Two Stylish Gents, One Incredible Italian Engagement

“Stylish” doesn’t even begin to describe the engagement session of Tom and Tim. In fact, these two gents took their impeccable sense of fashion and paired that with the backdrop of Tuscany for absurdly romantic photos captured by Rebecca Yale. Join us on their trek through Italy with lots more right over here.

From Rebecca Yale Photography My favorite thing about engagement sessions is they get to be a little slice of life so is there anything better than a destination engagement session which can perfectly capture the memories of an incredible trip exploring the Tuscan countryside? I spent a lovely Fall weekend photographing the incredibly sweet (and fashionable) Tom and Tim at Il Borro, a 1000-year-old castle estate, and medieval village in Tuscany owned by the Ferragamo family.

Tim, a former bronze medalist Olympic Ice Skater, was celebrating his master’s degree from NYU and of course their recent engagement. Tom popped the question at the historic Chanler in Newport, RI, where the couple will say their I Do’s next year. The trip was spent wine tasting, sightseeing in Cinque Terre, truffle hunting, shopping and eating way too much incredible Italian food. Minus a little rain in Cinque Terre we lucked out with a perfectly gorgeous Fall weekend, getting to enjoy the bright red leaves crawling up the wine caves and the perfect little breeze as we explored the medieval town.

The Proposal

From the Grooms… Planning an engagement proposal is very involved as there are many moving parts. For Tim and I, it started about 18 months before I actually proposed. In a non-traditional move, I mentioned to Tim that one day I could see us getting engaged. However, it would happen only after he went back to school to pursue a Masters in his field. With the proposal out there, I assumed it would be at least two to three years before we would potentially have serious conversation around being married; after all, at this time, marriage equality wasn’t even passed in New York yet and it was well before the Supreme Court decision made same-sex legal across all 50 states. But, Tim applied and was accepted into NYU Stern’s Masters program by that Fall 2015.

During the time that Tim was in school, I spent a great deal of time looking into unique options for a potential engagement. Ideas ranged from watches to cuff links, to bands, to an actual diamond, to just words. At the end, I worked with a jewelry designer in designing a unique diamond ring for Tim for our future engagement. This process took six months from start to finish. With the ring completed in late March 2016, I reached out to his parent’s to schedule a weekend together in early April while Tim was preparing for a series of exams with his programs. I arrived at his parents’ home in Arlington Heights, IL with a bottle of champagne and ring in box. His parents had a very strong idea of why I was there as their smiles were cheek to cheek upon walking in. Tim wasn’t aware that I flew to be with his parents for the weekend specifically; I mentioned that I was in the area for work and figured I’d stop by and spend time with them while he focused on his school work.

I asked Tim’s parents for their blessing to have the honor of asking Tim to marry me. His parents were beyond excited and we began celebrating from that point forward until that Sunday, which is when I headed back to New York to see Tim. Tim asked what exactly I was doing with his parents that weekend. I noted we were shopping for his graduation gift. So, upon returning home to New York on Sunday afternoon, Tim demanded that I share with him what I brought back for his graduation gift from his parents. The only thing I brought back was his ring.

Tim insisted on seeing the gift and went through all of my luggage. Fortunately, I had the ring in my pocket. I realized at this time that I was not safe in our home with the engagement ring – and with time, he was going to find it. So, we went for a long walk along the Hudson River. We ended up walking to where we first had cocktails together, Orient Express. We were the first guests of the day as they opened at 5:00pm. We ordered a cocktail and Tim inquired about his graduation gift from his parents. I started to laugh; I had no choice because of what I knew and he didn’t. Also because I was pretty sure that my perfectly planned proposal was about to be replaced by an impromptu proposal. Tim looked at me, grinned and asked what was so funny. I turned to him, took his hand, went into my pocket to pull out “nothing” and ask for his hand in marriage. Tim looked at me and sternly said, “this is not funny. You have repeatedly asked bent down on your knee before and proposed, you have repeatedly asked him in public for my hand, and you’re doing it again.” To which I replied, you’re right. Let me try one more time. So I went back in my pocket to search for the ring (mind you, I couldn’t find it in my pocket the first time as it was stuck in the crevice of the pocket) and presented Tim with a ring and a request for his hand in marriage. Tim was in shock and couldn’t believe it had actually happened. But it did. We toasted over another round of cocktails and made our way back to Perry Street to celebrate.

It wasn’t the proposal that I had spent the past few months planning in advance. However, I wouldn’t have changed it for the world as it brought us full circle from where we first fell love in one another to making our relationship “official” with a proposal.

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Photography: Rebecca Yale Photography | Rings: Custom by Anari Jewelry | Belt + Boots: Salvatore Ferragamo | Black Blazer: John Varvatos | Blazer (Cinque Terre): Hugo Boss | Boots (outfit 2): Gucci | Film Processing: Richard Photo Lab | Grey Blazer: Ermeneglildo Zegna | Jackets: Salvatore Ferragamo | Jeans: AG Jeans | Location: Il Borro | Pocket Square: Hermes | Sneaker Boots (outfit 2): Salvatore Ferragamo | Sweater: Ermeneglildo Zegna | Vest: Ermeneglildo Zegna | Watch: Cartier | Watch: Rolex | White Shirts: Thomas Pink

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{ The latest from our most exclusive, hand-picked list of vendors }
Jewel Tone Garden Wedding With Shades of Blush + Berry

It’s no secret we love a berry colored wedding palette any time of year. So when Jose Villa sent us this insanely gorgeous affair designed by Joanne Lue Events…let’s just say it was hard to keep our cool. Featuring elements of wood and stone, hand-dyed linens, ceramic dinnerware, and sweet personalized notes to each guest, there are so many take-aways to inspire a bespoke celebration of your own.

