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My 7 Daily Fits From Pitti Uomo 107 and Milan Fashion Week [With Shoppable Links]

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When you’re going to the center of fashion (Italy), and will be among the world’s most stylish people, what do you pack?

I gave up on trying to be photographed. Instead I wear stuff I love in ways that I’d pretty much normally wear it. Here’s a rundown of my daily fits at Pitti 107 and links to similar pieces.

How I’d pack differently in hindsight

  1. I’d have taken the boiled wool Poszetka Ulster coat I considered but decided against. Had I taken that, I’d have been much warmer.
  2. I need different shoes to wear with my tuxedo. I have Yanko suede Belgians, and for Florentine evenings which include lots of walking, they ruin my feet. The two pairs of shoes I rotated between were my Myrqvist suede chukkas + TLB Mallorca Artista suede penny loafers. Both are wearable and comfortable for walking all day. The Yanko’s chafed my small toe, after the black tie dinner Wednseday night, which then made both other pairs of shoes less comfortable, especially the boots. So after that, I wore mostly the loafers, which fit me nearly perfectly.
  3. I packed every outfit intentionally, taking only 3 additional pair of pants for alternative outfit ideas that I ended up not wearing (I took charcoal twill tailored trousers to wear with the Natalino blazer but went with the cream trousers, my green fatigue pants and slate blue heavy twill chinos).

Outfits by Day Below (Find everything I packed listed together at the bottom)

(Links below may be affiliate links that earn commission when you make a purchase—it’s how I am able to keep making this site and do fun coverage of events like Pitti Uomo. Thanks!) 

Travel fit

This is basically my default travel fit nowadays.

Boltey Harris Tweed worker jacket

Fatigue pants (in either army green or khaki) from Proper Cloth [MUSINGS10 gets you 10% off your first order]

Black long-sleeve polo—Spier & Mackay

Compression socks—OS1st

TLB Mallorca Artista loafers—Skolyx | TLBMallorca.com

Monday, Jan. 13 Daytime Touring Fit

Photo by Joshua of Monogram Styling

Monday afternoon we had a walk through Florence with AION tours. Basically just went casual and comfortable because the main goal was staying relatively warm in the high winds.

Gray Herringbone Eidos Chiaia Coat—This post has current links to the most similar coats

Black Watch tartan shirt—Proper Cloth [MUSINGS10 gets you 10% off]

Navy cashmere sweater—Cavour

Selvedge Denim—Imogene + Willie “Henry” Fit (what I’m wearing) but also consider Gustin’s straight fit (err on sizing up with these)

Warby Parker Butler frames

Myrqvist dark brown suede chukkas

Longines Flagship Heritage Gilt Dial

Filson tote (mine is the open top that maybe doesn’t exist anymore. Having a zipper on it would probably be useful, though I like how easy it is to reach into without a zipper)

Monday Night “Creative Black Tie” Fit

Photo by Joshua of Monogram Styling

These are always the worst recommendations. Lots of guys just wear normal black tie. I’m not fully sold on what I wore, but here it is. Black watch shirt + a scarf and a tuxedo. ¯\_(ツ)_/¯

Shawl lapel tuxedo—Atelier Munro [you have to be measured in one of their local stores to buy one and customize it with a shawl lapel but here is the link]. Or buy one RTW from Spier & Mackay (mine is midnight navy with black satin facing on the lapels but this one is all black)

Black Watch tartan shirt—Proper Cloth [MUSINGS10 gets you 10% off]

Antoniella scarf [use code MUSINGS10 for an exclusive discount for my readers]

Black suede Belgian loafers—Myrqvist

Tuesday, Jan. 14 Pitti Day 1 Fit + Night

Photo by Joshua of Monogram Styling

First full day of Pitti I was like “sweater + tweed worker jacket will be a great, utilitarian look!” and I was basically cold all day. So I swapped in a coat that night.

