
Whether you’re browsing my classic style favorites, daily looks, or capsule wardrobes, one brand that you’ll see again and again is Tuckernuck. I’ve been inspired by this clothing retailer for over ten years. Their mix of timeless designs and trendier pieces at various price points makes it almost impossible not to find something I love each time that I open their website. And while I’m a fan of all things Tuckernuck, from their shoes and jewelry to their clothing and gifts, today I’m going to focus on one of my absolute favorite items, Tuckernuck dresses.
Not surprisingly, there are many Tuckernuck dresses that I absolutely adore. But for this post I’ve really tried to narrow it down to ones that I wear and re-wear on repeat. Below you’ll find my top 12 favorite dresses for every occasion, ideas on how to style them, and my honest thoughts on each.

About Tuckernuck
Founded in 2012 by Jocelyn Gailliot, Madeline Grayson, and September Votta, three powerhouses and visionaries, Tuckernuck is a go-to destination for all things fashion and lifestyle. Not only do they carry unique brands, but they also have in-house labels with beautiful designs. Their styles can be worn by teens and women of all ages. My mom is in her 70’s and wears them just as often as I do in my 40’s!
Tuckernuck’s motto is “find the fun”, and it’s so easy to do just that when you’re perusing their website. Their creative eye, impeccable styling, and helpful travel guides are all so inspiring. I also find the fun over and over again by wearing Tuckernuck pieces and changing out my jewelry, totes, and shoes to keep the looks fresh and fun!

Tuckernuck Dresses Sizing
Before jumping into my favorite Tuckernuck dresses, I wanted to share a quick note on sizing. For the most part, I’ve found that their styles fit very true to size. I wear my normal dress size, an XS, in all of them, with one exception. In my opinion, the Chloe Dress runs a little big, so I sized down to an XXS in that one. For all of the others, I would recommend your normal size!
Top 12 Tuckernuck Dresses
Okay, now onto the fun part! I flipped through my closet and pulled out all of the Tuckernuck dresses that I own and love, narrowed it down, and came up with what I consider to be the top 12. One great thing that all of these pieces have in common is that they’re versatile and classic styles that can be worn year after year in so many different ways.


The Esme Dress
Let’s start with one of Tuckernuck’s newer styes—the elegant Esme dress. The moment I saw this one it was love at first sight! I adore the length, the way it flows, and the timeless shape. It features a fitted square neck on top with a flattering full skirt on bottom. And it has pockets! It’s a great dress for a wedding, gala, or any formal event.
The Delaney Dress
If you love a fun, flirty piece, the Delaney Dress might be the one for you! This Tuckernuck style has cute puff sleeves, a fitted waist, pockets, and lots of great color and print options. Plus, it’s available in two different lengths, mini or midi.
And at under $150, the price point is excellent! It’s one of those dresses that you’ll wear to Sunday brunch, a beach vacation, or family pictures. My mom actually borrowed mine for our family photos this year!



The Chloe Dress
One of my all-time favorite Tuckernuck dresses is the ultra chic and timeless Chloe Dress. I own this style in three different color schemes – red, black watch plaid, and a blue floral. It’s that good! This dress is something that I could see classic style icons from 100 years ago wearing just as seamlessly as women wear it today.
While it is a dressier piece, and your first instinct might be to wear it with heels and statement jewelry, I’ve found you can also wear it more casually with flats. Last year I wore the red version to a family viewing of The Nutcracker and then a few months later I wore it again on Valentine’s Day. And as I previously mentioned, this is the only Tuckernuck dress that I think runs a little big.
I was thrilled to see that Tuckernuck recently released a mini dress version of this silhouette! Such a fun take on one of my favorites.

The Callahan Dress
The Callahan is one of the most versatile and easy-to-wear Tuckernuck dresses. It’s a classic shirt dress, with a few twists! The buttons only go about a third of the way down, there is a fun flounce hemline, and it has functioning side pockets. These details help take the timeless shirt dress design to the next level!
This is one of my most-worn dresses. I really love the length and the lightweight comfortable fit. It’s a style that I know I can always count on to throw on and feel confident in, no matter what kind of day I’m having.
For this reason, there’s always a Callahan Dress crisply ironed and ready to grab from my closet! I often wear it when I’m volunteering or going to a school lunch. But it’s great for everything from a shopping day with friends to a date night, just change your shoes and accessories!



The Jackie Dress
Inspired by style icon Jackie Kennedy, the tweed Jackie Dress is the perfect blend of vintage vibes with modern touches. This dress comes in many different color options, all on a quality tweed fabric. It features braided details, gold buttons, and an effortless shift silhouette.
The instant I put it on I always feel elevated and stylish. So when we had dinner at Cafe de la Paix in Paris last year, I immediately knew this was the right dress for such a special occasion. It just felt right! I’ve also worn the Jackie Dress to luncheons, closing chapel at school, and more. It’s a great staple to have in your closet.

The Royal Shirt Dress
One of the most popular Tuckernuck dresses is the Royal Shirt Dress. In my opinion, this is the very best “throw on and go” piece. It instantly makes you look cute and put together with minimal effort. This is another style that I love so much that I own it in multiple colors and patterns. It looks great with sandals, sneakers, flats, or heels!



The Cornelia Dress
The Cornelia Dress is a classic chambray dress with some fun twists! It features a charming ric-rac trim and a flattering tie waist (which can also be removed). This is one of those styles that can be worn for so many different occasions. I’ve paired it with sandals and sneakers for casual school events, and I also plan to dress it up with heels for nights out.

The Maryse Caftan
I love the comfortable fit of the Maryse Caftan. This is a style that I’ve had for years and still pull out of my closet. The material is a bit sturdier than most caftans I own, making it a great transitional piece for early spring and late fall. This dress looks great styled casually with sandals or dressed up with heels!



The Collier Dress
The Collier Dress is a summer staple in my closet. It’s a simple, yet elevated mini that instantly makes me feel put together. I love the beautiful details including a classic spread collar, fun 3/4 length sleeves, and stunning print options. This new brown lace version is on my wish list!
The Marlowe Dress
If you’re like me and love a shift dress with vintage vibes, the Marlowe Dress is a must. I like to call this my Maxine Dellacourte look! It’s great for a baby shower, date night, or graduation ceremony. And once again, the Marlowe proves that Tuckernuck dresses can be worn by women of all ages. I could easily see college girls wearing this silhouette as well as women my age and older.



The Brynn Skirt
Okay, I know this isn’t a dress, but Tuckernuck’s Brynn skirt is such a great staple piece that I had to include it. This is one of those truly timeless styles that I’ll still be wearing 5+ years from now. It pairs beautifully with everything from tanks and tees to blouses and sweaters.

The Emerson Dress
Lastly, the Emerson Coat Dress is a wonderful fall or winter dress to add to your collection. Made from a thick and cozy material, this one looks great with your favorite pair of boots. I love the equestrian vibes of this dress, with its button collar and elbow patches. It’s such a fun take on a classic!

sThe Best Tuckernuck Dresses
This retailer is always a go-to shopping destination for me, whether I’m looking for vacation clothing, classic staple pieces, or even gifts for her. If you have any additional questions about these Tuckernuck dresses, feel free to send me an email!