Before you get overwhelmed and think “this is just another stylist’s holiday guide with a million links and a million items to contemplate buying”

let me reassure you that this is meant to organize your brain, organize your life, and make you feel confident with the purchases you were already eyeing or planning to make in the next few months.

I would like to note that I am not a trend forecaster and these are not future predictions on what is going to be “hot” this season. This guide was built based on what’s already happening and WORKING in the market. The fashion world can be hard to digest - there is truly so much going on, season after season, year after year. It can be difficult to decipher what to invest in.

We want to know our purchases aren’t just for one Holiday season and next year we won’t find these pieces shoved to the back of our closets - I can assure you these are trends that have either proven the test of time, were loved by many in years past and are now continued variations, or these are maybe newer trends that I believe we will continue to see for the next few Holiday seasons.

With that being said chances are, you may already have your eye on a few of these pieces!

I’m just your friend here to tell you, you’re on the right track and you should invest in yourself. We all deserve it. This time of year is magical but it can also be stressful. I want you to think of reading this guide as a form of self care. Self Care before we spend all of our time thinking of others.. before our thoughts are consumed with ‘What to cook when hosting our family for the holidays’ , ‘what to gift our loved ones’, ‘what the perfect gift is for our Holiday work party..’ In a way, this is the ANTI-holiday gift guide. This is for YOU. This is for you to pour a little magic into yourself, which in turn will allow you to pour magic into others.

What! You have to admit, you’re always happier in a fabulous new look.

I have broken out this style guide in 8 key ideas. These key ideas are forward yet relatable - I truly believe there is something for everyone. Whether you’re an early adopter and have been wearing these trends for months now or you’re on the fence about pressing send on a certain look because you’re not sure how to execute - this may be the push you need to have the confidence to rock a new look that’s a bit out of your wheel house.

From there, I go with the 2 of 3 rule. There’s 1. identifying personally with a key idea, there’s 2. LOVING an individual piece, and there’s 3. having a need in your wardrobe for a piece. If you say yes to 2 of 3 - it’s likely a great purchase.

Like I mentioned, you will find a little of everything in each category. From pajamas to occasional dressing to après ski looks to wear-to-work to many more.

Something I tell all my clients, is that personal style is a mix of what brings you joy and trends that you adopt into your everyday life. That is the purpose of trends, for them to find a home. Of course we all know that not all of them are here to stay - for everyone. But some of them could be here to stay for YOU. It’s knowing which trends will ADD to your wardrobe and those that won’t. After all, that is why brands bring them into their collections - year after year, they are trying new ideas, new silhouettes, to see what resonates with their ideal client.

Brand Identity. Consumer Identity. It’s all one big ever evolving circle.

Your wardrobe should be carefully curated to express who you are as an individual. So without further ado - let’s get into it!

Dark Chocolate Brown

We all want to feel rich and sweet!

Oh boy. Brown - I learned the industry used to say “Brown - Mark it down.” For years - I think everyone was hesitant to fully accept the color. I’m not sure everyone was fully convinced it was going to work, but I’m here to say brown is here to stay. Whatever your complexion, whatever your hair color - dark brown will only do wonders for you. It’s rich and elevated and the color itself just gives “cool” and “effortless”.

Below are for of my favorite ways to incorporate an all brown look. From a black tie event, to a night out with the girls, to a Holiday work event to a casual but fabulous Apres Ski day.

For all the pieces above and more Dark Chocolate Brown - shop here! https://shopmy.us/collections/public/1000686

The Gucci Girl

The ‘Casual Grandeur’

Did Gucci ever go out of style? Of course. I won’t lie, I think the brand has had it’s moments. Sabato De Sarno’s year at Gucci hasn’t been the strongest but his Spring 2025 collection gave us all the future inspiration we will need. It was solid and saleable and honestly a hit, in my opinion. Who knew throwing burgundy on literally everything and reverting to simple square necklines would influence the entire market? He mentioned in a Vogue article he was inspired by the Gucci girl of all Gucci girls, Jackie O. Who was described in this article as “The Casual Grandeur.” I thought that was a perfect way to describe the brand. Gucci to me has become a version of what we all want to be. A personality. Refined but bold. Scholarly but carefree. Chic but in a intricate way. From the thick frame black glasses, to the signature plaids, to the lurex in all of the accessories, the iconic horsebit fastener, the loafer and everything they’ve done in between. It’s 60’s. It’s 70’s. It’s modern. It’s the maximalist’s perfect Holiday dream.

Of course, we can’t all afford to be a full blown Gucci Girl - luckily so many brands have been inspired by Gucci over the years and the effect has been long lasting. I’ve pulled a mix of inspiration, vintage, and current Gucci in the looks below. From a Black Tie event, to a Holiday lunch and shopping day with the girls, to Holiday party’s whatever the attire -

For all the piece above and more Gucci Effect pieces - shop here! https://shopmy.us/collections/public/100037

The Teddy Bear Effect

Hibernation Here We Come!

