. Almost every step and fountain is taken by other people and you can’t really sit at a table/chair outside unless you’re ready to eat or drink at that establishment. Maybe Italians are used to being on their feet all day and only delicate Angelinos need a bench every five minutes!
• I had a tote bag with me at all times with an umbrella, portable battery, cameras, and snacks (and water bottles). This was incredibly handy as I used all of them multiple times throughout the trip. However, it meant for a sore shoulder after long days of tours.
• If Japan has vending machines every 10 feet, then Italy has gelaterias. And boy are they all good. Almost every place had a line, whether it was a one off shop or a chain.
• Bistecca is as great as you think it is. No wonder all the guys at Pitti eat it. It’s also cheaper than an American steak! 
• Hotel Breakfasts are great and I made sure to drink plenty of coffee and eat a lot of fruit everyday for energy. We were incredibly lucky to have good hotels for each leg of the journey.
• We didn’t take a lot of trains or buses— we just walked everywhere! Unless it was a big destination of course, like the Vatican or a trip to Pisa.
• The sun set around 8:30PM everyday. We had plenty of light, at all times which was crazy!
• It’s also fun to talk to other travelers!

Overall, this trip was truly something special. I got to do so many things, from seeing all the cultural sites (like the Path of Illumination) to the #menswear pilgrimages, not to mention being able to see my mom’s wedding! 

The best part is that I go to do it with Isabel. She wasn’t just a trooper. She was excited and enthused to be there with me for all of it, suggesting churches, stores, and restaurants all along the way. She was a true partner in all of this, which made for a much better trip than if it was just me. I was actually concerned about traveling with both my your family and my significant other, but I was able to make the best of it and split our time accordingly so that no one felt shortchanged. 

This has to be one of the best trips I’ve ever taken. It also allowed me to take some of the best photos of all time as well, though much of that can be attributed to the architecture and lighting that is already inherent to those places. I’m just snapping the shutter.

Alright, I think you guys are ready to dive in! Check out the different blog posts below. I also did a podcast episode on it, which you can listen to in browser here or use any podcasting platform you wish. Enjoy! 

Podcast Outline

• 10:51 – Ethan Went to Italy!
• 13:21 – Packing for Italy
• 19:38 – Food Recap
• 27:04 – What Clothes Did Ethan See?
• 34:40 – Tourist Talk
• 44:26 – Ethan and Menswear in Italy
• 1:11:52 – Wrap-up

Blog Posts

• Lake Como
• The Wedding
• Venice
  • One visit to Humana Vintage (a bit like a Crossroads or Buffalo Exchange)
• Florence
  • Liverano & Liverano
  • Tie Your Tie
  • DesiiVintage
  • Clochard Vintage
  • Humana Vintage
• Rome
  • Wools Boutique
  • More Humana Vintage
  • Handful of random stores

My Tiktok Vlogs

Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord. Oh and don’t forget, we do a podcast every two weeks!

Buh-bye!

EthanMWong | StyleandDirection

The Podcast is produced by MJ.

Big thank you to our top tier Patrons (the SaDCast Fanatics): Austin, Philip, Shane, Henrik, and Alexander.