Jobs For The Girls: The Personal Stylist

Given that I’m the sort of person who’s brain switches off the minute anyone starts talking about “clashing prints”, and that my need to start mocking whenever anyone talks about  the latest trend is so innate it must be in my DNA, I was very, very excited to start putting together a post on the “behind the scenes” of a personal stylist.  We’ve had Jobs for The Girls on a whole range of fascinating careers, from a scientist, to an interior designer, to a PhD candidate.  We’re nothing if not diverse.  So yes, let’s throw a personal stylist into the mix.

Step in Hilary Rushford, founder of Dean Street Society, a personal stylist service.  Gone are the days of a personal stylist being a terrifying matron in the changing rooms at Debenhams thrusting monstrosities into your hands and demanding that you zip them up and parade in front of your mirror.  Hilary’s philosophy is about helping her clients discover the best version of themselves and helping them dress to make the most of that.

And honestly, readers?  I was blown away.  By Hilary’s drive, and enthusiasm for what she does.  I was made speechless by how hard she works, by how honestly she answered these questions, and how much she loves her job.  I bloody love Jobs For The Girls.  And this is why.

Hilary Rushford, founder, Dean Street Society.  (ed – I want those shoes)

Clearly, if Hilary’s not lurking menacingly around the changing rooms of department stores, what does a personal stylist do all day?  Over to Hilary: “I launched Dean Street Society 13 months ago and I’d say the rhythm of my work has changed almost every month. It goes in waves as to whether what’s keeping me most busy from a client perspective are one-on-one clients, or photo shoots, or on-camera hosting. 

However, most of my time is spent “in the office” which means either working from home or nearby coffee shops, with my assistant a few days a week. Some weeks I have so many clients and appointments, meetings that I won’t have an “in the office” day & that starts to make me feel really ungrounded & frantic. Other weeks I miraculously have 3 or 4 days “in the office” and my focus can just really be on building the business.

While that makes me feel more grounded, it’s also more overwhelming because my to-do list is always so long & there’s no rhyme or reason to whether I should prioritize my email inbox, writing blog posts, writing guest posts, social media, community sites, filming videos, taking photos, Photoshop, creating products, doing research. I suppose in short I could say that the vast majority of my time is spent alone, in front of the computer. Which might sound miserable to some people. But I’m so passionate about what I do, that I actually adore just getting to zone in & make things happen! Though of course being in client sessions & on shoots is so fun & rewarding.”

Hosting a style show for Hearst Media this Spring

And that’s the bit I’m interested in, the passion.  What are the bits that Hilary loves the most about what she does?  “Two things really light me up: When someone “gets it” and when I feel like I’m operating at my highest potential. That moment when a client looks in the mirror and can’t believe how great they look, or says “I think I’m really starting to understand this!” — I love those moments. I love teaching. Knowledge is power and my clients feel so empowered when we’re finished that I swear they have a glow to them. It makes me cry to think about.”

And of course, the bad. What’s the hardest part?  “Any and all things to do with technology! I’m not tech inept. But when you’re outside of your skill set, it takes you ten times longer to do what someone else could do in a snap. That’s absolutely the most challenging and maddening part of running your own business. When you haven’t yet reached the tipping point when you can hire someone on, you know you’re leaking precious time you can never get back.”

My Instagram Challenge lets me give readers a free month of style inspiration

So if someone wanted to become a personal stylist, what would they have to do?  What qualifications would they need?  It might help to hear that Hilary didn’t have a typical background for this.  Also her views on training and qualifications are unique.  “Training is such a personal question. I went to school for musical theatre, but I got cast in a Broadway company truly because of the tap teacher I had from ages 4-14. It wasn’t my four year degree that booked me that job. I have friends who moved here at 18 and were on Broadway that year, and others who went to a top school and the respect and connections that came from that were what opened amazing doors for them.

For me, styling is something my friends told me I should do. It’s something I was already doing simply because people were asking. I didn’t realize I was that uniquely gifted at it because sometimes you need other people to point out, “Hey, this thing that comes naturally to you, doesn’t come naturally to everyone.”

The training I’ve focused on is not in fashion knowledge or specific stylist skills, but in being an entrepreneur and running your own business, as well as the psychology and culture studies that help me understand my clients and the market. Those things, have been invaluable for me. At the core, I’m a business woman and a counsellor, who happens to deal in fashion.

Ultimately the tools I think you need are 1. A strong knowledge of business & entrepreneurship 2. An excellent grasp on psychology & interpersonal communication 3. An innate aesthetic eye & understanding of fashion.

You’ll notice that only 1 of those 3 actually has to do with fashion.  In general I think it depends on everyone’s background & what the areas in which you need to seek out more training & education”

I try to make my style posts education, not solely inspiration

And, other than the above, what are the characteristics of someone who is a successful personal stylist?  What do you have, and what do you wish you did better?

