What’s crazier - wearing boots when it’s 90 degrees outside or wearing flip flops on the grimy streets of NYC?
As much as I love living in New York, there are certain city styles that I’ve fought. One being wearing boots - even ankles boots - any time after March. No, no, no! In my mind, spring is about breaking out ballet flats and TOMS and finally not freezing my toes off. Yet I see women wearing ankle boots well into the scorching days of August.
Then there’s the whole flip flop issue. I’ve read a multitude of blog posts (and the comments that follow) about how no “true New Yorker” wears flip flops, i.e. the streets of NYC are too filthy to wear shoes that flimsy (ah, people still wear SANDALS, don’t they?!) and that flip flops aren’t trendy. I’m not about to walk around barefoot in New York, but if worn right, flip flops absolutely can be trendy. They’re not just for the beach or a boat - they’re also for lazy days and casual nights out.
I must admit, as far as the whole “true New Yorker” thing, that I’m not a city native. I’m from Long Island. (Although I was actually born in Arlington, VA.) My identity, as much as I love it being deeply intertwined with my current Brooklyn dwelling, is truly as a beach girl. There is something about breezy beach-girl style that I fall into naturally, like the rhythm of a favorite song. It’s familiar. It just feels right: loose-fitting tank tops, relaxed shorts or a skirt and - yes - flip flops for day. At night, maybe I’ll wear a crop top, white jeans, and flat sandals, my hair wild and free, with a bit of sun marking my cheeks bronze. I’m truly at home by the water.
Each summer I’m lucky enough to spend a week at a beach house on Fire Island. Fire Island is like an exotic escape for me - but it’s only about 30 minutes from the mainland. No plane rides or cross-country traveling, no unfamiliar languages, no culture shock. You get there and immediately start to unwind. There are hardly any cars - everyone gets around by bike. As in, I ride my bike to get groceries from the local store - how quaint does that sound?! I wake up each morning and find my mom down by the water, drinking her morning coffee. (Is there anything more heavenly than a cup of coffee by the ocean before the beachgoers of the day have stepped foot on the sand?) My mom is more relaxed in those moments than she is at any other point throughout the year. She has talked about retiring to Fire Island. There are communities that stay over the winter months. I can see her living there very happily with Roger, her beloved wheaten terrier. (There they are running along the beach on Fire island below.)
Back to New York and ankle booties and flip flops in summer. I think it’s important to be open to the style of the area you live in. Why not adopt some of the trends you see around you, make them yours. But if you feel resistant to others - go with that too. In the end, style is not about proving something, but expressing yourself. Express who you want to be that day - go with what feels natural, follow your mood! If you don’t feel comfortable with your outfit, then it’s probably not for you - that works with trends and with most things in life.
As for ankle boots in spring, I caved. One rainy night last week, I was heading to get drinks at Botanica in NoLIta for a friend’s birthday. It was chilly outside and I knew I would be soaked, even with an umbrella. I put together a simple look: black top, white blazer, turquoise scarf, my favorite worn-in slim-fit jeans, a gold belt and booties that have gold sparkles by the heels. They make a satisfying “clock” with each step - a real stacked wooden heel! I have to say, boots were the best choice that night. But that’s what it takes to get me in ankle boots after March - cold and rainy.
As for avoiding flip flops all summer? That’s never going to happen - you’ll find me proudly sporting them, no matter what borough I’m in.
Here’s some summer footwear inspiration, whether you’re into ankle boots and flip flops year round, or just sometimes…
Flip flop tip: If you want to look as chic as humanly possible (and older than 16 - always an issue for me) in flip flops, stick to metallic colors, like silver (the leather J. Crew option at the top of the page is perfect for day to night) or the coppery gold pair below. Try to stay away from big decals or designs on the thong of the sandal. And leave super bright colored flippie floppies for the beach. These are Havaianas.
Heading out for a night of dancing by the beach? Of course you are. Slip on these charming sandals. You’ll get a bit of sexy height and you can still dance your butt off. They’re easy to pair with a sundress - or add them to your day look to dress it up. From American Eagle.
And these flats… just because they’re so pretty! From Zara.
Cut-out booties: These cute ones are perfect for those in-between, spring to summer months - where it’s still a little chilly. From DSW.
Full-coverage ankle boots: If you must wear boots (and sometimes the weather does call for it), go with ones in a light color - black can come off too heavy for the warmer months. And don’t forget to wear socks - your feet are going to sweat! These are from Zara.
P.S. Flip flops in the city - what do YOU say? Do or don’t? What about ankle boots in August - do you sport ‘em with pride or avoid them at all costs?