The Only 4 Outfit Formulas You Need for Summer's Biggest Events

No stress this social season.

Sarah Chiwaya styling a black linen dress with boat shoes
(Image credit: Sarah Chiwaya)

Pool parties. Boat days. Outdoor brunches. With summer comes a whole slew of fun special occasions, but sometimes a packed social calendar can lead to wardrobe stress. My summer schedule really kicked into high gear this past week. I needed to put together looks for wildly varying venues, vibes, and forecasts.

Read on for summer outfit ideas for everything from late-night swims and sunset strolls to beachside weddings and galas.

Rooftop Pool Party: A Sleek Swimsuit and Baggy Shorts

Sarah Chiwaya styling Bermuda shorts and a swimsuit for a special summer occasion

(Image credit: Sarah Chiwaya)

It is no secret that I am a big fan of resortwear, but not all pool parties call for tropical attire. For a rooftop swim in the city, I wanted an outfit that made just as much sense on the sidewalk as it did poolside.

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I have a massive swimwear collection (I am a triple water sign, after all!). So, I had a lot of options when it came to choosing my first layer, but this sleek one-piece from TA3 was too good to pass up. Like the viral swim brand's best-sellers, this suit has built-in shapewear and an adjustable, waist-cinching corset back. Even without tightening the laces, it creates a great silhouette, but once pulled taut, it instantly shapes the waist.

I love this because it is super easy to switch between a more relaxed fit and full-on bombshell mode. I generally find TA3 Swim to be true to size, and this one was no exception. My only note about this style is that it is not easy to get on on the first wear (I needed to enlist my husband for assistance!), but once it's on, it's actually very comfortable.

Sarah Chiwaya styling Bermuda shorts and a swimsuit for a special summer occasion

(Image credit: Sarah Chiwaya)

For the party, I made the swimsuit an outfit with my favorite pair of one of summer’s biggest trends: Baggy longline denim shorts. This specific pair has been in heavy rotation since I got them a couple of months ago. The fit is spot-on and true to size. It's also the best cut of all the denim Bermuda shorts I’ve tried lately (all the other ones I’ve tried were clearly not designed for plus-size figures).

Accessorized with my go-to pair of heeled flip-flops and tortoiseshell sunglasses, I felt stylish enough for the industry networking portion of the Swim + Resort Day event. Then, I had a seamless transition when I was ready to hop in the pool.

Brunch at a Friend's Place: A Flowy Maxi Dress

Sarah Chiwaya styling a flowy summer special occasion dress

(Image credit: Sarah Chiwaya)

For a day of great conversation and homemade shakshouka at a friend’s house, I wanted to wear something equal parts comfortable and cute, so I went with a billowy maxi dress. This category is unmatched for feeling like pajamas while still looking considered, and is especially lovely for hot summer days.

I love the blue and white floral print on this one from Aveology, a boho-focused label from plus-size fashion stalwart Avenue. It fit perfectly through the bust (a rarity!), and is blessedly regular-bra-friendly (something that cannot be taken for granted when so many summer dresses require strapless numbers). The skirt had enough space to move with me as we went from brunch to chatting on the couch for hours. Plus, the soft viscose fabric never felt stifling in the heat.

The style details are so fun, too. From the contrast print border to the full-on bell sleeves, giving this a deliciously vintage vibe. The dress was doing all the work, so I could keep the accessories minimal: Just a pair of gold huggies and a small bangle.

Since printed maxis can work for so many summer occasions, my collection is never complete.

Yacht Day Watching the Sailing Grand Prix: A Lightweight Linen Dress

Sarah Chiwaya styling a black linen dress with boat shoes

(Image credit: Sarah Chiwaya)

Always on board for new experiences, I was beyond excited to watch the US Sailing Grand Prix from a gorgeous sailing yacht in the New York harbor. I’d never been to a sailing race before, so I had no idea what to expect. It was thrilling, with the sleek sailboats seemingly floating above the water as they sped through the curves of the course, and cheering for the U.S. team brought the electric energy of the race to our boat. If you ever get a chance to watch a SailGP race, from land or sea, I highly recommend it!

For my outfit, I needed something equally breathable and stylish. Translation: Linen. This A-line dress from designer Cynthia Vincent’s plus size label Baacal was just the thing. The shirt dress silhouette felt like the perfect mix of casual and composed, especially when the fuller skirt added a little drama.

One extra perk: Its midi length stretched long enough, so I wasn’t in danger of sea winds whooshing my skirt. Much like the TA3 swimsuit, its lace-up back gave it a cinched waist that is usually nigh-impossible to achieve as a curvy girl in a shirt dress.

Sarah Chiwaya styling a black linen dress with boat shoes

(Image credit: Sarah Chiwaya)

I paired it with my new, freaky shoe obsession: Boat shoe mules. Boat shoes as a whole have been rising in popularity over the last few years. But this hybrid silhouette from the recent Sperry x Abercrombie collab is the first pair that has me intrigued.

It functions just as well as original boat shoes (unsurprising, since Sperry originated the style), but with an interesting, delightfully odd twist. It earned me major props with the yachties too: They said “Boat shoes! You know ball,” as they helped me disembark the tender. I finished the look with my Longchamp Le Roseau bag (worn as a bucket) and a beloved pair of square Versace sunnies. I felt cool (literally and figuratively) all afternoon.

Pink Carpet Gala: A Statement Cape Gown

I’ve been married for years now, but I still have a deep passion for bridal dressing, especially when it comes to advocating for better options for plus-size brides. (My own wedding dress shopping experience was so bad that it led me to starting my own body-positive blog!) That said, I was delighted to get an invitation to this year’s The Knot Gala. It is an experiential showcase of the best of the best when it comes to wedding vendors (basically a wedding without the marriage part). I knew I had to come decked out in my wedding guest best.

Sarah Chiwaya styled a cape dress for a special summer occasion

(Image credit: Sarah Chiwaya)

Cape-sleeve dresses have been having a real moment lately when it comes to formalwear trends. It felt like the perfect time to pull out this sleek cape detail dress from plus size favorite Eloquii. The form-fitting silhouette had serious sexy bombshell vibes, but the high neckline and elongated sheer sleeves kept it from being too-too much for such a fancy event. Accessorized with my beloved metallic leopard Alexis Bittar clutch and a simple heel, I felt amazing and got a ton of compliments on my look.

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Sarah Chiwaya
Contributing Editor

Sarah Chiwaya is a plus-size fashion expert, size inclusion advocate, editor, brand consultant, and style influencer.