Listen To Your Desires



I kept noticing floral pants. Which when trying to create a works-with-anything wardrobe while traveling, were totally impractical. [Aside: This was on my four month sabbatical during which I packed almost no clothing to shop along the way.]

Yet after a few weeks of shopping I found myself gingerly fingering yet another pair on the hanger and said “Listen to your desires”.

I was repeatedly drawn to this item for a reason — likely the floral prints that feel like spring/summer, the bright colors amidst a neutrals travel wardrobe I was starting to tire of, the fun kicky-ness of patterned pants that exude the confidence of an American girl on holiday. So I tried them on and they fit like a glove.


At first glance they weren’t the most versatile choice I could have made on the road.

But as I mentally rifled through the tops in my suitcase, I realized they went with everything — white tank, beige sweater, denim shirt, black sweater. Though the pants weren’t versatile, all my neutral tops were. Ditto to my shoes — nude sandals, tan boat shoes, beige heels — and I could see these pants being worn day or night.

What I thought at first was impractical, actually expanded my wardrobe. The pants were one of the more fashion forward pieces in my suitcase and thus I could pull them out for an elevated tourist look while still wearing comfortable loafers, or an easy polished drink even though I had pinned back pool hair and no makeup on for an evening.


The thing about a more bold item, is it makes everything else easier — hair, makeup, accessories — with these pants I didn’t have to try hard at all and yet never felt schleppy.

Most importantly, they make me happy. They’re fun, confident, chic. Above all I believe in dressing joyfully.

Don’t give into every whim — blowing through your budget or ending up with a closet full of things you never wear. Don’t buy clothes for fancy Saturday nights when 90% of your life is lived on cozy Tuesday afternoons.

However, when something keeps catching your eye in magazines, shop windows, Instagram posts, on other women — listen to your desires.

Maybe you never thought you’d be a woman in floral pants, but after the fifth time finding your fingers reaching for them on the rack, just take ‘em in the dressing room for a spin.

I took these ones on a spin around Europe and I’m so glad I did.


[ top: & other stories // pants + shoes: boutique, italy // hat: street vendor, paris // necklace: boutique, brooklyn // photographer: erin + gabri // location: santa margherita, italy ]

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P.S. Want more freedom and clarity in what you wear?

Don’t miss my video masterclass 3 Steps to Simplified Style live for a limited time!

More joy and less overwhelm in shopping and getting dressed?

P.P.S. Once I got home I remembered these weren’t my first of floral pants, as I went double floral in this shoot in Brooklyn. And here's the above pants in action in Portofino, Monaco, and Paris.

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Travel In Style

Location: Amsterdam, NETHERLANDS


Mom taught me to dress nicely for airplanes. She recalled the days when it was a treat to fly, like going to a nice restaurant.

These days airport style is apparently a thing with endless articles of celebs on travel day. Though they rarely look to me like they’ve thought about sinking into tight spaces for long stretches.

So whether you’re with Mom or the gossip columnists, here’s my secrets for traveling in style, both chic and comfortable, without forsaking either:


#1: Black and white. The Chanel color palette is always chic, and you can get away with that make-up-free messy-bun when you rolled out at 4am. It’s the travel base of my 2-Part Fashion Cocktail [more on that in an upcoming class]: the better you dress, the less you have to primp.

#2: Chic cozy pants. These are one of my favorite categories in my closet, period. The key is finding soft fabrics, a little roomy, with some structure to them so they look a bit more like slacks than sweats. Test them out in the dressing room by sitting, crossing your legs, make sure they’re comfy to take a plane nap.

#3: The classy layer. Pack the zip-up or sweatshirt and chose a soft piece with structure or draping as an on/off option for the hot/cold plane moments and different climates when you land. A relaxed boyfriend blazer, cropped cardigan, chunky sweater are clutch.


#4: The profesh carry-on. My carry-on is my everyday laptop bag [actually a diaper bag, shh]. What’s important is that it looks nice, is functional with space for my computer, books and various pockets, and most importantly it’s comfortable dispersing the weight with it’s backpack straps as you walk and stand about all day and around town when you arrive.

#5: The sweet spot shoe. They are not tennis shoes, nor are they heels. You’ve got to take them on and off quickly for security. If you don’t like being barefoot at the airport, you’d like them to be worn with socks. So with all that, some version of loafers or low boots are my go-to.

Then put on sunglasses to cover your tired eyes on the way to the airport, makeup on in the car or when through security, and headphones on to get some joy with music, podcasts or audiobooks to make this an elegantly excellent travel day wherever you’re headed. [wink]


[ blouse + pants: nordstrom // cardigan: forever 21 // boots: dsw // backpack: lily jade // photographer: xenia udalove // location: amsterdam, netherlands ]

Final note: Look at all that goes into a travel day ensemble!

Not to overwhelm you, but to acknowledge why style can feel overwhelming. There’s a lot to consider! It’s not rocket science, but there are reasons and elements to why you don’t feel chic or comfortable or [fill in the blank].

Once you crack the code to understand the principles, they become muscle memory and creating outfits you love and feel great in, becomes a snap.

As detailed as this simple look might sound, I basically wore this same outfit for every travel day during my four month sabbatica [ahem, lunging selfies]. Once I know what works, I just wear it and go.

Want more ease not just on travel day but everyday? Watch my 3 Steps to Simplified Style masterclass here for free for a limited time.

The foundations of fashion may be complex, but an educated style makes your life feel so much more effortless.

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Paris and the Smallest Ballerina

Location: Paris, France


The tank top didn’t look right under my leotard. None of them, all three I tried in vain. They were bunchy. The other girls’ had looked … different. But why?

