What to Wear for a Holiday Engagement

What to Wear for a Holiday Engagement

Editor’s Note: This post is sponsored as the ruffled sweatshirt from Elizabeth Wilson Designs and the gold knot ring from Erica Weiner were sent to me complimentary in exchange for writing this post. All editorial and opinions are my own.

The holidays are a preppy girls’ best friend for engagement photos. You can pile on the tartan, cable knit, and duck boots galore! While it can be fun to play dress-up for photos, my favorite captured moments are those of couples in their comfy every day clothes. And let’s face it, it’s a lot easier to run and play in jeans than a full skirt or dress. With the help of Elizabeth Wilson Designs and Erica Weiner, I put together a laid back preppy ensemble perfect for a holiday engagement on the lake and I’ve outlined a few tips below to help ensure you snag the most adorable engagement shots you can!


Tip No. 1 | Comfort first!

Choose something to wear that makes you feel completely comfortable. Engagement sessions usually only last a few hours at most and you don’t want to spend that time tugging and pulling and re-tucking and sucking it all in – you’ll end up looking uncomfortable and stiff in your photos. I love the simple idea of a dressy ruffled shirt with jeans. The dressed-up sweatshirt by Elizabeth Wilson Designs I’m wearing in these photos (yes, I said sweatshirt!) is unbelievably soft and comfy but the plaid ruffled collar and bows on the back really elevate it a whole new level. Pairing it with pearls cinches the look.

Tip No. 2 | Bring more than one pair of shoes

Shoes can change an outfit drastically. While I love a good pair of Bean Boots, the power of heels is undeniable. Heels instantly lengthen and tone and that is definitely conveyed in photos. While it may be impractical to wear heels for your shoot, at least bring a pair along that look cute with your outfit and toss them on for a couple of shots. It can also be fun to just mix it up – whether you change outfits completely or just switch your duck boots out for a pair of monogrammed wellies or Hunters.

DSC_0088DSC_1539Tip No. 3 | Accessorize!

I like to keep my accessories fairly simple on a day-to-day basis with pearl studs and a few bracelets but for engagement photos, I recommend stepping it up and adding a few more items for visual interest. I love adding a little sparkle to my nails for the holidays and the shine and shimmer translates well on film. Adding a few rings can make a pretty statement, too. I adore the simple gold knot ring from Erica Weiner I’m wearing (shown above) because of the nautical vibe and the symbolism of tying the knot. These knot rings would also be darling gifts for your bridesmaids!


Tip No. 4 | Natural props

For a holiday engagement, I love the idea of incorporating holiday decor like wreaths and bows. I think some of the best photos come from natural moments so I would suggest simple activities like hanging a wreath and tying/fastening bows with your love. Just don’t forget to smile and laugh together while you deck the halls! If you’re headed to a lake or beach or even a park, consider bringing some of that pretty decor with you. A Christmas wreath or kissing ball can add a lot of color and texture and it really emphasizes the holidays.


Photography and styling by Sarah Darcy of Classic Bride blog.