From beautiful Boston, Massachusetts


To my friends and family, I'm Lyss. Welcome to A With Love, a space where I've weaved together my passion for Mediterranean fashion and food in a way that I hope inspires you in areas of your own life.

WELCOME, I'M alyssa!

Tips for Deciding What to Wear for Engagement Photos

I am so excited to finally be sharing our full engagement session with you. We shot our photos with Rachel Leiner (a dear friend of mine who also takes many of the photos you see here on the blog) back in mid-September. We drove up to Wingaersheek Beach in Gloucester, Massachusetts to chase golden hour for our seaside shoot, a final hurrah before bidding summer farewell. It was truly a magical evening filled with cotton candy skies and calm waters, a serene and utterly romantic backdrop for the occasion. Matt and I have been engaged since late August 2019, so by the time our session rolled around, we’d officially reached the one year mark until our wedding day.

Before I continue on with our engagement session and sharing my tips for how to choose the perfect outfit, I wanted to share a brief recap of our proposal story, because I don’t think I’ve ever shared it here –

Matt proposed during a long weekend trip on Cape Cod. West Dennis Beach, to be exact; a beach that I’ve been very lucky to spend every summer on with my family since I was born, while staying with my grandparents at their cottage in Dennis Port. It came as a complete and total shock to me, even though we’d celebrated our eight year anniversary just a month prior. I remember leaving the office the Friday before and my friend and then-coworker, Lauren, said to me, “I’ll see you on Monday ….with a ring.” I thought she was being crazy and brushed it off (come to find out, it was just a lucky guess!). At the time, Matt and I had been on the umpteenth month of going to open houses in search of our first home, and I thought it would be another year before he asked.

We had been vacationing for the long weekend with my sister and her boyfriend and were headed to the beach for wine and cheese while we watched the sunset, something that was fairly routine for us before heading to our dinner reservation (we had done it the night before, too, which now I realize helped to lay the groundwork for the plan). I was sitting on the picnic blanket when Matt got up and asked me if I’d take a photo with him. This was a normal ask, but I was busy eating (lol) so I asked if we could do it later. He kept insisting and I got increasingly annoyed (I feel so badly about that, now, but I had to share this to illustrate how truly caught off guard I was by this). When I got up and he got down on one knee, my brain was very slow to catch up with what I was seeing. It wasn’t until I turned around to see Rachel (she’s been there for all the big moments!) with her camera snapping away, that I realized what was happening.

I kid you not, I think I blacked out after that. It was truly an out-of-body experience, and one I wish I could relive, mostly so that I can remember. Matt had to text me his speech afterwards because I hadn’t heard any of it. HA! Clearly, I am not one of those people who is great at being on the receiving end of surprises, especially one of such magnitude. One thing I do remember, is that Matt didn’t appear the least bit nervous. It wasn’t until we sat down at dinner that he welcomed a tall drink, at which point it became clear just how much he’d been internalizing that day, and likely the entire month leading up it (which he spent most of planning logistics with my sister).

After FaceTime-ing with our families, we headed to one of our favorite spots in Dennis, The Oyster Company, capping off the night with a delicious champagne and seafood dinner. The next morning, we packed up our things and headed home to a surprise engagement party thrown by both of our families at Matt’s parents’ home. Both of our maternal grandmothers got to be there, too, which was so special for us. We were able to replay the video my sister took while the proposal was happening, for them to see. It’ll always be one of my favorite days.

Choosing what to wear for your engagement session certainly can be a daunting one! It took me many months of online searching to find my dress. I had a very specific vision for the overall vibe of our session, right down to the time of day. In my experience, it really helps to determine a location prior to looking for an outfit. Let the backdrop of your photos help guide your style choices. Matt and I love the beach and wanted our photos to commemorate the location of the proposal, even if we couldn’t get to the Cape due to scheduling and certain COVID restrictions. Gloucester was the next best thing, known for its vast and beautiful shorelines. Given the time of year we were going to be shooting, we knew the beach would be somewhat empty, so we didn’t have to feel awkward posing in front of strangers. We were comfortable and able to be ourselves, which I believe always makes for great photos.

While style and vibe for any wedding-related events boils down to your own personal style and preference, there are a few key tips I’d recommend you to keep in mind when looking for and deciding on what outfit to wear –

1. Know what makes you feel confident. For me, that comes from the structure and cut of a piece. I searched high and low for an off the shoulder dress with a structured bodice, because I know that I always feel great in this style, and that it flatters my figure, highlighting my broader shoulders and décolletage. If dresses aren’t doing it for you, try a two-piece suit combo with an ultra-feminine, tailored fit. It’s a total power move, IMO, especially when paired with a a chic pointed pump. There are no rules when it comes to what makes you feel confident from a style standpoint. When you feel good, you look good, and that confidence will definitely translate into your photos.

2. White isn’t the end-all, be-all. Just as a dress may not be your style, the all-white ensemble may not do it for you, either. Depending on the season you’re taking your photos in, choose a color that better compliments your backdrop (red, black, or gold for the winter months, a beige, brown, or off-white for autumn, etc.).

3. Buy your usual size, plus a backup. I can’t recommend this move enough. When I bought my dress, I’d never worn the brand before and was wary that due to the tighter bodice, my usual size might not cut it. I ended up buying the same dress in two sizes and returning the second that didn’t fit as well. In the same token, you could always buy a handful of different colors and styles, if you have don’t yet have an idea what style or vibe you want.

4. Consider splurging. This one will of course depend on the person and your view on spending, but I say this because you will have these photos and memories forever, and when you look back on them, you’ll want to love them as much ten years from now as you did the day you took them. In many cases, a more timeless garment costs more, whereas a trendy piece may not. If you can’t justify the expense, renting is always a great option.

5. Try to compliment each other’s outfits. I’m not talking high school prom style, but some level of coordination when it come to your and your significant other’s outfit can really make or break the overall theme of your photos. Matt and I still remained true to our individual styles while making a concerted effort to compliment the colors and materials of both of our looks. I wore a white cotton peasant dress, while he wore dark-wash jeans and a pale blue, collared button-down shirt. The shirt and jeans were slightly rolled up at the cuffs for a beachy, laid back look.

Below are some of my favorite traditional and non-traditional bridal looks for you to comb through as you plan your own engagement session (or elopement), including the full outfit details I’m wearing above. I’d wear them all if I could, but then I’d have a million more photos, and we’re already having a hard time deciding which ones to frame! About my ring – Matt designed it himself with Barmakian Jewelers at their downtown location in the Jewelers building (it’s also where I go to get it cleaned and they do an outstanding job). My ring is platinum and a Bostonian three-stone cut, baring great resemblance to my mother’s ring, which I’ve always loved and admired.

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