Photos of second grader Arlo Weiner have been circulating around the fashion blogosphere. The son of Matt Weiner — creator of the awesomely written, amazingly art directed 1960s period TV series Mad Men — has adopted his very own eclectic, elegant style. Referencing many influences and periods he never experienced personally, this 8-year-old shows a creative flair for dress that is both daring and inspiring.

Some fun facts about Milo:

  • He requested a top hat at age 3 (I myself was an ancient 29 when I got my vintage pop-out top hat).
  • He loves ascots (who doesn’t?).
  • He likes to mix and match patterns and stripes.

Allow me to share some of my favorite Arlo ensembles:

Doesn’t he look like he’s going off to the office in a newsroom?


Arlo in fedora


Cary Grant as a spineless (but hilarious) reporter in His Girl Friday (1940)

Cary Grant as a spineless (but hilarious) reporter in His Girl Friday (1940)

This one reminds me of the Mad Hatter costume I wore last Halloween (I wore my own vintage pop-up hat):


Arlo in top hat

the Mad Hatter, Sir John Tenniel’s illustration of Alice in Wonderland

I love red on red on red too:


Arlo in red velvet 


I call this outfit Arlo’s 1890s inspired steampunk look:


Arlo’s steampunk look

Steampunk woman with goggles and cane


Arlo admits most of his ties are clip-ons which I cannot condone, though considering his youth I suppose I’ll let it slide. (Friends know I’m a tie snob all around — I only wear full Windsors myself.) I’ve joked for years about how my children are going to hate me for the suits and sailor outfits I’ll put them in; it’s comforting to know there are actually young people who choose to wear what many adults would consider outlandish. It gives me such joy to know there are parents who don’t shove Baby GAP down their childrens’ throats. Arlo reminded me that children are inherently creative, exploring a world they have not grasped all the rules of yet, perhaps giving them greater breadth of imagination than many adults, as they find what’s pleasing to themselves and not what they’ve been told is cool or fashionable or trendy.

Flashback to my own youth: I was raised on yard sales and hand-me-downs, which, being a child of the opulent, label conscious and snobbish 80’s, I lamented and resented daily. Seriously, I cried almost every morning as my mother forced me into layers of distinctly unattractive turtlenecks, stretched out tights held up by belts, and courderoys that were the antithesis of then-cool shiny spandex leggings (courderoys, that is, only on gym days at school — I was only allowed to wear skirts and dresses the rest of the days. And I attended public school!). But my mom redeemed herself at playtime. In the back hall we had a dress-up box (that grew over the years) filled with random flea market finds like reams of fabric and lace, tutus, hats, and clothes of all sorts that were either not in good enough shape to wear in “real life,” or were too big, or just too crazy. But my friends and I could entertain ourselves for hours with the contents of those boxes, wrapping the cloth around ourselves and assuming exotic identities, exploring the roles we might or might not actually appropriate later in life. And even though I now live in one of the fashion capitals of the world, I’m economically independent and can wear whatever I damn please, I actually choose to shop at secondhand and thrift shops still. And instead of waiting for the weekend to play in my dress-up box, I play dress-up every day, allowing my mood and creativity (not fleeting trends) to dictate what facet of my personality I choose to display. I hope young Arlo’s passion for dress brings him as much pleasure as mine continues to for me.