It’s one thing to hear about how New Yorkers have the cool and casual look down to a science, and another thing to see it in person! Pop culture has told us time and time again that there’s something special when it comes to New York style – from shows like Sex and the City to Gossip Girl, New York fashionistas have dominated our TV screens and magazines for decades. I was more than ready for the opportunity to see if the effortlessly chic looks that I grew up watching translated to real life – and I was not disappointed during our recent trip to NYC. Ready to learn how to nail the effortlessly cool New York City style? Let’s dig in!
1. oversized t-shirt + cardigan over the shoulders + jeans + mary jane flats
Shop a similar look: cardigan | oversized tee | flats | jeans
Fifth Avenue was a perfect place to scout New York street style – it’s one of the most famous (and expensive) hubs for designer boutiques and shops in the world. It’s a popular spot for visitors as well as locals shopping for their next favorite find. I spotted many of the brands that we love here at MCO, like Madewell, Banana Republic, and J.Crew.
This first look is the epitome of effortless, casual chic. Many of the looks I spotted were very understated – but the way that the pieces are styled elevates them, as well as the quality of the individual items. For instance, a basic white tee can go a long way. Choose an oversized version to balance out slim jeans, and tie a sweater around your shoulders for a practical and classic accessory. Mary Jane flats complete your look.
2. linen button-down + drawstring pants + sandals + tote bag
sandals | button-down | pants | tote bag | earrings
Beyond providing great inspiration for city street style, this list contains plenty of ideas for transitional fall looks as well. We may have been in New York as summer shifted into fall, but the temperatures were still in the 70s and 80s! If you live in a warm climate and are looking for fall-inspired looks, you’ve come to the right place.
One way to shift your summer linens into more appropriate fall wear is by deepening your color palette. This was a popular strategy in New York street style! For instance, swap out your crisp white button-down for a flax-colored or oatmeal shade instead. As for your pants, a breezy pair of drawstring pants will keep you cool and comfortable pounding the pavement. Leather sandals in cognac provide a new texture to your look, while still being weather-appropriate. A spacious black tote bag completes the look.
3. leather jacket + chambray shirt + plaid pants + sneakers
Shop a similar look: leather jacket | sneakers | plaid pants | chambray shirt | sunglasses
What gives off a cooler, edgier vibe than a leather jacket for fall? The leather jacket has endured decades of trends and changing styles. Whether you prefer a moto-style jacket similar to the one worn above, or maybe one with simpler lines like a bomber style, the leather jacket is a surefire way to add a bit of edge to your daily look.
New York women love to mix aesthetics to create a look that’s new and all their own. This outfit is a perfect example. The plaid pants and chambray shirt may feel more “business casual” on their own, but styled in the right way can create a cool look for a Saturday spent shopping. Add a pair of sneakers for another laidback touch.
4. sleeveless blazer + pleated skirt + pearl stud earrings + mary jane flats
pleated skirt | top | flats | tote bag | earrings
I explored New York for a full afternoon to check out the local street style, which meant that I was able to spot natives on their way to lunch and then on their way home in the evening. The work-appropriate looks were just as cool and effortless as the casual ones.
Need one guaranteed way to look put together without actually having to put much effort into your look? Try a monochromatic moment for your outfit’s base, such as a pleated skirt and sleeveless blazer in the same color. The theory here is that choosing a coordinating color for your top and bottom will make your outfit look intentional, even if you didn’t purchase it as a matching set. Add texture to make the look more interesting – the pleated skirt accomplishes that here!
5. striped button-down + classic jeans + ankle boots + leather belt
Shop a similar look: boots | button-down | jeans | bag | belt
I’m not ashamed to admit that I pretty much lived in striped button-down shirts this fall. I generally feel more comfortable in sleeves, but living in the Midwest makes that difficult during the hot, humid months. A breezy button-down is the perfect solution, and it made this small-town girl happy to see that big-city girls love the capsule wardrobe staple just as much as I do.
P.S. If you need more capsule wardrobe ideas, we’ve got you covered. MCO has a great library of resources and free fashion help for a timeless, staple collection that you can access here.
To make your favorite striped button-down more fall-forward, reach for your favorite pair of blue jeans. Crop styles and bootleg pairs seemed to be especially popular in NYC. I don’t blame New Yorkers – I wouldn’t want my jeans touching the ground either with how much walking they do. (Maybe it’s just the horror flashbacks I have of long jeans being soaked by snow in the winter!) Black leather ankle boots were a popular choice to pair with jeans – choose a pointed-toe version to help elongate the appearance of your leg for a flattering look.
