What Makes You Feel Beautiful

Location: Brooklyn. New York

It may be that my life mission is to answer, “What makes a woman feel beautiful?” 

At 62 I may laugh at my naivety for thinking I knew my life’s work. Yet for the last few years this has been the whispered question growing louder into a heartbeat with which I see the world.

I believe when a woman feels beautiful she is healed from the brokenness of this world, powerful, peaceful and inspiring.


A friend asked me this question recently and what came to me is I feel most beautiful when I’m comfortable.

In a skirt that isn’t too tight. With friends around whom I can be myself. Knowing my gent thinks I’m lovely sans makeup. Wearing my go to red lipstick. When the house is freshly cleaned and there’s flowers on the coffee table. Comfortable.

I’ve felt divine in an evening dress, or like I needed to suck in all night.

Pathetic for being in sweatpants or delightedly cozy.

Slightly anxious amidst a group of people, or deliciously at peace.

Insecure in a relationship or at home. 

Some times my full makeup is dry and cracking, other times it’s bright and happy.

Some days my bare face magnifies dark circles, others it radiants confidence.

I’ve felt embarrassed and sexy at the exact same weight.


Beautiful isn’t in a certain style, size, season. It’s a choice I can make in my life daily.

Does this make me feel beautiful? This dress, not doing my hair, being around those friends, moving my body. 

If not, what do I need to change?

Perhaps the pants should be given away, the cookie put down, the glass of rose picked up, the relationship allowed to fade, more intention put into seeing that friend.

It may be that I need to clean the house, clear the clutter, purge my closet. Or get my nails done, do my makeup slowly, take a walk. 

Sometimes it’s buying new clothing. Making an appointment at the dermatologist to truly heal your acne, or with a trainer to start strengthening your body with accountability. 

More often it's  choosing to declare your life is beautiful.

Being cautious with your negative thoughts, self-critical words, downward spirals. Clearing out the too tight clothes for a smaller amount you feel truly comfortable in.


[ jumpsuit: bhldn // shoes: bhldn // bracelet: anthropologie // watch: coach // rings: nicole vande zande // necklace: paisley + sparrow // photographer: kat harris // location: brooklyn, new york ]

Wearing a jumpsuit to that wedding because the pleated waist lets you eat cake without sucking in and the pants mean you can be free on the dance floor. Cutting a striking figure at the ceremony in gorgeous heels, then cutting a rug all night in bare feet.

Catching the bouquet (who cares if you’re not single — free flowers!) and taking it home for a vase on your coffee table.

Beauty is comfortable.

Beauty is a choice.

Choose your joy.

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Room to Breathe


A few years ago I never would have worn this piece. I wanted everything to be fitted. Not tight all-over, but without realizing it, I had told myself that I needed to prove that I was thin; that if I wore clothes too blousy, baggy or big I would look heavier.

[Backstory, I was 20 pounds heavier at one point which at 5’4” and at the time a professional dancer going to work-aka-auditions in a leotard, was a tough season.]

Many women have the opposite instinct — if they keep everything a little roomy, layered, not too tight, they’ll make sure to never expose a back roll or stomach bump. As a stylist when I encourage them to wear clothes that simply flatter their shape, it feels like they’re showing too much rather than simply no longer making themselves look larger than they are.

Neither choice is better or worse. What I’m passionate about is simply disrupting, questioning, hopefully resetting and shifting the voices in our head about our style and beauty.

This is not the most flattering dress I own as far as my shape. But I’m betting you didn’t think that when you saw these photos? You saw a beautiful color, flowing fabric, a big smile? In fact, wouldn’t it be worse if your first thought was “she’s skinny”? Do you find your mind exclaimed “beautiful” while registering the colors, flowers, smile all superseding shape or size?

Unless you’re auditioning for the Rockettes [the day the executive director told me I looked skinny I was thrilled] or on a sexy date, why is how slim our shape appears the first thing we’re concerned with?

I know that’s a big question. And I don’t expect either of us to let go of it overnight. But I do have a theory, that if you start dressing more joyfully, more colorfully, you’ll receive more compliments that have nothing to do with whether or not you lost ten pounds.

