After a Decade in NYC, I'll Never Make These Fashion Mistakes Again

Updated 05/07/19
New York Girl Style

Seemingly overnight, I became a New Yorker. In reality, this moment has been years in the making—10 years, if we go by popular consensus—but as of 2019, I will have lived in New York City for a decade. For those of us who aren’t born and bred New Yorkers, there are several rites of passage one must encounter before earning this coveted merit badge:

Live in a mouse-infested apartment? Check.
Walk 20+ blocks in four-inch heels because you can’t get a cab? Check.
Accidentally get on the express train and end up in Queens? Check.

Accumulating a Closet Full of Saturday-Night Outfits

Reality check: Even though you might live in New York City, odds are it’s a weekday. After accumulating a few too many sparkly going-out tops and random cocktail dresses, it became clear that my wardrobe was prioritizing nights out in the Meatpacking District instead of, well, the mundanity of Midtown. Now that I have a more responsible schedule, I love the idea of a capsule wardrobe. Some great basics, a little black dress or two, and of course some pumps with personality.

Equipment Slim Signature Silk Shirt $214

You can't go wrong with a button-down. 

Rag & Bone Ophelia Asymmetric Stretch-Knit Midi Dress $375

One of those perfect day-to-night dresses. 

L.K.Bennett Tess Pumps $275

A favorite of Kate Middleton, these classic black heels are a must-have. 

Commuting in Uncomfortable Shoes

Speaking of shoes, remember Melanie Griffith’s character in Working Girl? She wore dad sneakers before they were cool. After taking the Staten Island Ferry to her office in lower Manhattan, she’d change into some killer ’80s heels. You, my friend, are also a working girl. You too will be commuting in all sorts of weather. Buy some dad sneakers if you like, or stick to these tried-and-true classics.

Women's Stella Mccartney Stan Smith Sneaker
Stella McCartney Stan Smith Sneakers $325

Stella McCartney's take on this Adidas classic features an eco upgrade with vegan leather.

'Arizona' White Birko-Flor Sandal
Birkenstock Arizona White Birko-Flor Sandals $100

If you insist on commuting in a sandal, Birkenstocks are your best bet—the arch support is a lifesaver when walking around the city in the summer. 

Cole Haan Grandexploer Genuine Shearling Trim Waterproof Hiker Boots $280

I'll be wearing these to and from the office all winter. 

Buying Something Just Because It's on Sale

On that note, if you can score a deal on those Balenciagas (the ones that look like socks!), go for it. Or not. I once bought a really gorgeous pair of Prada loafers that were 30% off and a half a size too small. I loved them in the store but hated them on my feet (see: commuting shoes). If you see something shiny on sale but it’s not your size, tell a friend instead of trying to make it work. 

Staud Nic Bag $395 $297

This bag is perfect for holiday parties and can be used for years to come. 

Diane von Furstenberg Mollo Booties $348 $244

DVF makes a quality shoe, and these on-sale booties let me dip my toes into the white boot trend without breaking the bank. 

Forgetting to Dry Clean Cashmere Sweaters

Real talk, I love a cashmere sweater. I would live in a cashmere lounge set if it were socially acceptable and seasonally appropriate. You know who else loves cashmere? Moths. And yes, moths live in Manhattan, too. Do your future self a kindness and dry clean your sweaters before you put them away for the summer. Trust me on this one.

Everlane Cashmere Waffle Square Turtleneck Sweater $155

I already own about seven Everlane sweaters and just added this one to my cart. 

Vince Shrunken Cashmere Sweater $295

Vince also makes wonderful knitwear. I love this season's cropped styles. 

Wearing the Wrong Size Bra

At some point growing up, you were probably gifted either Our Bodies, Ourselves or The Care and Keeping of You. One thing these books neglect to mention is that your body continues to change during that defining decade between 20 and 30. Whether you need (yes, need) a strapless bra for a particular dress or top, find yourself wanting a bit more support, or just want to treat yourself, make sure you’re buying a bra that fits you right now—not that fits you after you lose or gain weight—one that fits you today. It’s not something you can always see in a mirror, but you can definitely tell in photos. Note: This counts for sports bras, too.

