MBA NYU Grad, tech enthusiast, female entrepreneurship obsessed, with a love for fashion and how clothes can transform women into more confident, cool and collected employees in the workforce in any industry.
Catching Elephant is a theme by Andy Taylor

Amy’s story is fascinating to me. A business school friend, Gus, who runs a web site with advice on transferring from military service to business (Check out Service2School) and graduate schools approached me about giving advice to ex-military on what to wear. When we chatted about it, I didn’t quite have full knowledge of what it would be like to make this transition as woman in the military to ‘civilian’ life. Gus introduced me to Amy, who is pictured above riding a helicopter during a mission (how many of us out there can relate to that one!). Amy grew up in Westchester, not far from West Point, and was drawn to the military out of desire to give back to the country that had embraced and provided so much opportunity for her parents. Her father came to graduate school here in the states and clearly recognized the opportunity it would provide for his future family. Amy is on her way to Wharton in the fall and has already gotten a taste of ‘civilian’ life but the transition was quite daunting and a piece of that centered on embracing her femininity and in tandem with what she should wear.
To put it all in context, Amy hadn’t decided what to wear on a daily basis since high school. Upon entering West Point and continuing onward to serve in Iraq and Afghanistan, she hadn’t really had a wardrobe for 9 years. 9 years! And this includes much more than clothing, during that time, she couldn’t wear earrings, her hair had to be a certain way (much like a ballet bun), and little make up if any at all. In Iraq, she said the ‘only time she was not in uniform was when she was in her Pjs’. She also served in Afghanistan for 15 months.
When I took on this assignment I had no idea how much someone in Amy’s situation would be starting from ground zero – sure she had jeans and some weekend clothes but very little and had very little place to start. Yet, she was very self-aware how much it mattered and was excited to ‘embrace’ her femininity – not only was her dress not feminine but West Point is approx. 10-15% female and I’m sure the military in general is not much different. She actually ordered a book on Amazon for 10 bucks on how to dress to guide her. Looking feminine was ‘kinda important’ to her. In this new phase of her life she was ready to ‘express femininity, feel pretty, feel like a woman and express’ herself but it took time and research. When I asked how she would describe her personal style, she said she is still very much figuring it out but it trends towards the conservative side. Even the idea of dressing herself everyday was new. In the business world there are many different kinds of nuances she felt she needed to learn and understand, especially when it comes to having a wardrobe.
Amy first started to build her work wardrobe at J Crew, Banana Republic and Ann Taylor. If she liked something, she would buy it in 3 colors. She used Vogue for a little guidance and just the individual catalogues. Her standard now for PepsiCo which she describes as not particularly conservative (which is all relative to her military experience) is cardigans with collared shirts. And given that the last time she dressed for class was high school, she asked students at Wharton what was the standard, which I think to her surprise was pretty much anything goes. With her sights set on finance, she will certainly be able to use her bent towards the conservative but I bet she starts to branch out just a little because with as much zeal and energy that I heard on the phone and with such a unique background I’m sure some of the colors from her heritage and accessories might find their way into her wardrobe as well.
Below she is dressed up in Calvin Klein, “got to stick to classic brands” on Veteran’s Day with medal of honor recipient at work.
You can sign up for Service2School here.


Caroline is the founder of Pretty In My Pocket, a beauty app and web site to help us ladies keep track of all of our products and share with friends. Still in beta, she’s driven, stylish and southern! I love the mix of style with her chucks! Nice casual chic for a wide range of meetings.
Top: Fabrik
Pants: Theory
Jacket: Thrift Store in Shanghai (keep an eye out for those hidden gems)
Necklace: Tiffany’s
Shoes: Chucks

