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May is always a wild ride—and this year, I’m right in the thick of it. Between graduations, team banquets, school events, and work that shows no signs of slowing down, we’re living in a full-on sprint. It’s the kind of month that demands outfits that look good but don’t require a second thought—which makes digging into our analytics even more fun.
I always love seeing what you’re loving most, and this month’s best sellers were a perfect reflection of how we’re all trying to dress: elevated but easy, polished without being overdone. It was a mix of fun prints, standout dresses, smart staples, and budget-friendly finds—and I’m so excited to keep leaning into this direction.
As things continue to grow, we’ve started making a small but important shift: you’ll see The Well Dressed Life stay focused on thoughtful, evergreen content—think seasonal wardrobes, outfit formulas, beauty routines, and style strategy—while quicker updates like sales, limited-time deals, and real-time finds are now being shared on Substack. It’s a flexible space and this content will be totally free for all subscribers, so it’s a great way to stay up to date without missing anything in between blog posts.
So if you’re curious about what made it into everyone’s carts—or just want to make sure you didn’t miss anything—here are the top-selling items from May.
May Reader Favorites
Faherty Sandbar Dress – Effortless Warm-Weather Style
This breezy dress was a fast favorite. With its flattering v-neck, adjustable waist ties, and soft, crinkled texture, it’s the kind of piece that feels like summer—easy, unfussy, and still pulled together.
The deep navy keeps it classic, while the flowy shape makes it ideal for everything from travel days to outdoor dinners.
Shop: Faherty Sandbar Dress, $198 | Sizes XS – XL
UNTUCKit Frida Shirt – Bold & Breezy Summer Staple
This sleeveless popover quickly became a standout. The vibrant jungle print adds a playful touch, while the linen-blend fabric keeps things cool and comfortable. It’s wrinkle-resistant, making it perfect for warm springtime afternoons. UNTUCKit
Pair it with shorts for a casual look or make it a dress with the matching skirt for an evening out. It’s that effortless piece you’ll reach for all season long.
Shop: UNTUCKit Linen Blend Frida Shirt, $79.50 | XS – XL
Longchamp Large Le Pliage Tote – Timeless and Travel-Ready
The bold pink is a fun, unexpected twist on a timeless favorite, adding a fresh pop of color to your everyday wardrobe.
Durable, lightweight, and folds flat for travel, it’s the ideal companion for everything from errands to summer trips. An easy yes, especially at this price.
Shop: Longchamp Large Le Pliage Tote, $155 now $119.97
Faherty Sunwashed Tee – The Perfect Everyday Basic
This tee has that perfectly broken-in feel right out of the package. It’s soft, lightweight, and drapes just right—without clinging or feeling too sheer.
A true wardrobe staple, it layers easily but looks great on its own with jeans or shorts. If you’re rebuilding your basics, start here.
Shop: Faherty Sunwashed Essential Tee, $58 | XS – XL
Faherty Sunwashed Fisherman Sweater – Laid-Back Coastal Vibes
A surprise best seller for May—and proof that an easy, lightweight sweater has a place in every summer wardrobe. This one’s soft and breathable, with a relaxed fit and a classic stripe that feels just nautical enough.
Throw it on over a tee for chilly mornings, pair it with shorts at the shore, or keep it in your bag for cool nights. It’s the kind of piece you’ll wear more than you think.
Shop: Faherty Sunwashed Fisherman Sweater, $198 | XXS – XXL
Tory Burch Ballet Loafer – Polished, Practical, and Worth It
These are one of those rare finds that feel just as good as they look. With buttery suede, a cushioned footbed, and a flexible sole, they’re incredibly comfortable right out of the box—no break-in time needed.
The neutral shade works with everything, and the subtle gold logo adds a hint of polish without being flashy. A true wear-with-anything shoe that’s worth the investment.
Shop: Tory Burch Ballet Loafer, $298
Boden Grace Linen Top – Colorful, Breezy, and Easy to Style
This top was a standout this month, thanks to its bold, cheerful print and effortlessly flattering shape. Made from breathable linen, it’s light enough for hot days but polished enough for casual office wear or dinner out.
It’s the kind of piece that instantly pulls an outfit together—just add white jeans or shorts and go.
Shop: Boden Grace Linen Top, $135 | Sizes 0 -22
J.Crew Factory Tiered Tank Dress – An Easy Pop of Color
This budget-friendly find was an instant hit. With its stretchy, fitted tank-style top and flowy tiered skirt, it’s one of those dresses you can wear on repeat all summer long.
The bright red-pink shade makes a statement, but the silhouette is simple and unfussy—perfect for everything from casual barbecues to beachside dinners.
Shop: J.Crew Factory Tiered Tank Dress , $64.50 | Sizes XS – 3X
J.Crew Factory Cotton Gauze Cover-Up – Simple, Chic, and Sun-Ready
This lightweight button-down cover-up has been a reader favorite for good reason. It’s breathable, soft, and easy to throw on over any suit—without adding bulk or heat.
The crisp white keeps it classic, and the longer length adds just the right amount of coverage. Perfect for pool days, beach trips, or grabbing lunch after the water.
Shop: J.Crew Factory Cotton Gauze Cover-Up, $54.50 | Sizes XS – 3X
Banana Republic Matte Silk Maxi Dress – Luxe, Light, and Statement-Making
This one made the best-seller list fast—and it’s not hard to see why. The silk crepe de chine feels weightless, and the open-back detail gives it a modern edge while staying elegant.
The warm tie-dye-inspired print is bold but wearable, perfect for summer weddings, vacations, or any moment you want to feel dressed up without trying too hard.
Shop: Banana Republic Matte Silk Open-Back Maxi Dress, $350 now $245 | Sizes 0 -20
That wraps up May’s best sellers—and I hope this roundup helps you spot a few new favorites. I always say the numbers don’t lie, and this month, they showed a community that’s leaning into easy, elevated pieces that actually work for your day-to-day life.
As our platform grows, I’ve been more intentional about where and how we share content. The Well Dressed Life will continue to focus on thoughtful, evergreen style—style how-tos, wardrobe guides, outfit formulas, beauty deep dives you can actually use, and the kind of advice that helps you get dressed with more ease and less second-guessing.
Over on Substack, I’m sharing more in-the-moment updates: quick sale finds, discount codes, one-off deals that don’t always make it to the blog, and spotlights on new and emerging brands worth knowing about. All of that is totally free and open to every subscriber. We also have a few exclusive posts each month just for paid members—more personal essays, deeper style strategy, and behind-the-scenes content.
You can join us here—it’s easy to subscribe, and I’d love to have you.
And if you picked up one of this month’s best sellers, let me know! I always want to hear what’s working for you.