Al Fresco

From Joanne Lue EventsMeeting a couple like Jess and Matt was a dream – worldly and humble, the two met in business school in Philadelphia and fell in love during their travels around the world and shared a sweet bond over a love of music.

The two live in San Francisco so much of their design inspiration came from Northern California influences – raw and organic elements of wood and stone, hand-dyed linens from Silk and Willow, and ceramic dinnerware from The Ark Rentals, all beautifully shot by Jose Villa.

Their wedding was personal and intimate – Jess and Matt hand wrote individual notes to each of their wedding guests that were tucked into each escort card. As a nod to their love of live music, they named their tables after the many concert venues they had been to together over the years. Guests dined among hanging candlelight, bold jewel toned florals from Cherries Flowers, under an arbor of hundred year old trees. Dinner was a true farm to table feast with tomatoes picked directly from the on-site gardens. And as frequent hosts, Jess and Matt indulged their guests with their favorite foods – cupcakes in lieu of a wedding cake, gourmet bread baskets served with multiple flavors of butter, polenta, and desserts from Jess’s childhood of sesame mochi.

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Photography: Jose Villa Photography | Cinematography: Daniel Chae | Event Design: Joanne Lue Events | Event Planning: Joanne Lue Events | Floral Design: Cherries Flowers | Wedding Dress: Leanne Marshall | Cupcakes: Sibby's Cupcakery | Bride's Shoes: Jimmy Choo | Bridesmaids' Dresses: Jenny Yoo | Catering: Paula LeDuc Fine Catering | Hair + Makeup: The Glamourist | Lighting: Got Light | DJ: Boutique DJs | Groom's Attire: Canali | Venue: Paula LeDuc Fine Catering | Bride's Accessories: Perfect Details | Furniture Rentals: Bright Event Rentals | Furniture Rentals: Classic Party Rentals | Invitations, Stationery + Calligraphy: Oh My Deer Handmades | Linen Rentals: La Tavola Fine Linen Rental | Silk Accessories: Silk & Willow | Tabletop Rentals: Frances Lane | Tabletop Rentals: The Ark Event Rentals

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3 Ways to Rock a Conflict Free Diamond on Your Big Day

One thing we know for certain? Finding the right diamonds for THE big day is an absolute art form. Especially if you are in search of conflict-free jewels that are as eco-friendly as they are beautiful. So today we’re turning it over to our friends at Ada Diamonds for three tips on rockin’ lab grown diamonds on your wedding day… and beyond. Find out how below.

Start with the Ring

First step? Find that conflict-free engagement ring that will make your heart happy. Think breathtaking, bespoke diamonds that are everything you’ve ever wanted… and so much more. With Ada Diamonds, you can create that dream, absolutely-can’t-stop-staring-at-it ring with a diamond that is chemically and structurally identical to mined diamonds, yet socially and environmentally friendly in ways that mined diamonds aren’t. We love.

Make It Official

It starts with the engagement ring, but Ada Diamonds’ made-to-order wedding bands for men AND women are just as beautiful. I’m talking colorless diamonds, fancy colored diamonds and gorgeous metal options, like platinum, white + rose + yellow gold and black rhodium gold. Ada Diamonds can even duplicate an existing wedding band to make an anniversary band! Ada Diamonds also offers their unique Strong Collection featuring rings made of a polycrystalline diamond material, Polydiamond, that makes every. last. piece in the collection seriously strong and unscratchable. In other words? All of the options are absolutely stunning AND an awesome + vegan friendly way to say “I do” to your special someone.

Don’t Forget the Other Bling

Your ring finger isn’t the only place that deserves a little diamond love on the Big Day.  With Ada Diamonds’ Delicate Collection, those conflict-free cultured diamonds can make an appearance as necklaces, earrings and bracelets, as well.  Not to mention that they make a perfect gift for your bridesmaids, mother and soon-to-be mother-in-law… whether that’s on wedding day or a special something for the holidays!

Visit Ada Diamonds today to find that special piece of conflict-free jewelry that you’ve always dreamt of. Your eco-friendly ring? It’s waiting, loves.


Don’t forget to use the code STYLEMEPRETTY10 for 10% off any the Delicate and Strong ready-to-wear collection pieces at Looking for a bespoke piece? Mention the coupon code to your Diamond Concierge during the design process to receive 10% off your entire fine jewelry order. Happy shopping!

Minimal Wedding Details That Pack a Stylish Punch

Whether big or small, weddings these days are all about the details and we’ve fallen big time for celebrations that merge minimalism with the modern day soiree. Think monochromatic blooms with a modern twist, or added texture with gorgeous greenery and wildly beautiful bouquets styled to a T. From clean lines to luxe materials, we’ve rounded up how you can get the ‘minimal’ look without sacrificing major style on your big day.



The Reception

The Seating Chart

The Invitations

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