[ dress: thrifted, amsterdam // shoes: boutique, gains // purse: street vendor, gains // belt: vintage, london // sunglasses: target // photographer: christophe serrano // location: gains, france ]

P.S. A few tricks from this particular dress:

  • Ignore sizes when shopping thrift or vintage

  • If it has shoulder pads cut them out [as I did here]

  • If it’s a size too big, try belting it

  • If it’s rather modest overall, you can get away with a lower neckline [especially if you’re small chested]

  • Those last two bullets are my Line and V principle: emphasizing the natural feminine shape of our cleavage and waist is flattering on every body

  • Remember the better you’re dressed or the more stylish you look, the more you can get away with, including a 2-sizes too large $10 thrifted dress in the French Riviera [wink]

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The Everyday Dress


I have a new every-dress. I found her while shopping in London and after weeks of traveling realized her versatility.

Step one: Keep it neutral. Black, navy or any jewel tone, camel — stick with a solid color to give it maximum versatility. [You’re much more likely to get tired of or self-conscious frequently re-wearing a print.]

Step two: Seek an unbelted flattering shape. I love a belt. I belt everything. I find it so flattering. Often when I put on tunics I find they’re unflattering on my stomach, a little too clingy. However this one seemed to fall away from the body beautifully, meaning I could wear it confidently sans belt. I used this as a beach cover up to throw over a bikini for breakfast, a modest nightgown to sit around with our friends for a nightcap, wore her day or night.

Step three: Which can be belted to change the silhouette. Then I would belt it to change up the feel. Sometimes that felt more casual or fancy, sometimes more or less sexy, depending upon what I paired it with, but regardless there was a second shape to give me more diversity.

Step four: Accessorize it up and down. I wore this with flats or heels, simple jewelry or my peacock feathered necklace. I paired her with a denim jacket and an emerald silk coat, a colorful woven beach tote or a sensible leather laptop bag. The neutral color and easy shape were like a blank canvas with plenty of room to play based on the city or scenario.

[  dress: and other stories // necklace: j crew // rings: and other stories // bag: boutique, paris // photography: xenia udalove // location: amsterdam, netherlands ]

Step five: Where her everywhere. She became my most worn and loved travel staple. She made up for not having an endless closet, by giving me a super classic item I knew I’d feel good in. And when I got home, she became the warm weather alternative to the easy pants and sweater I’d throw on to work from the coffee shop or home office. 

I love diversity, wearing new things, playing with color and pattern. But sometimes you just want a classic you know works, zero time analyzing, out the door and back to your fabulous life …

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A Style for Every City


Traveling throughout Europe for a few months I became aware that certain cities have a style aesthetic. Of course there are tourists, but if you pay attention you can spot the locals and start to see a trend.

In Paris the style is drapey, slouchy. It’s fashionable, they’re not drowning in their pieces, there’s a cool cut or hem or fabric happening. But everything nonchalantly says “Oh this? I just threw this on”.

I’ve heard this from multiple Parisian friends or ex-pats. French women rarely paint their nails, jewelry is minimal, clothing is mostly black. Beauty, should be effortlessly chic. Trying too hard is tacky. Parisian women put forth effort in looking like they just rolled out of bed. [wink]


Amsterdam style is black leather jackets, dresses and tennis shoes. It’s a feminine/sporty blend in a city of women bicycling to work, dinner and dates.

With weather that always tends to be a bit overcast and chilly, so you want that jacket on hand, yet since you’re riding a bike hitting at the waist is practical. Lots of black, white, gray — similar to the fresh spacious modern design of shops and home decor you find throughout the Netherlands.


In America, we embrace color, pattern, accessories and generally more diversity in our style. Most shop windows whether at a mall in the midwest or a trendy neighborhood in a big city show all of the above.

Of course some Americans prefer more neutral or simplistic style, but no one thinks twice if you show up in something bright, busy or bold.

One of the questions readers posed about travel: how to dress to fit in where you’re going.

On the one hand, I’m a fan of being you. (Muslim countries or places like cathedrals with modest standards of course being respected.) On the other hand, I think it can be fun to let yourself be shifted and shaped by a new culture.

When in Paris, I found myself seeing my closet with that ease, embracing messy hair, leaving my accessories at home. 

Meanwhile in Amsterdam, I maintained my belief that I’m just not a black leather jacket kind of girl.

However, I sought out more neutral color combinations and that feminine/sporty blend — an athletic tank with a 50’s skirt, edgier booties, a bold stripe in an easy slouchy style.

[ tank dress: thrifted, paris // skirt: vintage, brooklyn // sweater: urban outfitters // boots: dsw // necklace: boutique, brooklyn // hat: street vendor, paris // photographer: xenia udalove

There’s nothing inherently refined about blending in.

Standing out can be confident. Your unique style can inspire someone else in their own country.

Yet I love the fresh inspiration of new places, styles, and ideas.