“First & foremost you need to be a rockstar business woman. You have to understand how to run a business: marketing, public relations, customer service, sales. Unless you’re going to start as a stylist under someone who already has a company, most of the stylists I know are running their own business and I think it’s a very specific type of person who really thrives and survives as an entrepreneur, because truly being your own boss is an insane, though awesome, undertaking.

Secondly, you have to understand and know how to communicate with people. If you’re a buyer or in charge of merchandising, then first and foremost you can focus on the clothes. But as a stylist you’re dealing with people’s most deeply personal and nuanced issues of body image, finances, life stage, success, relationships. People share things with me they would only share with their best friends & their therapist. A client in a killer outfit, who hasn’t been heard and affirmed, is not going to be a success.

And finally, you have to be a teacher who can really explain the mathematics of why an outfit works, why a trend is popular, why a style is flattering, why a piece isn’t worth the financial investment. If you’re an editorial stylist only doing photo shoots, then you don’t have you don’t have to explain yourself to the art director necessarily. But as a personal stylist you have to be able to teach while you style so that client can go on to replicate that level of success once you’re gone.”

My job is about people becoming the best versions of themselves.

Working for yourself must be exhausting.  How do you stay motivated? Is it hard to keep pushing yourself to keep developing?  ”I’m hungry. I just think it’s in my nature. I have never not been driven and passionate. I fundamentally don’t understand people who aren’t. It’s like someone saying they don’t like chocolate. “How can you not like chocolate?!” I cry!

On an overarching level, I have this compelling vision for the brand I’m building that absolutely drives me every day. However, in the day to day … the motivation is definitely more challenging. It’s not a lack of desire to develop, it’s a constant battling of the overwhelm. It’s knowing what to focus on that day, making it happen, 8 hours later feeling like you’ve barely made a dent, and yet doing it all again tomorrow. But I suppose what really keeps me motivated at this point is half paying my rent and half that vision in my head of knowing I’ll make a difference when I can get my message & knowledge out to more & more people. Perhaps it’s that micro & macro balance that’s the key for me.”

Working form a beach in Puerto Rico this Spring was my definition of “empowered”

And in every job, there’s the balance of compromise and reward.  What is it here?

“In just my second year of business the compromise is definitely spending time on things that aren’t my strengths — the website, the technology, the Photoshop. I can’t afford to have a full team right now, so it falls to me to do almost everything. The compromise of that is not the “I don’t want to do this because it’s not fun” — some of those things I actually enjoy, I’m just not fast at them. Instead the compromise is “There’s knowledge in my head that’s not getting out and helping people, because I’m creating an html page today instead of an e-Book.” That really is so hard to swallow.

The biggest rewards are feeling empowered everyday to do something worthwhile, and the feedback I get from clients and readers. As an actor, no matter how hard you work, someone else has to open the door of opportunity and cast you. As an entrepreneur I feel much more in control of my ability to move my career forward everyday. And the fact that in doing that I hear from people that I’ve changed their lives — it leaves me speechless. I’m so humbled and overwhelmed by that, and so grateful that’s my job.”

And the tough question.  Does your work push you outside of your comfort zone? If so, when?

“All the time! I’m nervous at every client session. Every one. Because there’s no formula. Everyone’s closet, body, budget, style level is different. There’s no guarantees. I can’t give everyone the same speech, the same tips, pull the same pieces in the same store. But one of my mentors said she gets nervous everytime she gets on stage to speak and that if she didn’t, she’d think she was becoming complacent; that the nerves are your drive saying, “I really want this to be exceptional because I know I’m capable of it”.

Being a solo-preneur also means having to pitch yourself, approach people, network. As an actor I could just see an audition posting and show up. Now I have to ask to be seen, heard, considered. Though most people would probably find auditioning terrifying, I actually find this more nerve-wracking.”

Behind the scenes at an engagement shoot.

The nosy part of me always wants to know everyone’s plan B.  What they would have done if they weren’t doing what they were doing now.  What’s Hilary’s? “ My first career was in musical theatre, which I did professionally for almost a decade. I toured the country, performed with some of the most elite companies — I adored it. I always thought I’d then transition into a master’s degree and teaching at the university level, but two years ago I realized that would mean leaving Brooklyn. I realized my life here meant more to me than that dream, which is when I went on the process of self-exploration {cough, breakdowns splayed on my couch with my best friend wailing about what I was going to do with my life} and realized that I wanted the freedom & empowerment of being an entrepreneur.”

And finally, one of my favourite questions because I believe everyone should have one: do you have a mentor?