Eleven years old I stared at myself in the mirror trying to decode how to look like the older girls in my ballet class.

Swap ballet with school or church and didn't you try too?

Explaining to my mom wasn’t helpful. She apparently didn’t know anything about cool girl ballet style.

So I decided to be brave; ask Kristen, one of the bubbly, busty, high school girls in my advanced ballet class where I was the youngest and tiniest.

“Where'd you get your tank top?”

“It’s not a tank top, it’s a sports bra.”

Oh … I had the wrong name, the wrong idea, the wrong everything. And very clearly zero need for a bra, sporty or any other kind. Blushing to match my pink tights I hurried off to class to learn to be graceful, ladylike, to move with a feminine maturity beyond my years ... to be beautiful. 


It starts so youngthe questions, the seekingwhat does it mean to be lovely, to look like the women we desire to emulate?

How does one do it? What are the secrets?

And come age 27, 35, 41 and beyond it persists.

Why does that look different on her? How come that doesn't work the same on me?

And neither mom nor magazines nor well-meaning salesgirls in the Anthropologie dressing room hold the answer.

We don’t outgrow our desire to feel lovely. It is not a secret bequeathed with age. It can feel like a whisper you’ve almost caught the tail of your whole life. 

But it doesn’t have to.

You have someone to ask. Hello, nice to meet you, I’m Hilary, former kind of average but not tragic but not particularly cool girl turned stylist.

I’ve spent six years on my own journey, helping hundreds of clients and students, listening to the desires and challenges of women’s hearts and bodies.

And this month, with the fresh hope of a new year, I want to share everything I know with you.

For today, let’s begin with the simple truth that your beauty matters.


It is not superficial, silly or superfluous. It is not about trends, being cool or fashion.

Style is how you honor your heart’s innate desire to feel captivating, to be beautiful, whatever that means or feels like to you.

Your personality, lifestyle, Tuesday afternoons, Saturday mornings, creativity, joy and body just as it is today.

Tune in for the conversation this month starting with a free video series coming soon and I promise to bring more joy and less overwhelm to your mornings.

For every girl who’s stood in ballet class wondering where the cool girls got their tank tops, take my hand and let’s be ladies in silk coats walking the streets of Paris.

Because if I can, you can, and our hearts deserve nothing less.


[ dress + jacket: american vintage // necklace: boutique, brooklyn // shoes: boutique, milan // belt: vintage, london // watch: kate spade // photography: federico guendel // location: paris, france ]

P.S. Quick secret of how to wear a giant shapeless coat: Show some skin and belt it.

The tie in the back gives a bit of a waist, as does the belt of the dress, so you aren't swallowed, get some feminine curves. And the bare ankles and wrists [as opposed to chunky boots and sweater] show it's the coat, not my frame, that's larger. 

Twirling and swishing while you walk, optional, but highly recommended. 

P.P.S. Whose style did you try to decode growing up? Have a reaction to this post you want to share? Please join the conversation on Instagram below this post!

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The Two Halves of Style

Here's the question no fashion magazine ever asks you:

How do you want your clothing to make you feel when you walk into {insert simple everyday or smashingly exciting activity}?

And here's the truth no fashion magazine ever admits:

No "7 Must Have Pieces for Fall" list is ever going to answer that question for you.

You can tear every checklist out of every magazine.

You can know whether you're a winter or summer color palette, an apple or a boy shape, how to take a look from day to night by swapping out your shoes and purse ...

Yet following every rule in the fashion book doesn't mean you'll have a style that feels uniquely and effortlessly you.

When I've dived deep into this question for myself here's my answer:

I want to feel graceful, empowered, wise, delighted and deepening.

That, is how I feel in the ensemble below.


However, it's not just the heart, it is also the head. 

Feeling stylish is about being empowered by the knowledge of what works and why -- an educated style, which is exactly what my mission is here on Dean Street.

Here's 3 more tricks up my stylist sleeve that are happening in this outfit:

1. Black and white is timeless. This vintage dress would look very kitschy if the print were in red and white, or yellow and white, but the colors of this fabric keep a 1950's dress from feeling dated.

2. Pair vintage plus modern. To make sure I don't look like I just walked off the I Love Lucy set, I made sure my shoes, cardigan and hat were all contemporary. Too many vintage pieces look cheeky {unless that's your desired style, then go for it!}.

3. Keep your seasons fluid. This light cotton dress would feel utterly summer, if not paired with a thick cardigan, wool hat and other neutral tones {aka feels more fall than a bright summery hue perhaps}.

There are tons of secrets and tweaks that stylish women know that empower them to wear what they want to wear, when they want to wear it, and pull it off.

That's what I teach inside Style & Styleability, and around Dean Street Society.

So if you're looking for the educated woman's guide to style {and since our Dean Street bettys are a whip smart savvy bunch, I know you are} you've come to the right place. 


Shop this Style { Black & White Dress : Vintage | Black Felt Hat : Flea Market : Similar |  Black & White Jacket : Forever 21 : Similar | Polka Dot Heels : Next UK |  Rings :  Moorea Seal + H&M } + California Photography by Michelle Kim 


There's a crisp new air in the season with fall, love, and I think you're on the cusp of taking your style to a whole new level.

Can't wait to help you get there ...

P.S. Want more style secrets plus a look at a day in my life?

I am so flattered to be one of the cover stories for Cupcake Magazine's fall issue featuring one of my entrepreneurial idols, Bethenny Frankel, who was photographed by my dear friend and Dean St photographer, Sara Kerens!

Read the story here.

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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 ...

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