Green mockneck sweater—SNS Herning’s Fisherman sweater has a similar vibe

Boltey Harris Tweed worker jacket

Selvedge Denim—Imogene + Willie “Henry” Fit (what I’m wearing) but also consider Gustin’s straight fit (err on sizing up with these)

Brown suede belt—Goldfels’ is great | Berg & Berg is good

Myrqvist dark brown suede chukkas

Longines Flagship Heritage Gilt Dial

At night I added my Chiaia coat because I was frickin’ freezing + Drake’s scarf

Gray Herringbone Eidos Chiaia Coat—This post has current links to the most similar coats

Scarf—Antoniella silk/wool Firenze scarf [MUSINGS10 gets you 10% off]

Wednesday, Jan. 15 Pitti Day 2 Fit

Day 2 I got smarter, and wore a sweater + coat and scarf. The winds died down a bit so I wasn’t cold.

Gray Herringbone Eidos Chiaia Coat—This post has current links to the most similar coats

Blue Breton stripe shirt—Saint James | Bronson (not the same navy tonal color but close)

Inis Meain pub jacket

Antoniella Solis Scarf [MUSINGS10 gets you 10% off]

Off-White Jeans—Natalino | APC | NN07 | FRAME

TLB Mallorca Artista loafers—Skolyx | TLBMallorca.com

Longines Flagship Heritage Gilt Dial

Wednesday Night Black Tie Fit

Photo by Erik Mannby

This is basically my default black tie rig. Instead of a pleated or bib-front shirt, I prefer a simpler broadcloth with covered placket. I need to get some patent opera pumps at some point.

Tuxedo—Spier & Mackay Black shawl lapel | Spier & Mackay Midnight navy peak lapel | ProperCloth Midnight navy [MUSINGS10 gets you 10% off your first order]

White covered placket shirt—ProperCloth in Thomas Mason luxury broadcloth (customize it with a covered placket) [MUSINGS10 gets you 10% off your first order]

Negroni Time cufflinks—Tyler & Tyler

Black suede belgian loafers—Myrqvist

Longines Dolce Vita automatic watch

Thursday, Jan. 16 Pitti Day 3 Fit

Photo by Christian Webster

In advance of Pitti I was thinking of buying this sportcoat from Natalino, so I DM’d them and asked if they’d just bring it to Pitti instead of having to ship it to me. It was sunny enough out that this was warm enough (I put the cashmere sweater on as a layer underneath for the evening, and had it in my bag to drape over my shoulders to the warmth during the day).

Natalino gray-navy-green gun club sportcoat

Navy cashmere crewneck—Spier & Mackay

Green bengal stripe shirt—Proper Cloth [MUSINGS10 for 10% off; use the Roma cutaway collar for closest design]

Spier & Mackay cream cotton-cashmere trousers

Myrqvist dark brown suede chukkas

Longines Flagship Heritage Gilt Dial

Gray Herringbone Eidos Chiaia Coat—This post has current links to the most similar coats

Friday, Jan. 17 MFW Day 1 Fit

Photo by Joshua of Monogram Styling

For the Cucinelli event on Friday afternoon, I pulled out the flannel chalkstripe suit that Spier & Mackay made for me. It’s a Marling & Evans cloth. The details on this suit are: wide vintage DB lapel, lighter-weight full-canvas make (2 layers vs 3 layers of canvas inside), natural shoulder with rollino. For the trousers, I did a single forward pleat with a 2-inch cuff. Once I got it, I actually moved the bottom 4 buttons slightly wider on the front. They felt a little too narrow to me.

Spier & Mackay MTM suit from Marling & Evans chalkstripe flannel suit—A ready-to-wear version is on sale

ProperCloth denim shirt [MUSINGS10 for 10% off your first order]

TLB Mallorca Artista loafers—Skolyx | TLBMallorca.com

Longines Flagship Heritage Gilt Dial

Saturday Night, Jan. 20 Personal Day

I didn’t do any work Saturday, and Saturday evening some personal friends spent some time with us. I wore the chalkstripe jacket but styled it with the cream Spier & Mackay trousers and the Antoniella scarf.

Spier & Mackay MTM suit from Marling & Evans chalkstripe flannel suit—A ready-to-wear version is on sale

Proper Cloth Thomas Mason goldline end-on-end shirt [MUSINGS10 gets you 10% off your first order]

Spier & Mackay cream cotton-cashmere trousers

Antoniella Solis Scarf [MUSINGS10 gets you 10% off]

Myrqvist dark brown suede chukkas

Longines Flagship Heritage Gilt Dial

Sunday, Jan. 19 MFW Day 3 Fit

Photo by Joshua of Monogram Styling

For the final day in Milan, there was a lot of walking.

