the loopiest paintings italy has to offer


In a flimsy attempt to make my holiday a tax deductible business trip, here are some of my favourite paintings I saw while I was on holiday.

Because - and I’ve literally only just realised this?? - I simply love stomping around a city and looking at loopy paintings. This might be obvious to some of you who watch me do exactly this every Friday on my silly little gallery days, but this is brand new information to me !!! I DISCOVERED a fun fact about myself. I just love art! !!! I love batshit crazy paintings!!!! I love having a lil look at an image and thinking about what it does, learning about the person that painted it, love having a lil think or a chat about what holds energy within the image. Can’t believe I’ve been an art critic for 7 years nearly, and I’ve only just clocked on that I LIKE ART.

Now, listen yeah. Not only do I like art. I’ve always loved the Sienese school. The story is: Wayyyyyy back in like 13/14th Century Italy, painters were having a crazy wild time. It was like the end of medieval times (nearly), the Renaissance was just about to happen. in terms of what was actually being painted, things were looking Gothic & Byzantine a bit. But none of them knew that ofc. They were just doing their best and having a lovely time. But now looking back - Siena & Florence were buzzing with good art vibes. Perspective was about to be invented. Painters were still figuring out how much they could cram into the gentle limit of their canvas. They were trying to tell a story: any story, about christ, about saints, about their patrons and their city and their lives. They were trying to crowbar as much as possible into these little spaces on the side panels of altarpieces, in the little flourishes and the margins. They didn’t have a convention for how space should be configure - perspective wasn’t an established science yet - space was still liquid and malleable plastic.

As a result, those paintings are loopy as hell. And I love a loopy painting. I love the Sienese school!!!! I remember seeing them in one of those big fat coffee table books when I was a teenager, and they made me laugh - but then when I looked closer, they made my brain go pop. i hold them close to my heart because they make my eyes feel fizzy and they make my chest flush hot. They feel like an incredible secret because when you think about important Italian paintings, you think about those big boys in Florence. But the paintings produced by the Sienese school have got this weird position in art history.

When Vasari wrote Lives of the Artists, yeah he was writing the first lil text of the grand & winding art historical canon. But he was also a painter from Florence with hometown pride. So he wrote about how sick Florence’s artists were. He wrote about them like they were the vanguard, the edgiest bitches out there. He wrote about them sooooo well that we all think it was them alone that revolutionised European painting. Turns out the boys in Siena were doing loopier things. And maybe history remembers things in a straight line! Maybe life and image genealogy isn’t that neat n tidy. And maybe also energy isn’t that easily contained into a series of logical straightforward events. Siena has got talent and masterpieces and not as many queues to go see them lmao.

But yes, went to Italy to look at loopy paintings, eat gelato, drink aperol and stomp around some little cities. Had a lovely time! Ate so much cacio pepe I’m now convinced my lactose intolerance has been cured. I stomp stomp stomped around galleries, churches, monasteries, piazzas; here’s the best of what I saw.

1: The Blessed Agostino Novello Triptych // Simone Martini

Silly of me to start with this one bc I actually can’t write too much about this here (pls wait for next Sunday, thank you for your patience). But I can’t not start with it, because the panel with St Agostino swooping down to catch the child falling from the balcony »»

Wait, a better pic from google:::

that panel is my favourite painting in the entire world. Ever. My top number one of all time. Best thing I’ve ever seen. Want to get it tattooed on my back so I can carry it around with me. Ayyyy I love it. I’ll tell you why next Sunday shhhhh.

