As a non-morning person and a New York mom now living in Italy, I found the idea of bringing my A-game to school drop-off daunting. I once read about an industry of NYC women renting clothes to keep up with drop-offs and pickups. My Italian father-in-law describes this as pure Americanata, or “over-the-top Americanness,” which is not always insulting (sometimes in pure admiration). Being a proud New Yorker and knowing many NYC parents, I knew this was an exception, not a rule. 

I’ve taken some trendy style tips from fellow moms in Italy for my own looks. Now, shopping for some other Italian-inspired school drop-off looks, including UGG slippers, a GAP lounge set, cat-eye sunglasses, and more, and they start at $20. 

Quince 100% Merino Wool Cropped Shirt Jacket

Quince

I’ve made wonderful friends since my daughter started school, and I can’t help but think of the luxe knit shirt jacket one of them wore in the first weeks of school drop-offs. It reminds me of Quince’s 100% Merino wool cropped shirt jacket, which is super soft and warm. The dropped shoulders give a slouchy yet elevated look, while the two chest pockets with buttons add even more style and functionality.

The best part? This Quince cropped shirt jacket is 74% off right now.

UGG Funkette Slipper

Amazon

From store windows styled with an Après-ski look to other moms like myself looking for comfortable options, the UGG Funkette Slippers are everywhere. The two-inch platform adds a great elevation and pairs well with wide-legged jeans. A strap on the back ensures the slippers stay put while you’re dropping off your kid. This pair comes in several colors, like chestnut, pink, black, and more. 

Andre Assous Olivia Studded Clogs

Bloomingdale’s

If you want to elevate the UGG look, check out these faux shearling-lined Andre Assous clogs. I’ve gotten tons of compliments from both sides of the Atlantic while wearing them. I wear them so much that they are the go-to shoes my toddler brings me when we’re getting ready to go outside. They’re easy to slip on and off when you’re running out of the house—something I’m inevitably doing at school drop-off time. They’re currently $100 off, too. 

Gap CashSoft Shaker-Stitch Crewneck Sweater

GAP

Italy is synonymous with fine cashmere, and sweatpant sets reach another level of elevation here. Plus, my husband owns a knitwear business, and I can confirm that cashmere sets like my Scaglione hybrid cashmere round neck and these joggers are very popular. The luxurious feel of loungewear is comfortable and practical for parents on the go, and you can get that feeling for under $50 at Gap right now. 

The brand’s “cashsoft” material is a soft cotton and nylon blend that feels like cashmere. The matching pants come in elegant black, statement-making neon pink, neutral taupe beige, and more colors. The high-waist, wide-leg, and shaker-stitch knit look pairs fabulously with a platform clog.

Calvin Klein Belted Faux Leather Trench Coat

Macy’s

This stunning Lafayette148 New York trench coat was on my holiday wish list this past year. However, I’m aware it’s definitely a splurge. A similar alternative is this beautiful Calvin Klein faux leather trench coat for thousands less. I love the cut below the knee, the belt look, and two side pockets to hold all your mom essentials. 

A trench coat like this is basically the school drop-off line that meets Milan Fashion Week. I could have my pajama top on—with yogurt stuck on it, naturally—and leggings and a trench coat with sunglasses, instantly turning into mommy and me at Milan’s front row. 

Ferragamo Prints 54MM Cat Eye Sunglasses

Saks Off 5th

No Italian school drop-off look is complete without a chic pair of sunglasses. These cat-eye sunglasses are my favorite for hiding tired eyes, especially when meeting other parents for an impromptu cappuccino after drop-off. Their geometrical shape adds a whimsical touch that will never go out of style. So, yes, the drop-off line can be a Fellini film and still give you 100% UV protection.

Mininai Chunky Oversized Scarf

Amazon

Starting in early fall, Italians are out in full force with scarves. While I love the functionality of a shawl, I sometimes want a more youthful approach to it, so I wear this fringe scarf during winter. You can score this look for just $20 on Amazon, too. The oversized scarf feels like cashmere and is large enough to wear as a shawl or a scarf. It comes in nearly 20 colors, too. 

Everlane The Rigid Way High Jean 

Everlane

Denim is a common choice for school drop-offs and pickups, and I’ve been deeply coveting the Everland Rigid Way-High Jeans. Rigid denim has beautiful longevity—it seems vintage and can last forever. These jeans feature a high-rise waist, straight leg, and slim fit through the hips and thighs. They also come in four washes: rich indigo, vintage light wash, paint splatter, and worn-in black (my favorite).

The Everlane Rigid Way-High Jeans are as low as $32 right now, depending on the wash selection. 

Zara Double Sided Short Jacket

Zara

I’m pretty sure I’ve seen this Zara cropped aviator on a fellow mom at school, and at this price point, I’m totally into trying it out. I love the chocolate brown shearling style, and the cropped style makes it feel more wearable inside and outside. It’s available in sizes XS to XXL, and the brand says the jacket runs large, giving you a stylish oversized look.

If you’re looking for a similar option at a lower price point, check out this aviator jacket on Amazon for just $51 when you use the on-site coupon.

Levi’s Faux Fur Lined Hooded Parka

Amazon

With classic outdoorsman styles trending, I have seen the rising popularity of this Woolrich parka. While it’s currently 40% off, the higher price tag is still a splurge, so I recommend this Levi’s parka that’s hundreds less (even with the 30% off coupon). It has several pockets, a faux fur lining, a removable hood, and more useful features. 

“I live in central Maine and was worried this wouldn’t be warm enough for the winter up in the mountains,” shared one Amazon shopper. “This jacket surprisingly works great, especially if you wear a light/medium sweater underneath.”

Kate Spade New York Detachable Cell Phone Lanyard

Amazon

I went from being a tiny purse girl to carrying a diaper bag and stroller, and I started seriously craving to carry less stuff. I was inspired to embrace a phone bracelet after seeing several moms at school drop-off wearing one. I bought this Kate Spade phone charm bracelet for when I want to carry the lightest load possible. 

Although, if you have important cards or your license, pair it with this Kate Spade leather magnetic phone wallet that attaches to your phone and through cases so you can mix and match looks. Plus, you’ll still be able to use the wallet through phone upgrades and size changes (an essential feature for me).

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