12 Questions to Discover Your Personal Style

What's your personal style?

Are you ever a little ashamed when you feel like you don't really have one?

Wouldn't shopping and getting dressed be so much easier if you did?!

Let's make that happen.

Press play right now on a scavenger hunt to discovering your personal style.


Oh, and I promise these 12 Qs are ones you've never been asked by any fashion magazine!

This, is the educated woman's guide to style, m'dear.

Pour yourself a cup or a glass and watch now.

There's also a way for you to share with me after, so I can't wait to hear what you discover ...

To Leaping With A Net

A year ago I would have been too nervous to wear this outfit on the blog.

I was afraid you might look at it and think, "She looks great but if I wore that to work people would give me looks all day ... She can pull that off in fancy New York City but that's never going to fly in my daily mom life ..."

It seems laughable now, because let's be honest -- it's a top, skirt, necklace, shoes and sunglasses. It's not rocket science.

Yet, I was holding myself back. I told myself that I needed to dress relatable, in a way that didn't push the envelope. While most style bloggers are thrilled to push the envelope, Dean Street Society is not about being fashion forward, it's about making style attainable for you, giving you an educated style that makes you feel beautiful and empowered more easily than you ever realized was possible.

And I had an aha moment that if I was playing small in my life, how could I ask you to play bigger in yours?

So I decided to wear what I want to wear. Which is exactly what I want for you.


What are you afraid of?

To be too big, too bold, too fancy, too sexy, too much?

To look like you're trying too hard, like you want attention?

You may not believe me now, but I promise no one else would think that.

They'll notice. Absolutely. Dressing better, brighter, bolder brings compliments! Which can feel uncomfortable when we're not used to them.

But betty, there is a joy that comes when we as women are complimented on our beauty ... I can't put into words what a deep, soul-filling place that is when you're owning your loveliness.


Shop this Style { Black & White Blouse : Asos | Black & White Midi Skirt : Asos : Similar |  Statement Necklace : J.Crew : Similar | Blue Suede Heels : Jessica Simpson : Similar |  Sunglasses : Target  : Similar } + Brooklyn Photography by Bethany Michaela 


What would happen if you started taking risks?

Think about your answer over the next couple of days, but I have great news for you. You don't  have to leap alone. Or without a net.

Style & Styleability is coming back this week. It's a community of women committed to shining brighter -- to being more joyful professionals, confident mothers, glowing wives, beautiful friends.

Pop in your email so you don't miss my FREE video series as we go deeper into this heart-to-heart conversation. {Sneak peek: The final video we dive into this specific conversation around fear.}

The winds are changing here in Brooklyn as we enter into fall, a new season, and I can feel it in my bones that there's a new season right around the corner. 


P.S. I have another confession to make. 

I shot these photos six months ago. {The  summer got busy and not everything made it onto the blog right away.}

At the time, they did feel like pushing the envelope. Now, they feel so comfortable it felt silly to write that they had ever felt risky.

You have no idea how much you can grow in your confidence in the next six months.

There's no reason to wait. Take the little leap of watching this series. Set aside time to honor yourself and your growth, and see what happens ...

Stuck in a style rut? Press play.

She's back!

It's the grand re-opening of my beloved video masterclass for just the second time ever.

Live for a limited time only, so hustle your bustle and watch it now

Do you have a friend who deserves to look as fabulous and professional as she is?

Introduce her to the free series at StyleandStyleability.com.

Sharing the inside scoop is always on trend in my book. {wink}

Movie Moments in Everyday Style

Movies make you wish.

Wish you were Audrey Hepburn dancing with Fred Astaire or life had moments Nicole Kidman swinging high above the Moulin Rouge.

Wish you had Kerry Mulligan's wardrobe in An Educated Style or Gwyneth Paltrow's in The Talented Mister Ripley.

It can feel exhilarating, lovely, and far away.


Life doesn't just have to be pretend.

With the right teaching, tools, tweaks, tricks, we can take those glorious mavens of the movies and let them truly inspire us today in our real world.

I was having one of those "if only life were ...." moments earlier this summer when watching The Talented Mister Ripley and decided the next to declare that, "life is now".

I stood scanning my closet, mentally breaking apart what it was I loved about Gwyneth's style, and voila.

A brand new outfit I'd never paired together that made me feel just as romantic, effortlessly chic and timelessly feminine.

Shop this Style { White Button Down : Trina Turk : Similar | Blue Midi Skirt : Vintage, Broadway production of 42nd Street : Similar |  Retro Swimsuit Top : c/o Albion Fit | Brown Wedges : DSW : Similar | Lipstick : MAC in Lustering } + Photography by Michelle Kim 


Even better, this outfit features a skirt I inherited worn by leading lady, Peggy Sawyer, in the 1980's Broadway production of 42nd Street.

I've performed that musical over 500 times including with the Broadway touring company.

It would be easy to take a costume piece and say it feels too much, too dated but I was determined to reclaim it and give it a new life. 

Now is the time to stop wishing, and start making things happen.

I'm bringing back my special class, Style & Styleability, this fall and the grand re-opening begins on Thursday!

It's all about making the ideal, real.

Stop simply being inspired from afar by style blogs, Instagram, movies and magazines; start learning the secrets yourself to create the style and lifestyle you desire.

More on Thursday, but till then, I highly recommend you pop something lovely on the television tonight and let it not just make you wistful, but wide-eyed with new ideas.

P.S. She's here on Thursday. Get on the list now to be the first to watch!

The Little White Dress

I hate rules.

No white after Labor Day? Has that person never seen white jeans with a cozy fall sweater, a winter bride or a stunning white peacoat in the snow?!

Not to mention, let's be honest, September is when I am the most tan and thus, looking the most like the hotness in a white dress, so you best believe I am rocking every one in my closet right now. {wink}

And finally: sales. Lady, this is totally the time to stock up on darling sundresses and swimsuits {did you read my post on the science of style behind swimsuits?} at a steal of a deal to have them on hand for the winter beach vacation you're already planning {I'm not the only one dreaming of ditching the snow for the shore come January, right?}   


A white dress is classic, charming and chic.

Aside from not being able to wear her to a wedding, she's a go-to I believe looks beautiful on every woman if you find the right silhouette for you.

And yes, she works for all seasons. This floral is probably too summery to pull off, but keep your eyes on Instagram and I guarantee you'll see me wearing plenty o' white this fall and beyond.

Plus she lets you play with any accessories or colors like this blue weekender {that I've been living in all summer for last minute trips to the Hamptons or repeat visits on Sundays to the beach}, polka dotted hat, floral bikini ... anything I want to play with, she's game.


Shop this Style { White Dress : Asos  | Weekender Bag : c/o Lo & Sons |  Retro Swimsuit Top : c/o Albion Fit | High Waisted Swimsuit Bottoms : c/o Albion Fit |  Straw Fedora : Accessorize : Similar | Sandals : DSW : Similar | Necklace : Similar } + Photography by Michelle Kim 

Here's to breaking rules, love. 

And instead embracing principles. That's what I teach inside Style & Styleability, which happens to be coming back right around the corner ... {Get on the list today!}


P.S. To celebrate my 3 year anniversary for Dean Street Society, I want to hear from you!

Take 3 minutes to complete our first ever survey here.

Plus be entered to win a gaggle of stylish gifts from shops like Shamelessly Sparkly, Moorea Seal and Angela Kay Designs

Reply by Monday September 15th to be entered!