Natori Bliss Perfection Underwire Contour Bra $62

When I find a great fitting bra, I always buy it in black and nude.

Hanging onto Outdated Denim

I spent a ridiculous amount of money on some bedazzled, low-rise jeans in college. That style is never coming back—and even if it was, I’ve aged out of it. Fortunately, several stores offer discounts when you bring in your old denim! I’ve traded in a few old pairs at Madewell and scored these much more appropriate styles for 20% off.

Madewell Curvy High Waist Skinny Jeans $128

The rise and the wash on these jeans are perfect for my shape and style. 

Madewell Cali Chewed Hem Demi Bootcut Jeans $128

The frayed hem on these jeans gets better after every wash. 

Sleeping in Worn-Out Pajamas

Have you ever woken up to a fire alarm and had to evacuate your apartment building at 3 a.m. in the winter? Then you’ll know pajamas with holes are not your friend. I love J.Crew's affordable sleep sets, and I’m dying to get my hands on a silk pair.

J.Crew Sweet Dreams Short Pajamas $80

This vintage-inspired sleep set is undeniably cute, but I still don't recommend getting locked out in your PJs. 

Nordstrom Moonlight Pajamas $65

Alternatively, if you get trapped inside your apartment, you could spend the whole weekend in these!

Forcing a Trend

I love to see what my Who What Wear colleagues wear to work every day, especially during NYFW. They are the best at mixing and matching prints and trends and colors. Myself, on the other hand? A stripe is about as wild as it gets—and if I’m feeling really crazy, I might even wear a color like navy! The truth is, my style is classic prep: button-down, jeans, loafers. But every New Yorker needs a leather jacket—I got mine at the five-year mark and wear it daily in the spring and fall.

Madewell Zip Top Transport Leather Tote $188

I've had this Madewell tote for literally 10 years. It was my first NYC work bag and it still looks great.

A.P.C. Niki Striped Cotton Top $135

It's impossible to have too many versions of the classic Breton-striped shirt. 

Iro Ashville Leather Biker Jacket $1205

Leather jackets only get better with wear and tear. Invest a little, and it will last a lifetime. 

Gucci Jordaan Leather Loafer $730

There's a reason every NYC girl has a pair of these classic loafers. 

Accidentally Flashing People on the Subway

Thank goodness for Bella Hadid who single-handedly brought back the biker short trend last summer. But actually—it was so hard to find cute biker shorts before then! No one wants to see (or be) a flasher on the subway, and that includes even those accidental ones. Wearing a dress on your commute? You’ll want to pair them with these.

Good American Icon High Waist Biker Shorts $65

If you know, you know. 

Forgetting a Swimsuit

One of the best parts about living in New York City is leaving the city. You never know who is going to have access to a rooftop pool, hot tub, or an open spot in their summer share house. Even if it’s cold—or winter—throw a swimsuit in your bag just in case.

L*Space Arizona Classic One Piece Swimsuit $165

Always be ready to make a splash. 

Underdressing for a Work Event

While the media industry tends to be pretty casual, there’s nothing worse than showing up in your everyday office attire when everyone else is showing off their street style chops. While my preferred emergency fix is a bold lip and a black pump (pairs nicely with a button-down and jeans!), I always try to gauge the fanciness of an event before attending. If you find it difficult to decode the differences among summer chic, dressy casual, and cocktail attire, it never hurts to overdress. Jewelry and accessories are an easy way to upgrade any look.

Shashi Unicorn Coin Necklace $50

It never hurts to come prepared with a conversation piece. 

Stella + Ruby Rainbow Statement Earrings $45

Or you can make a statement without saying a word. 

This post was originally published on our sister site, Who What Wear.

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