I can’t even imagine not being instantly attracted to any fluffy item of clothing or shoe or accessory that crosses my path. Faux fur, real fur, Mongolian wool, feathers, shearling, whatever your choice in fluff - it’s here and it’s here more than ever before. RESPECTFULLY, IT’S TAKING OVER. AND I LOVE IT. Believe it or not, there’s a math behind incorporating said fluff - there’s 2 main forms of looks that I incorporate the fluff - I call them ‘minimalist chic girl’ and ‘the ultimate weekender.’ The minimalist chic girl is wearing sleek fabrics (chiffon, cashmere, silk), easy to understand silhouettes (turtlenecks, crew necks, lounge like maxi or midi dresses) and monochromatic color schemes.. The fluff is the moment, but the fluff is adding an element of approachability while ironically being the focal point of the whole look. The fluff is making you look THE PART. The ultimate weekender is wearing relaxed and breathable fabrics (denim, cotton, jersey), casual silhouettes (baggy jeans, t-shirts, stirrup leggings) - the fluff is dressing up the look in a different way here, it’s making you look like a warm hug and extremely inviting. Either way, you can’t go wrong by adding fluff to your holiday wardrobe.

For the pieces above and more from the Teddy Bear Effect - shop here! https://shopmy.us/collections/public/1000654

The Chemena Effect

Redefined & Refined - Boho is Back!

We all know Boho is back ever since Chloe’s creative director Chemena Kamali gave the brand it’s identity again - but I’m more focused on Chemena herself this holiday season. To me, she is the ultimate Chloe girl. She has the element of nostalgia and emotion that we can all relate to. She’s a wife and a mother of two - she makes the idea of ‘Boho’ wearable for women everywhere. She gives those of us who were infinitely fascinated with Tumblr in 2012 a new way to adopt the trend, in these vastly different phases of our lives. She gives ‘boho’ the meaning of being free and youthful while still nostalgic and whimsical. In a way this ‘Boho Chic’ aesthetic is the updated ‘Sugar Plum Fairy’ aesthetic this Holiday season and I’m so here for it.

From a winter bridal moment, to Holiday work parties, fancy date nights with a special someone, or just a an upgrade to your winter work wardrobe when you feel like adding that sparkle to your day.

For these pieces and more from the Chemena Effect - shop here! https://shopmy.us/collections/public/1000473

Winter Whites

We all want to be Cam Diaz in The Holiday

There is truly no better feeling than wearing ivory during the winter holidays. Cashmeres, wools, silks.. all which I own in ivory. Building a perfect monochromatic winter white look is the perfect way to look polished and fresh. There are so many ways to do this - I don’t feel like I need to go into too much depth on this topic - I’ll let the looks speak for themselves.

From a bride’s special evening, to a nice upper east side dinner with your significant other’s parents, to those fancy gala’s and charity events, to a weekend upstate vintage shopping with your girls.

For these pieces and more of the Winter Whites - shop here! https://shopmy.us/collections/public/1000435

The Drape Effect

We’re finally graduating from the neck scarf, ok?

As sad as my subtitle is, it’s true. I need us all to take a minute and step away from the neck scarf obsession. It’s chic but we can do better. We can try new things. It’s OKAY! For those who are quite literally devastated with this comment - and for everyone else who is not married to the neck scarf, I would like to introduce you to ‘the drape.’ She comes in all shapes and sizes. It’s the neck scarf 2.0. We are still giving that elegant movie star vibe but kicking up 5 notches.

From a GNO, to an iconic NYE look, to an European après ski look.

For these pieces and more from The Drape Effect - shop here! https://shopmy.us/collections/public/1001079

Suits & Ties

Time to Take Our Power Back - In and Out of the Office

When it comes to suiting, it’s tailored! Hallelujah! Finally. Gone are the days of the baggy suit. Not to say you can’t do one or the other - baggy suit pant with a tailored shrunken blazer. Cute. Skinny tailored pant with an oversized blazer. Also cute. But we are no longer going to look like Kid President in baggy oversized suiting. Giving it a sharp tailored look in a way makes this whole trend actually sexy to me. Women in button downs fully buttoned, fitted trousers, with a properly fitted blazer.. add in a tie and it’s like we’re here to say we’re in charge! It’s chic and cool, but elevated and feminine. This Holiday season when I throw on my favorite cropped cashmere sweater - I’m trading in my denim for a tailored pant, and instead of my oversized bombers I’m reaching for a quality fitted blazer over my favorite long dress, or even wearing it as a top with a long skirt underneath. We’re playing with shapes and structures here. We’re playing with the juxtaposition of masculinity and femininity. Women are taking over suiting and it’s so fabulous.

For these pieces and more from Suits & Ties - shop here! https://shopmy.us./collections/public/1000529

Tights, Tights, and More Tights

Your New Skin & Pants All in One

When it comes to tights - it’s a no brainer they are are a Holiday season must - but we’re expanding. I REPEAT, WE’RE EXPANDING. We’re now wearing every single color tights, we’re wearing embellished tights, we’re wearing sock versions of tights.. if you’re wearing a cropped pant - wear tights underneath with a cute open toe heel. Denim, Silk pants, Sweater pants, suiting pants etc. Any chance you can get, we’re learning a tight is only going to elevate the look.

For these tights and more from Tights Tights and More Tights - shop here! https://shopmy.us./collections/public/1001076

One final note, while I tried to source as much current ready-to-wear pieces as possible - I love my one-of-one vintage finds and you’ll find a few pieces through out these collections. After reading this if you are looking for anything specific always feel free to reach out so we can make some magic happen - style@jespressostudio.com.

With love, and happy holidays,

Jessi Girl