What to Wear for a September Wedding (or Three)

This September, due to a combination of pandemic engagements, rescheduling, and sheer chaos energy, H and I were invited to three weddings: one for my college friend in Cincinnati, one for H’s college friend in northern Virginia, and one for my cousin in Richmond. While the logistics of the month were daunting, I was beyond excited to celebrate these three beautiful couples with our friends and family and for one of my all-time favorite activities—choosing wedding guest dresses!

For starters, and if you read this blog you already know this, I LOVE weddings. I have loved weddings ever since I was little, and since H and I got married last year my awareness/adoration for weddings and other wedding-related events (showers, engagement parties, minimonies, rehearsal dinners, etc.) has only escalated. For me, choosing a wedding guest outfit is a fun project—I gather intel on the location, the venue, and the time of day, and then I figure out what to wear that will match the wedding’s vibe without being too expected. So, starting in May when we realized we had back-to-back wedding weekends (plus one free weekend, during which we started the process of buying a house), I was thinking about what I could rewear, buy, or borrow to create three wedding guest looks, plus coordinating with various friends and family to figure out how we would get there and where we would stay. 

Wedding Guest Outfit #1 for a Labor Day Weekend Wedding in Cincinnati, Ohio

This wedding was the furthest of the three, and we went with the fun but time-and-scheduling intensive route of driving to Cincinnati and getting an Airbnb near the venue with friends. On Sunday, the wedding wasn’t until 5:30 and we got to meet the groom for lunch, which was so fun! We loved getting to check in with him before the wedding.

The wedding venue was in Mason, Ohio, at a beautiful carriage house with a huge patio and lawn. The ceremony was in a rustic space with a giant stone fireplace, cocktail hour was outside, and then we filed back into a ballroom in the carriage house for the reception. Since it was Labor Day Weekend (still technically summer) I wanted to wear something bright and playful. I settled on a J Crew hot pink cocktail dress with ruffled sleeves, a tiered skirt, and pom-pom accents. I bought the dress on Poshmark—I had seen it at J Crew a while back, but couldn’t justify buying it at the time since I didn’t have an occasion coming up to wear it. I was so lucky to find it later in my size! Since the dress was more casual, I accessorized with gold block-heel sandals and a gold clutch that I borrowed from my mom (thanks mom!). These heels are comfortable, but not comfortable enough for hours of dancing, so I brought a pair of flat gold sandals as well to wear during the reception. I had picked out some dangly earrings to go with this look originally, but I decided the dress was enough oomph without more statement pieces. 

Wedding Guest Outfit #2 for a Barn Wedding in Wolf Trap, Virginia

For this wedding, we were excited to be on home turf in northern Virginia! Since H was an attendant, we went to the rehearsal dinner as well as the wedding. I went to the rehearsal with H, which was good so I didn’t get totally lost trying to find the ceremony the next day, and then the rehearsal dinner was at Northside Social Falls Church, a trendy café and wine bar with a rooftop terrace. Choosing a rehearsal dinner outfit is tricky, since you want it to be a step up from an everyday look, but you don’t want to outdo whatever you’re wearing to the wedding. I wore a purple Madewell dress with a smocked bodice and ruffled straps, paired with sandals and a brown crossbody bag, for a fashion-forward outfit that wasn’t too dressy. 

The wedding was the next day at 5 in The Barns at Wolf Trap, a music venue/event space with a polished rustic vibe. Although the ceremony and reception were indoors, we all spilled outside during cocktail hour to enjoy the wonderful weather. For the wedding, I wore this dramatic full-length gingham dress. It was perfect for mid-September (I would have been SO HOT in that long skirt if I had worn it Labor Day weekend) and I love elevated gingham for a late-afternoon barn wedding. I paired it with a round rattan bag, which was easier to keep up with than a clutch, and neutral wedges, which were comfortable enough for dancing and the walk home from the after-party. I pulled this outfit together with items I already had in my closet—I also wore this dress to my cousin’s rehearsal dinner in Virginia Beach a while back and my birthday dinner in Georgetown.

Wedding Guest Outfit #3 for an Elegant Wedding in Richmond, Virginia

Our third wedding in September was a family wedding at the Commonwealth Club in Richmond, Virginia. We left early on Saturday (the last thing I wanted to do was miss my cousin’s wedding because of 95 traffic) and checked into our hotel with plenty of time. We were staying at the Quirk Hotel, which was only a few blocks away from the wedding venue. I had wanted to stay there for years, and it exceeded expectations—every space in the hotel was so aesthetically pleasing, and our whole room was decorated in light pink, from the walls down to the mini fridge. Somehow, H convinced me to leave our gorgeous hotel room so we could head to the wedding.

The weather was amazing (September weddings, amirite?) and the ceremony was on the Commonwealth Club’s beautiful patio with a view of historic downtown Richmond. The wedding had been originally scheduled for 2020 and postponed, so we were excited to see my cousin and his fiancée get married at last, and the ceremony was so sweet and personal. Everyone from my mom’s side of the family was there, and I loved getting to catch up with them during the cocktail hour and reception.

For the wedding, I wore a blue floral midi dress with shoulder ties and a full skirt that I got earlier this year. When I saw it, I knew it would be perfect for any of the weddings I was attending in September! I felt elegant but not overdressed, and even though the pattern feels a little more spring than fall, it’s so warm in Virginia in September that it still worked. I added neutral heels and a gold clutch (the same one that I borrowed from my mom) to finish the look. I have these shoes in white, and I liked the minimal silhouette so much that I got them in beige as well when I found them on Poshmark new in my size. They’re cute but not very comfortable, so I changed into my trusty gold sandals during the reception.

H and I were still wired after the reception, so we went to the rooftop bar at the Quirk Hotel for a nightcap. The rooftop had a great view of downtown and we loved the signature cocktails—try the Quirk Spritz if you go! The next morning, we had brunch at the lobby restaurant, which was also amazing, and checked out the art gallery. My aunt and uncle had invited us to their house for a casual post-wedding brunch, so we stopped on our way out of town for one last glimpse of the newlyweds.

As the final wedding weekend of September wrapped up, I felt so happy and grateful that we had gotten to see our family and friends. I might have felt a hint of relief that we would get back in routine at home, had we not had a backpacking trip planned for the following weekend!