Career Chic Council: Meet Anne Caprera


Talk about a power player. Anne Caprera is the political director for the Democratic Senatorial Campaign Committee. She works on Democratic campaigns for Senate across the U.S., advising candidates on everything from budget and staff to TV advertising. 

Thankfully, being a Washington powerhouse no longer requires ill-fitting suits. As Anne puts it, “We have been liberated from the scourge of shoulder pads.” Here’s how she dresses for confidence in the capital.

What’s your daytime work style?
Campaigns as a general rule tend to be very casual workplaces. The Senate is not. My work encompasses both, so I try to strike a balance. I never know whom I will meet with on a given day, so I try to make sure I am always looking professional.  

I try to follow the advice I give the female candidates I work with and for: It’s okay to be original and daring in your work wardrobe, as long as you are paying attention to the cuts and fabrics that look good on your figure. Some days I’ll wear a plain black dress with a big, bold necklace. On other days I like to bring a lot of color into my wardrobe.

And I’ve been known to plan an entire outfit around a (great) pair of shoes. You can’t go wrong with a Ferragamo Varina Bow flat. And I admit I’ve got a pair of L.K. Bennett Sledge nude platforms, a la HRH Kate Middleton.

How do you take your look from office to evening?
I love that so many designers are showcasing sheath dresses for work attire. A great sheath dress looks professional and sleek and is easily paired with a cardigan or a blazer for the workday. All you have to do is take off the cardigan or blazer for an evening event or happy hour.

The trick is all in the cut of a dress. If you are wearing something appropriately tailored to your body, a change of shoes or earrings (or both) is all you need to go from the office to evening. I absolutely love vintage jewelry, whether it’s my grandmother’s or a silver Moroccan dowry bracelet I found in Israel.

Of course, I once went on a date with a guy who told me that the long (and modestly figure hugging) Anthropologie dress I was wearing didn’t show off my legs enough. I told him that his suit didn’t show off his pecs enough and left him at the bar.

What’s your weekend style?
The funny thing is that I have an easier time dressing for work than I do for anything casual. My weekends are pretty active: I am at yoga on Saturdays and usually go for a run on Sundays, so I am always in workout clothes.

When I’m not running around in yoga pants and tank tops, I can be found in a pair of jeans and a tunic. I like Hudson and Paige jeans—they have just the right amount of stretch. When I’m not at work I like to be comfortable.

What’s your best piece of personal style advice?
When I was in college, I went out of my way to look like I didn’t care about fashion because I thought that made me more “serious.” I bummed around in mesh shorts and T-shirts and generally looked like I didn’t care what I put on my body. A friend nominated me to run for president of our student government, and I’ll never forget this line from his speech: “Even though Anne doesn’t get dressed up, she’d make a great president.”

It was the first time I realized that how I looked and presented myself made a great deal of difference in how seriously people took me—just not in the way I thought.

Here’s what I have learned in the years since. You should love the things you wear and you should feel great wearing them. The right style doesn’t diminish you; it gives you confidence. 

I spend my days helping senators and future senators run multimillion-dollar campaigns. The fact that I can discuss the merits of peplum dresses versus pencil skirts does not make me any less able to talk about what will happen in Congress over the next month.

You can be smart, strong, and stylish all at once. Don’t let anyone tell you otherwise.

Anne Caprera has got it together, and there is a lot we can take from her style. Anne often finds herself moving between two worlds, one more casual than the other.  Shift dresses and good shoes are two of her essentials, and she often builds her outfit around those elements.

Anne touched on her love of vintage jewelry; some of her favorite pieces came from her grandmother while others she’s collected in her travels. But you don’t have to rely on a grandmother with good taste or an opportune trip to start your own collection. One of my favorite sources for vintage pieces is eBay. Here’s where to go for vintage costume jewelry and vintage fine jewelry.  

eBay can be overwhelming — so here are a few tips to get you started. Since searching for costume jewelry can be a little less intimidating than looking at the more expensive stuff, let’s focus on that. (And if you find it all a bit too much, we have a great vintage-inspired piece below, too.)

How to Search for Vintage Costume Jewelry on eBay

1. Keep track of designers you like.
Some vintage costume jewelry designers you might try include Trifari, Kenneth Jay Lane (sometimes abbreviated KJL), Hattie Carnegie, Miriam Haskell, Jomaz, Hobe, Juliana, Schiaparelli, Lanvin, Monet, Joseff, Napier and Ciner. (But keep in mind that there are tons of amazing unsigned pieces, too!)

2. Keep track of helpful search terms.
Searching for a vintage statement necklace? Of course, you can search for the obvious (“vintage statement necklace”) but there are other search words you can try. “Huge,” “massive” and “runway” are three that can bring luck. Jot them down to make your next search easier.

What kind of necklace are you looking for? Maybe you are looking for a bib, collar or pendant — be sure to use the specific term. And how about a bracelet?  Try narrowing your search with a term like “bangle,” “cuff,” “link” or “clamper.”

4. Search by period or movement.
Some to try: “Modernist,” “Egyptian Revival” and “Art Deco.”

5. Search by material, color or other design detail.
Some terms to search: Glass, Bakelite, Lucite, celluloid, beaded, enamel, rhinestone, gripoix, gold, silver, pearl, filigree, carved.

See our stylist's picks on the next page.

Anne Capera


1. The Black Sheath Dress
You can’t go wrong with this piece. It’s figure flattering and timeless. This length is work appropriate in almost every environment.
Magaschoni ponte knit sheath dress, $348, available at

2. The Cardigan
A cardigan is a wonderful layering piece, and it definitely doesn’t have to be basic or boring. This one has clean lines and a sophisticated flair.
Long sleeve cardigan, $129, available at

3. The Colorful Blazer
A vibrant blazer is a great way to change the look of a simple dress. I love the way this collarless design keeps things modern with an eye-catching color-block of bold purple and black.
DKNY jacket, $445, available at

4. The Colorful Sheath Dress
Anne mentions (more than once!) her love of a well-cut sheath dress, and it’s easy to see why. Its versatility and wearability are perfect for a woman on the run. This blue sheath is a must-have when you want to switch things up. And don’t forget that you can change the belt! It can transform the entire look of the dress.
Jewel-neck sheath, $129, available at

5. The Black Flat
Anne mentioned her love of the Ferragamo Varina bow flat — and for good reason: It’s a fantastic work shoe. 
Ferragamo Varina patent ballerina flat, $450, available at

6. The Taupe Pump
Anne name checks L.K. Bennett’s Sledge taupe court shoe (or pump, as we are prone to call it Stateside). It’s one of Kate Middleton’s favorites—just Google “Kate Middleton L.K. Bennett Sledge” to see how versatile it is! 
L.K. Bennett Sledge pump, $345, available at

7. Vintage-Inspired Statement Necklace
Egyptian-inspired pieces enjoyed a surge in popularity during the 1920s with the discovery of King Tut’s tomb. Both Egyptian and Deco influences come through in this fab necklace by Lele Sadoughi.  
Lotus bib necklace, $485, available at

8. The Day-to-Night Jacket
Anne mentions how easy it is to pair a cardigan or jacket with a sheath dress for work and simply take off the top layer before heading out for the evening. She’s right — but the reverse works as well. Wear a simple outfit to work, using black as your base (a black dress or black pants). Come evening, dress it up with a modern but glamorous jacket like this one.
Sequined jacket, $198, available at


Meet DawnDawn Cassidy is a fashion writer, personal stylist, and previously author of the blog Enterloop. She currently is expanding her Personal Styling services and plays host to intimate events in the NYC market. She is a graduate of Fashion Institute of Technology.

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