Jovena has an easy style and both times I complemented here on her outfit, she denied being a ‘fashionista’ but that is probably what I loved most about her! She recently launched her company Skillfer to help the growing demand for developers in New York City. After 2 years of recruiting for Quirky, she started the company in an effort to take a new approach for placing tech talent in start-ups that is truly mutually beneficial, innovative and fill a need that is sorely addressed right now in the New York city tech environment. It’s hard to go one day without hearing about how someone is seeking a developer (or 4!) and I was eager to chat with her about her approach and also how she advises people to dress given the variety across start up companies in terms of what people wear to work.
The first night I met Jovena, she had on a gray blouse, necklace, jeans and flats that fit her well and prompted me to ask about her own style and if she ever advises people on what to wear. Part of the reason I followed up is because I thought about what it must be like to be a female recruiter within the tech world having conversations mostly with guys (which will hopefully change) and how to advise them without coming off as a ‘suit’ herself but still serious and competent. When we met for coffee, it was another easy outfit seen above but still ‘put together’. For someone who said she often doesn’t notice what other people where, she definitely has a sense of what works for her and is cognizant of dressing for, first and foremost, her ‘clients and customers’. This includes coming off as approachable (hence not overtly professional or biz casual dress) and having a two-way conversation as opposed to what can be characterized as a ‘long one-sided interview’.
She has a wide range of clients ranging from more experience tech talent who tend to have a better sense of the start ups they are willing to work for to developers just out of college who need to be educated more closely on the tech community. She is accomplishing this by setting up ‘tech tours’ for young talent to learn more about the culture and environment of a specific start up and interact directly with the employees. When dressing for each of these interactions, as with many situations, it’s always better to be slightly dressed up but to also ‘look like they look’. To do this, she had some great suggestions, that are seemingly simple, but might never occur to a prospective job seeker. The bottom line is to stalk the start up, look up employees on Linkedin, look at the start up blog and find photos to see how people dress (awesome suggestion), and then just take it up a small notch. There are instances where a interview suit will be excused for a moment, an anecdotal story I loved was when she told me about the job posting at Quirky for the CFO. They knew they were looking for someone with finance experience, which traditionally comes with more conservative attire and in fact wrote in the posting ‘throw away your suit’. It helped weed out people from a cultural stand point which she described as the ‘hip, cool, fun-ness of working at a start up’.
I’m excited to hear about more tech tours and how she is able to meet the demands of the growing need for tech talent. I’m sure her easy, comfortable personal style will work for her as she grows her own business and serves the need of the community.
Please check out her web site here.
Follow on Twitter
Or contact: info@skillfer.com

Above pic:
I always admired Julia’s seeming effortless style at school and as I started this project she was definitely one of my target people to interview. Growing up in North Carolina, definitely provided a prim and proper overlay to her creative style and any time we chatted she said she was lucky to have influence from her environment with some of the general mantras of “dress for the job you want” as well as others. She has worked in finance most of her career so her industry of choice combined with southern upbringing has definitely influenced her style to be relatively conservative with a twist. What’s a bit jarring for her style now is living in Santa Monica where anything goes for the most part even if you are a finance employee. I can definitely relate to this transition, no one really wears structured clothes in LA, I remember thinking that blazers over a cute top seemed so stiff and that most girls had slouchy sweaters to cover tops and just an overall more relaxed look.
Julia lives and works on the west side of LA (a lucky commute) and says she is consistently over-dressed in office – even the men are mostly in jeans with a nice button-down as oppose to typical finance dress of the east coast. She doesn’t mind being on the slightly over-dressed side and generally defaults to silk blouses with pencil skirts or dress pants. She feels that women especially should be prepared for anything and anything too tight of too low cut is generally ‘just distracting for everyone involved’. Even though she definitely avoids being sexy, she will wants to have something fun on such as fun jewelry and a pop of color. On the weekend, she chooses either low cut or short just not both at the same time, which still ends up on the conservative side of the coin in the LA world. Overall, she feels if you are “comfortable and feel good about yourself, you’re gonna come off as sexy.” (Love that!)
One mini piece of advice that I loved right off that bat was to belt a shirt instead of tuck it into pants. It provides structure around the waist now that pants are often low-cut and complements a women’s natural body. As I have implemented this into my own wardrobe what I’ve noticed is that the belt doesn’t (and probably shouldn’t) be that tight around the waist and it still provides nice definition. It also looks like I’m more creative to think to add a belt which is a pretty easy fix.
Her favorite brands are DVF, Theory and she is currently obsessed with J Crew, everything from sweaters to dresses to silk tops.
Below:
Vintage necklace


One of the benefits that Elysia told us of working at Calvin Klein is boosting your wardrobe directly from the company. So cute in Calvin Klein dress and shoes!
Industry: Fashion
Company: Calvin Klein
Function: Planner

Meena immediately related to our mission and was proud that she isn’t a label whore but rather chooses clothes that fit and look sharp regardless of who makes them.
Ruth, we learnt was a Harvard grad who lets her hair down at night - literally she wears a bun every day to work as part of her look!

