Famed British author Oscar Wilde once said, "One should either be a work of art, or wear a work of art," and only the most fortunate among us get both at once. It's safe to say Sydney Carlson fits firmly in that category.

Since the dawn of Instagram, Sydney as defined herself as one of the key tastemakers in the digital age. She stays ahead of almost every trend, has an excellent eye for vintage, all while styling the kind of looks that rivals the professionals. Honestly, if there's any wardrobe we want to scour? It's Sydney's.

With her birthday this month, it felt only right to do a full retrospective on some of Sydney's best looks over the past year. Whether she's headed to the islands or the Olympics, Sydney has never stuttered when it comes to turning out an outfit that turns heads, and we are always excited for what she's going to show up in next. 

Scroll through to see the very best of Sydney Carlson's collection — hopefully, you'll get inspired for your own. 

 

THE POLKA DOT COAT

Carolyn Bessette Kennedy was obsessed with statement-making outerwear, and it's clear that Sydney has taken cues from the 90s icon. Going bold with an eye-catching coat is never a bad idea, especially if the bag completes the look.

 

THE BELLY-BARING SET 

Oh, you didn't think a crop top could constitute evening-wear? THINK AGAIN. Sydney goes Hollywood at the GQ Man of the Year party in a sheer, floor-length skirt and sequin crop top — proving you can make anything formal with the right mindset. 

THE NAKED DRESS

Tis the season to take risks! Sydney proves that you might as well go sheer or go home in something that shoes off your assets. This look in particular gave huge mermaid energy, and honestly we'll remember it forever. 

THE COASTAL GRANDMA

Pairing a pearl-adorned floral knit top, denim skirt and ballet slippers for a day in the sun? More timeless than you would imagine. Wherever Sydney found this highly unique poncho-meets-blouse, we need the deets immediately.

 

THE FULL FLORAL

If this look doesn't live rent-free in your mind — where have you been? Sydney rarely shies away from color, as evidenced by these capris and maybe the greatest belt of all time. If you're looking to recreate this outfit, the first stop has to be Ebay, as it is definitely comprised of thrifted finds. 

 

THE DENIM-ON-DENIM

Even though jeans never go out of style, you won't find Sydney doing any old denim. Elevating a jean jacket with fur cuffs, this is the Canadian tuxedo done differently (basically, super cute). 

 

THE VERSACE

ICYMI: over the holiday season Sydney wore a snow white, rhinestone-adorned, ruched Versace gown to the W Mag party. While there are very few full-length photos, it is etched on the memories of most as one of her most iconic outfits of all time. 

 

THE RALPH LAUREN LAYERS

While attending the Winter Olympics in Milan, Sydney layered up in a few Ralph Lauren classics. It was giving 1980s East Coast old money with crisply-tailored trousers, luxe outerwear and of course, Team USA memorabilia. 

 

THE EXOTIC BIRD

If you think all-black is boring, let this look prove you very wrong. A pencil skirt, bolero and bra is the new Hot Girl blueprint for 2026 — you heard it here first. 

 

THE SATIN SENSATION 

A square neckline and shoestring straps always signal minimalist chic, but mint green satin definitely takes the silhouette to the next level. This has to be one of the best dresses to ever appear on Earth, period — from the seams, guessing Vintage Dolce & Gabbana? — and with silver stilettos, well, it's all just too perfect.