I'm Basically Living The IRL Version of 27 Dresses

Ever wonder how Jane Nichols (played by Katherine Heigl) felt zooming through New York City in a yellow cab, changing from a detailed orange and fuchsia saree to a lavender scoop-neck bridesmaid dress in 27 Dresses? Honestly, neither did I, until I lived it, meticulously juggling 14 nuptials this year alone (both as a guest and a member of the wedding party). Blame it on the postponed ceremonies, receptions, and engagement parties of the 2020-21 pandemic years, but your girl has been booked and blessed since January 2022. Friends have even joked that being a professional wedding guest is my new day job, and they’re not wrong. In the span of nine months, I’ve celebrated love in the following destinations: San Diego, Miami, Austin, Portland, Big Sky, Guadalupe, Sacramento, San Francisco, Milwaukee, Chicago, Cabo, New York City, and Los Angeles. The travel alone is exhausting, let alone coming up with multiple wedding guest outfit ideas.

Apart from the three I-dos in which I served as a bridesmaid (for which I was provided with style guidelines), I had to come up with different looks for each rehearsal dinner, ceremony, and post-wedding activity. Often, that meant I needed two to three photo-ready outfits for each event, all tailored to different climates and themes. In short: A lot of planning went into curating the perfect wardrobe for each wedding.

In an effort to spare my bank account, I rented most dresses from Rent the Runway and Nuuly, and repurposed tried-and-true favorites. What I loved about going this route is that, with my membership to both services, I was afforded a wide variety of options, including luxe gowns that would normally be out of my budget. Plus, I could purchase any designs I fell in love with at a highly discounted price.

Ahead, I’ve categorized some of my favorite dresses (+ two perfect pants set) from the past year by climate and theme. Keep scrolling to see them along with styling tips and links to shop or rent some of them — and similar styles — for yourself.

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For Fall & Winter

Autumn is one of my favorite seasons for a ceremony because you get to play around with transitional wedding guest dress options. I dressed outside the box with my Free People two-piece set in Portland, had an electrifying time on the streets of Cabo in my NastyGal lime green ensemble, and opted for a full-sleeve in Santa Barbara to combat bitter winds for evening I dos. While you can generally get away with sleeveless silhouettes in spring and summer, the key to dressing for September-through-November weddings is to look up the weather ahead of time. There’s nothing worst than showing up in an asymmetrical sleeve dress and shivering as the wind passes through you. It’s a good rule of thumb to keep a layering piece or light coat for fall and winter weddings in the event that the weather takes a turn. In other words: do your research.

For Spring

For the spring season, I attended weddings in New York City, Chicago, and Guadalupe, Mexico. Apart from the humidity in Mexico, the other two weddings saw chillier temperatures, so I decided to go with either a long-sleeve dress or party-ready coat to keep warm. And since my favorite part about weddings is dancing the night away with close friends, I always go for airy options that are comfortable and breathable enough to not show sweat. Every piece needs to give enough movement to really cut a rug. I, personally, appreciate a sleeve detail to add a little more oomph to an outfit and love a good statement dress. But if you’re more of a minimalist, you can always grab a slip or LBD and glitz thing up with accessories or accent heels.

For Summer

If you are attending an outdoor wedding (typical for warm-weather nuptials) reconsider your impulse to wear a maxi dress, as it could potentially be dragged through dirt or sand (stiletto heels, for that matter, often get stuck in the grass, too). And while it’s also important to check the dress code (formal, black-tie, etc), I find that summer weddings are more laid-back and don’t require as much of a show-stopper.

Apart from my stunning, free-flowing feather-y dress from Andreeva, this June, July, and August, I traded out accents and details for pops of colors that would highlight my sun-kissed skin. I opted for bright oranges, aquamarine blues, and lime greens that would shine in the sun, and fabrics like cotton, linen, and polyester that kept me cool despite the hot climate.