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Welcome back to InsideHook’s weekly deep dive into the best new menswear, where Paolo Sandoval, editor of The Stitch email, curates his favorite drops. With dozens, if not hundreds, of new apparel, footwear and accessory releases from our favorite brands to sort through, Paolo’s done the hard work and winnowed things down to the absolutely need-to-know style, watch and grooming drops that you can’t afford to miss.
This week’s haul: Todd Snyder’s Amalfi-ready vacationwear includes an excellent printed shirt, On and Loewe collab on a high-tech racer, Chris Black-founded Hanover releases made-in-America jeans and The Row debuts a sumptuous slipper.
The Best New Menswear Drops: Week of May 18, 2026
- The Proper Holiday Shirt: Todd Snyder Capri Polka Dot Shirt, $228
- The High-Tech Team-Up: On x Loewe LightSpray Cloudmonster, $990
- The All-American Jeans: Hanover Wander Jeans, $165
- The Brickstop Overshirt: Eighteen East Full Zip Caleb Shirt, $188
- The Suede House Slippers: The Row Casa Suede Slippers, $1,050
- More Menswear Drops
Todd Snyder Capri Polka Dot Shirt
Just imagine this printed Todd shirt paired with some white shorts and a spritz in your hand.
On x Loewe LightSpray Cloudmonster
For the latest installment of their ongoing partnership, Loewe retouched On’s new, 3D-printed Cloudmonster.
Hanover Wander Jeans
A dark wash, wide-leg jean made in America from deadstock Cone Mills denim, all for under $165? This feels like a scam…
Eighteen East Full Zip Caleb Shirt
NYC-based Eighteen East lovingly refers to the fabric used for this front-zip shirt as “Brickstop.”
Boggi x FIFA World Cup 2026 Winner Nations Polo
What better way to prepare for the upcoming world cup than with a swanky new summer polo?
Folk Lunar Linen-Cotton Suit Trousers
Pair with the matching blazer and you’ve got your summer wedding attire sorted.
Small Talk Studio Diamond Cutout Baggy Jean Shorts
Made in L.A. and cut from a stone-washed, 13.5-ounce selvedge denim, these relaxed jorts are a galaxy-brain addition to any summer wardrobe.
Bottega Veneta Tarik Intrecciato Leather Slides
The woven “Intrecciato” leather in these Bottega slides is also used in the brand’s highly coveted bags.
Sunspel Sea Island Cotton Riviera Polo Shirt
Casino Royale put Sunspel’s Riviera Polo on the map. Twenty years later, the trim, Bond-endorsed shirt gets a limited-edition version in Sea Island cotton.
Todd Snyder 5″ Seersucker Montauk Swim Trunk
Summer is almost here. Do you know where your trunks are?
Adidas x Wales Bonner Gazelle Snake Embossed Sneaker
Who would’ve guessed…yet another Wales Bonner Adidas banger. This time, the Gazelle is treated to a scaly makeover.
Banana Republic Italian Plaid Cotton-Linen Blazer
Soft through the shoulders and incredibly lightweight, this vintage-inspired Banana blazer is exactly what you should be slipping over a tee this summer.
Community of Lovers Hemp Pant
Swap in your sweats for these hemp-cotton trousers from Community of Lovers.
Polo Ralph Lauren Classic Fit Peace Love Polo Shirt
This PRL polo is aggressively summery. That’s the whole point.
Pompeii Mido Trainer
Prepare to see Spanish sneaker brand Pompeii everywhere this summer. With a trendy torpedo shape, vintage detailing and a sub-$200 price tag, they’re virtually unbeatable as a daily beater.
James Coward x Sanders Leather Banana Shoe
Canadian label James Coward frequently crops up on lists of up-and-coming menswear designers, and the brand’s recent collaboration with heritage shoemakers Sanders, a funky leather dress shoe with a banana-style lacing system, is the perfect example of why.
Drake’s Herringbone Cotton Artist Chore Jacket
With a mandarin collar and pankou closures, Drake’s recent take on the herringbone chore coat is more refined than rugged.
Our Legacy Rig Chinos
Our Legacy continues to push the envelope when it comes to accessible high fashion. Their latest innovation? A new “Octo Wash” piece-dying technique.
Manresa Ram Island Shorts
These slubby, Japanese cotton-linen shorts from New England-based indie label Manresa — complete with a half-elasticated waist and perfect “ube” colorway — are the newest Baggie killers on the block.
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