It’s that combination — your unique style blended with the people, places, experiences that only you have encountered altogether — that creates a style just for you.

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Pink Outside The Box


I used to hate pink.

I’ve always been feminine, but sure to distance myself from that girlie girl aesthetic -- Charlotte in Sex and The City, boutiques with “keep calm and buy more shoes” mottos next to tiara decor.

My feelings about pink were a story I had created.

Which is valid. We all create stories. And sometimes we should listen to them. Your friend could think that floral dress looks amazing, but if it reminds you of your grandmother’s curtains …

You can either choose to stand strong in one way — “No matter how chic, it’s always going to make me feel dated, it’s a no.”

Or you can choose to stand strong in another way — “I guess I used to see floral as grandma, but now that I think about it I keep earmarking floral dresses in magazines, noticing it on other women at work, so maybe my desire have changed.”

A couple years ago, I started craving pink. Color palettes in every combination of blush, peach, coral, tangerine, watermelon, raspberry, red had me swooning. [I feel happy just writing that sentence.]

I’d grown up. Perhaps I became more confident in my maturity, in my ability to put together chic outfits that had nary a hint of princess or prissy Upper East Side.

I realized I love the way the color looks against my blue eyes, my brown hair. And especially the pairing of multiple hues together — the freshness of color blocking, of two hues combined in tops and bottoms or stripes or accessory pairings.

Question your stories.

You’re not the same woman you were six years ago or six months ago.

Perhaps there’s some pieces in your closet that need to go. You used to be a girl who wears pink. And now you haven’t in years, but not noticing, those items are still sitting there slowing down your morning outfit decisions.

top + skirt: thrifted, paris // belt: thrifted, london // shoes: sperry top sider // photography: federico guendel //  location: paris, france ]

And perhaps there’s more color, pattern, delight waiting for you if you’ll just pause when your brain thinks “I don’t wear yellow, I can’t do stripes, I’m not a dress girl” and ask yourself “Are you sure? Why?”

See if perhaps the more mature you, has the confidence or craving to make something old new again.

Tay says shake it off, I say shake it up. Your stories, your thoughts, your combinations. You can wear and love so much more than you believe you can right now.

Take it from the anti-pink girl draped in blush, peony and magenta, feeling marvelous on a picnic with Beau in the shadow of Notre Dame ...

P.S. Are you a fellow entrepreneur, small business owner? Or dreamt of being a freelancer, maker, working for yourself?

In not just your style but vocation it might be time to question your stories and embrace a new season of maturity. If that sounds like you check out my free workshop How to Get Paid to Be Creative.

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A Place Of Yes



You see the woman walking towards you, “I love what she’s wearing” you think, quickly trying to decipher what exactly it is that makes her look so chic.

This simple afternoon on the Italian Riviera ensemble has multiple style principles occurring -- fabric, neutral colors, the waistline, the neckline, the skin tone, the accessories.

In the flash that she’s passed, you’ve likely not catalogued them all, or maybe none in the visual overwhelm of loveliness.

These aren’t rules as in “don’t break them”, they’re principles as in “use these as your secret weapons if you so choose”.

If you don’t know them, you’re not necessarily doing anything wrong, you simply don’t have your full range of motion. My desire is for you to stretch out your arms to the full breadth of possibility when it comes to what you wear.

One example in this ensemble: Yellow.


“Love it, can’t wear it” think most women. Myself included for years. But I believe you can wear almost anything you want, you just have to wear it in the right way.


Three ways to pull off any color:

1. Try different hues. Not all shades of yellow are created equal. Be you fair, olive or dark skinned, blonde or redheaded, some look more lovely or more like you’re slightly seasick.

2. Wear it away from your face. A skirt, shoes, purse.

3. Pair it with a color that flatters you, which is why I’m wearing a beautiful turquoise necklace.


top: thrifted, longod // skirt: vintage, brooklyn // necklace: street vendor, italy // shoes: dsw // photographer: erin + gabri // location: santa margherita, italy ]

Now yellow is not the secret to happiness or chicness. It’s simply today’s encouragement that you can wear more than you think, you simply need to understand the principles at play, and learn some secrets from your personal stylist.

Life’s too short to not wear all the colors in the rainbow, if they make you happy.

Stick with me and I’ll teach you when it comes to your style, in the words of Obama, “Yes we can”.

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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. Another way to say the above? My trademark 2-Part Fashion Cocktail. These pants were the vodka that gave a kick to my otherwise neutrals (aka cranberry) suitcase, making the perfect recipe for easy classy Italian days.

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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