It’s always a little sad to pack away my summer clothes. It’s kind of a soothing ritual from my childhood; a way to positively transition from the warmer seasons to the colder ones. There’s a certain melancholy and nostalgia that goes with putting away bright beach clothing and unpacking darker, heavier winter pieces. But then, suddenly things don’t seem so bad when I pull out a pair of boots I almost forgot about or a sweater I can’t wait to cozy up in. It’s almost like getting a whole new wardrobe.
There are certain pieces of clothing that I wear year-round: button up shirts for work, blazers, and my black skinny jeans. Often I find that (despite how many how-to articles I read) transitioning summer dresses to winter can be hard, if not impossible. Most of my summer dresses are too beachy and casual, and just wouldn’t look right in winter. This dress - since it’s in black and white, colors that don’t scream summer - is an exception.It works in July, and with the right layers, it’ll work in November too. Here are three looks (with the same dress) to transition into fall: for work, for meeting up with friends, and for lounging around on the weekend (or heading to brunch!).
Work Smart: the blazer, the heels, the pulled-back hair/loose bun all say I mean business.
I’m slightly obsessed with these heels… they go with everything, and the cut-out design toughens up the half bootie/half sandal style. The key to wearing pants with a dress is going with heels, rather than flats. I tried on this look with flats - not so flattering! - heels make it appear intentional rather than, I couldn’t decide whether I wanted to wear a dress or pants, so I just threw on both… Other tips: Make sure your pants have a skinny fit, almost like tights, to contrast the shape of the dress. Black is always a good color choice!
Brooklyn Cool: the faux leather jacket, the ankle boots, the purposely undone/bed head hair, plus the pop of color in the accessories all give the dress an edgy, urban feel.
Beachy Casual: Romantic hair (extra points for braids!), unfussy, surf-style jewelry, and slip-on shoes equal the perfect balance of sexy and laid-back.
So there you have the three looks. We shot them by 69th street pier in Brooklyn - it was so much fun, with beautiful weather, although I left with several mosquito bites as souvenirs… I hope you get some inspiration from them (the looks above, not the mosquito bites). As always, thank you for reading!
Photographs by Tom Schelling.