“I am actively seeking out more mentors. If you have one, send em my way! For whatever reason, I have a lot of friends who are at or a few steps behind where I am. So I get asked to a lot of coffee dates to give advice, but I am honestly really searching for more relationships where I can go to ask advice of them. I have teachers I would consider mentors, but we don’t have a personal relationship. Their courses and classes have been so valuable to me. But I am definitely daydreaming right now of a mentor I could have a one-hour call with every Monday and get clear on my priorities and my business plan that week. I’m happy to do that for others, but the truth is that I’m still new at this and could really use the mentorship myself! Granted, that will hopefully never change as I think you should always be growing.

Also, I’m my harshest critic. Some people might really need someone else to give them an outside perspective and an occasional kick in the pants that they need to be working harder or implementing more. No one could be harder on me than I am on myself. I’m like a little scientific researcher — always aware of what went better in that client session or photo shoot or filming segment than the last time, what the bumps were, how I could do it better. I think perhaps this goes back to my micro and macro reasons for being motivated. Paying your bills as a an entrepreneur in New York City is no easy task. So no one cares more about my rent check than I do. And my vision for what I’m building Dean Street Society to be is so marvellous it gives me goosebumps just to think about it. So no one is more compelled to make that dream come true than I am. I know how I help people on a small level now, and I feel a responsibility and a delight at knowing I can do that on a medium and on a large level if I stay focused and build this brand to its full potential. I dream about it all the time. But I also realize that I’m living that dream out right now. And I don’t take a day of that for granted.”


Thank you so much, Hilary.  For doing away with my stereotypes and bringing such passion and drive to these pages.

Readers, I know the purpose of JFTG is to give you an insight into the world behind the woman doing the job, but if you fancy meeting Hilary and benefiting from some of her expertise then she’s offering the following offer to AOW readers:

Hilary is bringing Dean Street Society to the UK & will be booking clients in London for TWO WEEKS ONLY {December 2-16}.

She’s got special deals of 15-25% off. Hello stylish new you in 2013 & taking your life to the next level in the new year!

Categories: Jobs For The Girls
15 interesting thoughts on this


  1. Posted November 26, 2012 at 7:30 am | Permalink

    Yay! So good to see Hilary on these peachy pages x

    • Posted November 26, 2012 at 7:38 am | Permalink

      Yay! I agree! Hillary is inspirational- love following her on twitter.

  2. Yanthé
    Posted November 26, 2012 at 10:39 am | Permalink

    Wow. Her drive is so inspiring! If a personal stylist were in my realms of possibility right now I would be after one of those slots pronto!

    • Posted November 27, 2012 at 6:42 pm | Permalink

      Thank you Yanthe! Would love to meet you in person if you’re available to swing by our Holiday Hangout next week! {Details on the blog}

      with grace & gumption, Hilary

  3. Lara Blue
    Posted November 26, 2012 at 11:56 am | Permalink

    So interesting and inspiring :)

  4. Posted November 26, 2012 at 1:19 pm | Permalink

    I love Hilary’s stuff and it is so cool to see her here and read more about her inspiration and motivation. It is inspiring.

    • Posted November 27, 2012 at 6:43 pm | Permalink

      Siobhan, so hope I get to meet you in person when I’m in town!!

      with grace & gumption, Hilary

  5. Roz
    Posted November 28, 2012 at 11:28 pm | Permalink

    Loved reading this! Thought I left a comment earlier in the week but my iPhone must have eaten it! Off to dream dreams of being a personal stylist. Hilary would be lovely to meet you when you are in London, I think Bex (@OliveDragonfly) has been in touch with you about it :D xx

    • Posted January 2, 2013 at 10:37 am | Permalink

      Hi Roz! So sorry I’m just now seeing this & we haven’t gotten to connect. I’m headed home soon but hoping to be back this spring. Would love if you’d drop me a note to so I can hang on to your email address for when I am!

      with grace & gumption, Hilary

  6. Posted November 30, 2012 at 9:46 pm | Permalink

    Hillary, you’re so inspiring and positive! Thanks for this great & honest interview! You’ve given me hope that maybe perhaps I too could do this, since personal styling is something that I’ve always wanted to give a go.

    Keep doing what you do! With all of your grace & gumption! :)

    • Posted January 2, 2013 at 10:38 am | Permalink

      Aww Lauren thanks so much! Would seriously to love answer any other Qs you have about it. I do a “small business” post each Friday & if you leave a Q in the comments there I try to answer them in future posts. :)

      with grace & gumption, Hilary

One Trackback

  • By Jobs for the Girls – Building Surveyor on January 18, 2013 at 12:45 am

    [...] of what she does for a living. When she first offered to feature alongside the Family Lawyer, the Personal Stylist and the Analytical Chemist (to name but a few!) Cheri had the following to say about her job [...]

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Hello! We're Clare, Aisling and Anna and welcome to a corner of the world where smart, flawed, real women talk about the bigger picture; about their experiences, stories and opinions on all aspects of being a woman today, from marriage to feminism to pretty, too.

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