After Living in NYC for 10 Years, I'll Never Make These Fashion Mistakes Again

Seemingly overnight, I became a New YorkerIn 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.

But there are also some great moments: attending your first NYFW show, scoring big at a sample sale, and finally landing your dream job. I like to think I learned a few things over these years of trials and tribulations, but at the very least, I’m sure I’ll never make these fashion mistakes again.

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.

1/23

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

3/23

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.

4/23

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

5/23

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. 

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. 

7/23

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

8/23

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.

9/23

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

10/23

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.

11/23

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.

12/23

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

13/23

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.

14/23

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

15/23

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.

16/23

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

17/23

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

18/23

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

19/23

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.

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.

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.

22/23

It never hurts to come prepared with a conversation piece. 

23/23

Or you can make a statement without saying a word. 

Up next: three fashion blunders that are low-key aging you.

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