What to Wear in Madrid in October: A Houndstooth Blazer and Jeans

BLAZER: ZARA OVERSIZED DOUBLE-BREASTED BLAZER, WEARING THE XS FROM 3 YEARS AGO, THEY HAVE IT EVERY YEAR, IT’S THAT GOOD, I JUST GO THE BLACK/WHITE CHECKERED ONE THAT IS 42% OFF IN A SIZE S FOR A MORE RELAXED FIT (ALSO LOVING THIS MANGO BLAZER STRAIGHT BLAZER WITH FLAP POCKETS) | T-SHIRT: J.CREW BOYFRIEND JERSEY RELAXED CROPPED T-SHIRT | JEANS: AYR THE LALA JEANS | LOAFERS | BELT: REVERSIBLE BELT VIA AMAZON | SUNGLASSES: THE MOSANANA OVERSIZED ROUND CAT EYE SUNGLASSES THAT I WEAR NONSTOP ARE $15, ALSO VIA AMAZON.

If you’re packing for Madrid in October, my advice is to keep it simple but never boring. The days are still sunny and mild, while mornings and evenings bring just enough chill to want a layer, and a blazer is the perfect answer. This double-breasted houndstooth one is my current favorite. The black and white pattern adds interest without feeling loud, the relaxed, slightly oversized fit looks effortless, and the structured shoulders give an outfit instant polish. Pushed-up sleeves keep it feeling casual and lived-in rather than stiff.

The rest of the look is as easy as it gets: a classic white tee and my favorite straight-leg jeans. That’s it. A pattern-forward blazer does all the work, so everything else can stay quiet. Add oversized black sunglasses and gold earrings for a finishing touch, and you’re ready for a day of museums, long lunches, and wandering through the city. It’s a formula I come back to again and again because it’s comfortable, easy to repeat, and works for just about everything on your fall calendar. If you only pack one blazer, make it one with a little personality.

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