How amazing! When we approached Tamara, we assumed she worked in fashion but she is a Senior Tax Accountant at a Real Estate Firm!
Company: Brixmor Property Group
Function: Tax Accountant
Workplace Wears:
Silk Button-Down Top and Skirt: Banana Republic
Belt: BCBGMaxAzria
Leather Jacket: Elie Tahari
Ballet Flats: French Sole
Tights: Givenchy

Lydia Yao – Start up attire / Former Consultant
Blouse: J. Crew, Natasha top
Cardiagn: J. Crew, Jackie cardigan
Jeans: AllSaints, Pipe Skinny Jeans
Shoes: Marc by Marc Jacobs
Bag: Michael Kors
Watch: Marc by Marc Jacobs
Necklace: Wendy Mink
Ring: Cam & Zooey
Lydia noted that both the shoes and bag were purchased at 50% off from Century 21! The necklace and ring were purchased also at a discount from Gilt. This pic is her ‘power outfit’ in her current role at Seamless.
Companies – Seamless.com / BCG
I met Lydia at a Duke Global Entrepreneurship networking event in NYC and immediately complemented her on her style and typical given the focus of her blog I asked her what she did. As soon as I explained the purpose of this blog, she and I continued to chat about her transition from consulting to start up world and even from college to consulting. Following up with drinks at Boqueria, I learned of her the many challenges that she encountered as she transitioned from each of the phases of her life and how resources were not plentiful to help guide her through each transition.
Lydia started her professional life as a consultant at BCG in Atlanta which she describes “small, suburban and conservative.” It was a great “starter city, and not overwhelming” although with a Mom who was an artist and no tips from Dad or older siblings she was at a loss of what to wear. She wanted to fit in and not stand out but shopping on a budget was difficult so she resorted to outlet shops for suits – Ann Taylor and Theory were the defaults but the key to her looking put together were not the labels it was tailoring. She said “I am a firm believer in tailoring my clothes… if you don’t get it tailored, there’s always going to be something off.” Some early rules that were bestowed upon her and still resonant with her even though she is in a much more relaxed environment now are no open toed shoes (something we’ve written about before here) and no sleeveless shirts (a bit of a new one.)
Through BCG, she was able to transition to New York City from Atlanta, which, definitely allowed for a little creativity but she generally still defaulted to slacks, a shell and a cardigan. When a recruiter reached out to her at Seamless.com, she was excited for a new challenge professionally, but the environment was going to be vastly different from her consulting world. The recruiter even warned her not to wear a suit to the interview! At a loss, she was still somewhat over dressed and on her first day of work was told “you don’t have to dress up” even though the slacks and chunky sweater she had on was already a huge departure from her consulting roots. That being said, she has now found a balance of style with a relaxed twist, she states that when you are given a wide range of options that people can take it in both directions but if you are a bit “more credible when you put in a little effort.” Lydia was wearing skinny jeans, a loose sweater and a long necklace that night and a theme that is becoming more and more present is that when you are dressed up you feel like you’re at work. It’s a change in attitude and shift to confidence.
One of the most interesting points Lydia made was that the focus in the workplace is often what ‘not to wear’ as opposed what ‘you should wear’. Hence, not really have real suggestions out of school on what to wear and having to very much figure it out on her own. Her current start up role has been a challenge and even in the end she was asking me if a sleeveless shirt was ok given some of the ‘rules’ that had been ingrained in her from her first work experience. New York and the start up world allow her a bit more latitude but still within a certain realm she deems ‘business shabby’. Even when she decided on a summer shift dress for her interview she felt overdressed and recognized that there would be a small learning curve to figure out her own workplace wear.

We met Alicia at after work drinks in Midtown - fashionably dressed - I loved her use of color! She describes her personal style below - stay peppy Alicia!
Blazer – Aqua from Blooomingdale’s
Dress – Aqua from Bloomingdales’s
Tights – Joe Fresh
Shoes – Sam Edelman
Company: Gerson Lehrman Group, Inc.
Role: Director | Product Marketing
I try to dress in bright colors and prints depending on the season
because working for a company that is focused on financial services
means that beige, black and grey are everywhere and it gets a little
boring! Plus, since I am in marketing, I do have some creative
license, provided I don’t wear jeans every day. My favorite work
clothes are (obviously) Aqua at Bloomingdale’s because the quality and
price are great. I also like J Crew for pants and sweaters that are
work appropriate in terms of cut, but fun to wear and look at too. My
greatest find of late is Joe Fresh – awesome clothes at a reasonable
price that are like a cross between J Crew and Club Monaco. I also
can’t live without J Crew accessories because on the days when I do
wear gray and black, they help keep me peppy.

It’s amazing how useful a plain white tee can be or a white wife beater tank. I find them extremely difficult to find. Yes, I own a few comfy hanes tees that I bought at a drug store but a nice fitted white tee can be a challenge. If successful, they can appropriately fit under a blazer, sweater, even a suit depending on the cut. For me, Club Monaco has the best fit and I have tried on many in my search for a great white tee for a petite frame on top. I did a quick poll of friends and found that others like James Perse ($50.00), Splendid ($48.00), American Apparel ($22.00), Banana Republic ($22.50) and even Forever 21 came up for $5.80.
New York Magazine also profiled a couple of options here in 2005 but somehow paying $250 bucks is a bit excessive although they did throw Hanes into the mix at the bottom.