My brother-in-law does wine tastings. He swirls, he sniffs, he says things like “a little closed on the nose” about a £12 bottle, and everyone nods. I have never once understood what he means.
Then last week I spent forty minutes in front of the hall mirror trying to pick one baseball cap, and I finally got it. You can’t explain a cap. You can only describe it with total confidence and hope nobody asks follow-up questions.
So here’s the flight. Five Dsquared2 caps from The Designer Box, which currently has a whole headwear banner on its homepage, and every one of them marked down to the same £80. The original prices ranged from £150 to £265. Same pour, very different vintages.
No. 1: Icon Forever, White
Was £160. Now £80.
Nose: Clean laundry. Bright white cotton, curved peak, the ICON graphic across the front.
Palate: Easy. This is the house white. It goes with a grey hoodie, it goes with a navy coat, it goes with the face you make when you’re running late.
Finish: Short, and I mean that kindly. Buckle at the back, on your head, out the door.
Cellaring potential: Low. White caps pick up a grey tide line along the brim by November, and you know it.
No. 2: Ceresio 9, Black
Was £155. Now £80.
Named after the street the brand calls home in Milan, which is the kind of detail that lets you feel smug at the bus stop. Jet black cotton, a white logo print, and a narrower curved brim than the others in the flight.
That narrow brim is the whole story. It sits closer to the face and looks less like you’re about to coach a Little League team. Adjustable strap at the back. It’s also the newest one here, only added to the site last week.
My tasting note, written on a Post-it and stuck to the mirror: “serious.”
No. 3: Icon Tropical, White
Was £190. Now £80.
The rosé of the lineup, and I say that with love. White cotton with the logo printed in black, fuchsia pink and yellow, embroidered logo at the back, eyelets and silver-tone hardware.
Wrong season? Maybe. It is late September and this cap clearly thinks it’s somewhere with a pool. But £110 off is £110 off, and a bit of fuchsia under a camel coat is doing something I can’t fully defend but can’t stop looking at either.
No. 4: DSQ2 Maple Leaf, Black
Was £265. Now £80.
The big markdown of the night, close to 70% off. A baseball-style “dsq2” patch on the front and the Caten twins’ names embroidered on the back, which is a nice nod if you know the brand was started by twin brothers from Canada, and a mystery to everyone standing behind you in a queue.
Full-bodied. A sporty cap that still looks deliberate with a plain black jumper. If I’m being honest, this was the one I should have picked.
No. 5: Born in Canada DC64, Black
Was £150. Now £80.
The funky natural wine of the flight. Cotton gabardine with deliberate distressing, 3D embroidered DSQUARED2 lettering and “Born in Canada” on the front, “Caten Family” stitched on the back.
Some people will look at the frayed bits and ask if you’ve had it since school. You will have to be fine with that.
Dessert wine: ICON Beanie, Black
Was £185. Now £100.
Not technically a cap, but it’s the end of September and I’m not an idiot. 100% wool, made in Italy, with the Icon logo embroidered on the front. It sits at the end of the tasting because it’s the one you’ll actually be wearing in January when all the caps are hanging on a hook.
What I ordered
The Ceresio 9. I stood in the hallway with the Maple Leaf in one browser tab and the Ceresio in the other, and the narrow brim won. My partner said the Maple Leaf was “more fun.” My partner also owns a hat with a propeller on it.
Corkage (the boring but useful part)
- Delivery to the UK and the US is free on every order right now, no minimum spend. Order before 3pm and it’s dispatched the next day.
- There’s a 14-day returns window, which is useful when a cap looks different on your actual head than it did on your phone.
- The shop says all its stock is brand new and authentic, from suppliers it vets itself. It also takes Klarna and Clearpay if you’d rather split it.
- These are one-size caps with a single listing each, so when one goes, it goes. The site-wide sale runs up to 75% off select products, if you want to wander beyond the hat rack.
If you’d like to do your own tasting, the Dsquared2 caps are here at The Designer Box. That’s an affiliate link, so I may earn a small commission if you buy, at no extra cost to you.
My brother-in-law, for the record, thinks all five are “a bit much.” He was drinking a £12 bottle at the time.