Gray Herringbone Eidos Chiaia Coat—This post has current links to the most similar coats

Natalino gray-navy-green gun club sportcoat

Selvedge denim—Imogene + Willie “Henry” Fit (what I’m wearing) but also consider Gustin’s straight fit (err on sizing up with these)

Brown suede belt—Goldfels’ is great | Berg & Berg is good

TLB Mallorca Artista loafers—Skolyx | TLBMallorca.com

Longines Flagship Heritage Gilt Dial

Filson tote

Everything I Packed

Coats

Gray Herringbone Eidos Chiaia Coat—This post has current links to the most similar coats

Blazers & Suits & Chore Coats

Boltey Harris Tweed worker jacket

Natalino gray-navy-green gun club sportcoat

Spier & Mackay MTM suit from Marling & Evans chalkstripe flannel suit—A ready-to-wear version is on sale

Midnight navy shawl lapel tuxedo—Spier & Mackay Black shawl lapel | Spier & Mackay Midnight navy peak lapel | ProperCloth Midnight navy [MUSINGS10 gets you 10% off your first order]

Sweaters

Navy cashmere sweater—Cavour

Green mockneck sweater—SNS Herning’s Fisherman sweater has a similar vibe

Inis Meain pub jacket

Shirts

Black long-sleeve polo—Spier & Mackay

Black Watch tartan shirt—Proper Cloth [MUSINGS10 gets you 10% off]

Blue Breton stripe shirt—Saint James | Bronson (not the same navy tonal color but it’s a breton)

White covered placket shirt—ProperCloth in Thomas Mason luxury broadcloth (customize it with a covered placket) [MUSINGS10 gets you 10% off your first order]

Green bengal stripe shirt—Proper Cloth [MUSINGS10 for 10% off; use the Roma cutaway collar for closest design]

ProperCloth denim shirt [MUSINGS10 for 10% off your first order]

Pants

Fatigue pants (in either army green or khaki) from Proper Cloth [MUSINGS10 gets you 10% off your first order]

Selvedge denim—Imogene + Willie “Henry” Fit (what I’m wearing) but also consider Gustin’s straight fit (err on sizing up with these)

Spier & Mackay cream cotton-cashmere trousers

Off-White Jeans—Natalino | APC | NN07 | FRAME

Shoes

TLB Mallorca Artista loafers—Skolyx | TLBMallorca.com

Myrqvist dark brown suede chukkas

Black suede belgian loafers—Myrqvist

Accessories

Scarf—Antoniella silk/wool Firenze scarf [MUSINGS10 gets you 10% off] or Any Drake’s Scarf

Antoniella Solis Scarf [MUSINGS10 gets you 10% off]

Negroni Time cufflinks—Tyler & Tyler

Longines Flagship Heritage Gilt Dial

Longines Dolce Vita automatic watch

Filson tote (mine is the open top that maybe doesn’t exist anymore. Having a zipper on it would probably be useful, though I like how easy it is to reach into without a zipper)

Camera

Canon EOS R8 (Canon’s cheapest full frame mirrorless body. It was awesome in the fast-paced street style scenarios I used it and did very well with indoor high-ISO situations)

Lenses

Canon EF 70-200mm f/4 with RF adapter

Canon RF 50mm f/1.8

Canon RF 35mm f/1.8

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Comments2

  1. Looking good! I thought your choice of the navy flannel chalk stripe suit with the washed denim shirt was especially Pitti appropriate. In a Cucunelli style, maybe try the exact same look(with chalk stripe jacket, denim shirt and suede loafers) but with white or cream jeans?

    1. Thanks Gus!
      Actually I did exactly that the next day (which I didn’t post photos from). Personal friends of mine from Australia/New Zealand happened to be in France, and drove down to Milan on Saturday to come to church services there (the local congregation asked me to give the sermon—not in Italian thankfully!). I wore the full suit for services, but then in the evening we (Joshua from Monogram Styling who I was staying and working with) took them to a few places in the city to make an impression on their daughter (age 12, she is interested in fashion)—Dolce & Gabbana, Dior, Louis Vuitton—plus the Galleria & Duomo. For the evening I swapped out to the cream trousers I wore Thursday in the pics above. But I did not get photos except mirror selfies. Maybe I’ll put that in the post now that I mention it!

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