When I graduated with my MFA from Southern Illinois University in Carbondale, Illinois I shipped my stuff back to my parents East Coast basement, packed one rather large suitcase, made a pit stop in Chicago for a play reading, and headed to New York City to start my new job. I had my heart set on teaching college, but after thirty applications and no offers, I got a call from a large Manhattan-based theatre nonprofit who offered me a position I hadn’t even applied for. It was work. It was NYC. I’d be crashing at my friend Sarah’s Upper West Side studio. So, off I went.
I was of the mind that I’d give New York City three months to make an impression, say “yes” to absolutely everything (you can confirm this with Sarah, if you like), and then move on to my next adventure. I’m almost six feet tall, Sarah is a little over 5-foot, but I borrowed her clothes and made the most out of some extremely high hemlines. Time being as scarce as spending money, I wanted to make a lasting impression every place I went, whether it was work, parties, dates, the theatre—whatever. There was a lot to say “yes” to, and I went for it.
All these years later, I’m hiring interns and training juniors. Dressing for work has changed, but here’s the thing — impressions have not. This is true with job interviews and, most importantly, how you present yourself day-to-day. Casual dressing isn’t code for not caring what you look like. If you have enough style to pull off next-level casual style—do that. It’s not about the pieces themselves, as much as how you put them together.
Charlotte Smith is the North American Managing Director for the global executive search firm The Talent Business, and has some strong advice about dressing for an interview, especially when it comes to dressing according to company culture: “If you know 95% of the company wear jeans to work every day then by all means wear them. You don’t want to be the one person in reception in a pantsuit as it will immediately signal that you don’t understand the culture and therefore wouldn’t be a fit. However, not all jeans are equal. In the same way you’d pick your best suit for an interview in the days when that was protocol, think carefully about what jeans you wear. Avoid anything that looks like you just rolled out of bed, is in need of a wash or shows too much skin. You want to aim to look as smart or slightly smarter than the person interviewing you. That way you show that you are taking things seriously and are being respectful of their time by showing you’ve put effort into how you look.”
Remember that old adage “dress for the job you want, not the job you have”? “Dress as you would for at least the next role or two roles up,” Charlotte advises. “Boss-like behavior breeds bosses fast. How you look is an integral part of that.”
Here are 7 easy foundation pieces that will help you stand out in a world of jeans and sneakers.
A WRAP DRESS
DVF Wrap Dress
Short-Sleeve Ruffle Wrap Dress
Who What Wear Wrap Dress
Stella McCartney Deep-V Long-Sleeve Fit-and-Flare Stretch-Cady Dress (pictured)
You might not be able to afford DVF yet—though, if you did, it would last you forever—but a great wrap dress will take you absolutely anywhere. If you only had to bring one item, this would be it. You can dress them up, dress them down, and they look great on every body type in pretty much any setting. I’d recommend short sleeves, so you can pair them with a light layer and still keep your favorite pieces for the warmer months.
Stuart Weitzman Rapture Suede Booties (pictured)
Gucci GG Ankle Boots
Patent Leather Ankle Boots
Something mod, something modern: These booties will be a complete game changer. Pair them with everything from pants to short skirts to super-long dresses. I’d opt for a block heel in case you’re running late to the opera.
A RIBBED TOP
For Love & Lemons Brandi V Neck Crop Tee
Calvin Klein Bell-Sleeve Cotton-Jersey Top
Prada Ribbed Wool And Silk T-Shirt (pictured)
Get this in white, and it’ll be the best investment of your life. You can wear it with just about anything, including simple or statement jewelry. So versatile, it goes with a righteous mini or a giant tulle skirt.
Eddie Bauer Elysian Skinny Cargo Pants
Escada Talass Stretch Cotton Pants
7 For All Mankind Ankle Skinny (pictured)
Jeans didn’t make the list, but twill pants did. They’re much more versatile and you can get them in tons of fun colors. If you buy them in a fun pattern, they are a true instant wardrobe update. And they’re basically jeans. Why no jeans? Because…don’t be like the rest of them, darling.
A PAIR OF BLACK FLATS
Christian Louboutin Air Loubi Red Sole Ballet Flats (pictured)
Valentino ‘Rockstud’ Flat
Serena Studded Slingback Shoes
Pointed or round-toe, platform or ballet-style, a great pair of black flats, now and forever, will be one of the best investments you’ll make.
A TAILORED JACKET
Dries Van Noten Plaid Madras Blazer
Dolce & Gabbana Singe Breasted Blazer (pictured)
BCBGeneration Open-Front Blazer
The word “tailored” isn’t old fashioned, or at least, it shouldn’t be. It refers to something that fits your specific body type really well. From florals to seersucker, buttoned or zipped, long or cropped, denim to leather — I guarantee you will wear this everywhere. And you don’t have to pay a lot. It’s just more fun when you do.
AN LBD (Or Two)
Ted Baker Saloane Dress
Ralph Lauren Satin Trim Dress
LoveShakeFancy Natasha Dress (pictured)
This really needs no explanation. When I moved to NYC I actually brought two great LBDs with me: One had a bandeau ruffled top that could be belted for different looks, the other had a plunging neckline that I could layer over a tank for work. And if you think I didn’t wear the latter to work and then discretely change out of the tank on my way to an evening engagement, you don’t know me at all. Plunging necklines are in order when you decide to say “yes” to everything.