The Joy of Dressing a Boy

Photo by Tina Barney (1990)

Can't go wrong with classic staples

You often hear people gush about much fun it is to dress a little girl (and yes, it is an absolute delight!), but you don’t usually hear the same about dressing a boy. And I have to say I have found SUCH joy in dressing my boys.  To me, the key has been finding and investing in classic staples they will wear time and time again. Truly a uniform if you will. If you keep these stocked in their wardrobes they will always look pulled together. 

POLO SHIRTS – Lacoste are at the top of my list, particularly in Navy

STRIPED LONG SLEEVE TOPS – I live for these from Saint James 

SWEATPANTS – These from H&M and these from Zara fit well 

SHORTS – I love a shorter short with an elastic waistband and Cadets and Oso & Me make the very best, hands down

CASHMERE SWEATERS – You can never have too many Ralph Lauren cashmere sweaters, but I have found these from J.CREW are also great and half the price. Don’t worry about getting them dirty (seriously!) 

OUTERWEAR – Always the perfect polished finishing touch. My favorites are this Barn Jacket and this Patagonia vest

THE BLUE BLAZER – So iconic it needs it’s own category. Nothing more fitting for a special occasion and no one does it better than Ralph Lauren. I always hunt for these 2nd hand since they are pricey and quality is beautiful. 

PAJAMAS – These are both classic & comfortable 

SHOES – Can’t go wrong with New Balance, Cientas, Supergas or Vejas 


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