2: Maesta // Duccio

If I was committed to telling you art historical fun facts, I’d say that this painting is the most important painting in Italy and I’d tell you why. I don’t care too much about the why though. IRL this painting had like a crackling energy. Dark room and hushed voices, it is enormous and impressive and intimately teeny tiny all at the same time. Duccio painted this when he was well established as Siena’s foremost talent. Back in the 1300s, when this painting was finished, it was paraded through the streets of Siena - from the artist’s workshop to the cathedral it was made for. People followed the procession with candles. The shops closed and people who lived on the procession route hung lovely silks from their balconies. Imagine: you’re a resident of the city-state of Siena in the 1300s. You don’t see images like that. The world just unfolds before you. There’s no internet, no instagram, no photography. Paintings are rare and special. They are in important buildings like the church and the public buildings from which your state is governed. Then this 6 by 6 meter masterpiece, in dazzling gold, lurid colour - christ, madonna and all the saints - it travels past your front door. I think it’d make my brain melt. i think I’d lose my mind. Idk- I think I mostly like the story around this painting. I like the idea that a painting could mean so much for a city that the people of the city would willingly parade it through the streets. I like the idea of a painting being exhaled in that way. It feels sweet, special, emotional. I also like the painting itself. The scenes from the passion on the back of the maesta are beautiful, bonkers, vibey as hell. They do this weird twisting turning thing with the space. I think that’s where the art historical importance is, but it’s also where the energy is. On the back, always on the back.

3: Madonna del Latte // Ambrogio Lorenzetti

On its own, this is just a beautiful painting. But there was something about the scale of it in the big church: the grandeur felt so baggy around it. It felt so small and intimate and handheld. Portable?? Idk. Both virgin & child are looking out at the viewer, Christ’s hand is squeezing his mum’s bare tit. Her front hand flattens out into long terrifying spindly fingers. This thing has got energy for me - BIG TIME. I like the way the figures feel staticky - like if you touch them they’d zap you. I like the confidence this has in its unfaltering gaze. I like the way their fleshy faces feel rosy and warm. The way Christ’s foot is pushing his mum’s arm out and away, but also pushing out at us. It pulls me in a tells me to fuck off. I love it!!!!!!

4: Madonna dei francescani // Duccio

This painting is so small. It’s barely the size of an airport paperback. It is teeny tiny. I was inches - INCHES!!! - away from it in the gallery. My nose was basically brushing against the glass. It is beautiful and ruined. The madonna’s face and the grimacing faces of the worshippers at her feet are the only things left in clarity. Her robes tumble down to her feet like an expanse threatening to engulf them & us. The angels holding up the sheet behind her are crumby but they still push her out, swallow up the rest of the remaining space. It’s a really dizzying painting because it is so small and it sucks you in. The space is just a myth. It’s a vacuum imo. Just not there even though it should be.

5: The Madonna appears to Pope Calixtus III (Maria asks for help for the city of Siena in the famine of 1455) // Sano di Pietro

I just like the way scale has been warped in this painting. It feels like a dream or like a surrealist masterpiece. It feels like fiction. Silly! Kinda whimsical. But then also deadly serious - important but energetic

6: city on the sea // Stefano di Giovanni

Crazy!!!!! I hope you can see it through the glare. This is just a really good painting of a city by the sea, but space is simply a dissolving myth around the hinges of each angle. It makes me feel woozy —— I LOVE it.

7: Adoration of the Magi // Lorenzo Monaco

This wasn’t in Siena, this was in the Ufizzi in Florence, but !!!! I think it’s a painting from the Sienese school? I love the way the space bends around the figures, the way the composition feels like the land is gathering up to cocoon the scene. I like the faces, the expressions, I like the way architecture is rendered. I like this painting!!!


I think after traipsing round looking at endless altarpieces, I really noticed that the margins and side panels was a space where artists could go a bit nuts. Because if the main panel is for Jesus / Mary, the crucifixion, annunciation, resurrection, christ the redeemer - only so much you can do with that space. But the MARGINS!!! Artists could really do whatever there. So here are my favourite little obscure scenes from the snippets, the predellas, the margins and side panels.


This goopy chewing gum pink painting of San Bernardino in piazza del Campo by San di Pietro

That’s all!!! Longest blog I’ve ever written whewwww. god bless u for making it this far, maybe u deserve a lil emoji game treat for the ig comments as a congrats for ur endurance. soooooo is u made it this far whack a 🍦 lil ice cream emoji 🍦 in the ig comments on today’s post about this blog/the paintings. & stay tuned for more painting thoughts next Sunday & bye xxxxxxx