6. oversized blazer + white tee + striped shorts + chunky sneakers
sneakers | blazer | shorts (similar) | socks | crossbody bag | earrings | tee
If you live in a warm climate, don’t feel like you have to put your shorts away even though fall is officially here. Style them in a seasonal way by pairing them with traditionally fall-appropriate pieces to complement them, like a navy blazer. The oversized blazer provides coverage on top and also adds a cool, elevated edge to your striped shorts. Slouchy socks, chunky sneakers, and a crossbody bag complete the look.
Related: How to Style Chic Fall Outfits in Warm Weather (& Outfit Ideas!)
7. chambray button-down + linen pants + tote bag + Boston clogs
Shop a similar look: clogs | wide-leg pants | shirt | tote bag
One of my favorite style tips from New York City fashionistas? Don’t be afraid to embrace oversized proportions to experiment with new outfit combinations! Some days, all you want is to feel comfortable, and there are ways to do that while also having fun with your favorite pieces. Try pairing a relaxed-fit pair of pants with a chambray button-down.
The key is to pay close attention to the little details that will help prevent you from looking like a little kid playing dress-up. One tip is to roll up the sleeves of your shirt. It doesn’t seem like it will make that big of a difference, but even just showing a little bit of extra skin and shape, like your forearms, helps to balance the oversized look. Also, consider a pair of pants that hits around your ankles. This little trick also goes a long way into making the outfit work.
8. white tee + utility pants + baseball cap + sneakers
hat | sneakers | t-shirt | shoulder bag | pants | sunglasses
If you haven’t caught on by now, a basic white tee is at the top of the essentials list when it comes to style tips from a New York fashionista. And if you need recommendations on where to find the perfect one, Carolyn’s got you covered! She tried eight of the most popular white tees on the market and ranked them for you.
Utility-style jeans or pants are another great piece to add a subtle edge to your look. I spotted them in numerous cool girl looks. They’re a great alternative to classic blue jeans, and come in nearly every color you could imagine. This outfit is completed by a few trending accessories such as Adidas sneakers, rectangular sunglasses, and a small shoulder bag.
9. oversized tote bag + fitted blazer + ankle boots + dark-wash jeans
Shop a similar look: kick-out jeans | ankle boots | blazer | oversized tote bag
On the opposite side of the spectrum of oversized looks, I also noticed many slim, fitted looks that were just as chic. You can’t go wrong with a pair of dark-wash jeans, especially in the fall. Although I would recommend staying away from rips if you’re building a classic wardrobe, a subtle raw hem is a great way to add a bit of edge if that’s the look you’re aiming for. As for shoes, once again, you can’t go wrong with a pair of ankle boots. Although a thin kitten heel might be trending, if you plan to walk a lot in them or wear them on your daily commute, you may want to choose a block heel instead.
There is one oversized component here – the tote bag! One of the most popular pieces I spotted time and time again was an oversized tote. It makes sense – many New York women leave the house in the morning and don’t make it back home until late in the evening hours. They need a bag that can accommodate their workday, a trip to the gym, and an evening cocktail hour with friends.
10. racerback tank + black jeans + chocolate brown sneakers + woven tote bag
sneakers | jeans | tank top | tote bag | earrings
Another one of my favorite style tips from New York fashionistas? Balance dressing for the weather and dressing for the season! As we’ve learned, sometimes that means harmonizing between two different looks. Here in the Midwest, we always seem to have a fall fakeout before the heat returns when September has already begun.
New Yorkers spend a lot of time outside, and it seems they’ve got this concept down pat. For instance, this look takes a summer piece (the racerback tank) but balances it against fall colors to create an outfit appropriate for warm weather that still feels appropriate for autumn. Chocolate brown and burgundy are two trending colors this fall, and they were everywhere in New York street style!
Lots to Learn from the Fashionistas of NYC
There’s a lot to be learned from The City That Never Sleeps! Beyond just the tips we’ve already covered, there’s an important one that I also need to note – confidence. Confidence is a key component to dressing well because even though the saying typically goes that “when you look good, you feel good”, the inverse is true as well! So, while you try to recreate some of the looks above, remember that fashion can be so much fun!
Want more ideas about how to look (and feel) good while getting dressed each day? Up Next: How to Look Good in Everything You Wear
