From bold, shock-it-to-me prints to subtle newsboy caps, each of these pieces has one thing in common: it goes beyond standard seasonal transition fashion to fully refresh your look for spring.
20s: Romantic Pencil Dress
Carissima Sheath, Byron Lars ($258). Anthropologie, 111 E. Chicago Ave., 312-255-1848
Romantic and feminine—two defining traits of 1920s style. Add some romance to your own closet with the lace and appliquéd flower details on this perfect pencil silhouette.
30s: Tea-Length Dress
Belted Sleeveless V-Neck Full Pleated Sun Dress With Mesh Inserts, Donna Karan ($3,295). donnakaran.com
Tea-length dresses were favored by every woman in the 30s. Fast forward to 2015, and the style is still sophisticated and polished. To channel your inner lady, look no further than this brushstroke design and timeless length, updated with modern details like mesh inserts and a low V-neckline
40s: Newsboy Cap
Hans HT Grey Check Cap, Wigens ($128). Haberdash, 611 N. State St., 312-646-7870
Nothing looks more gentlemanly than a sharp wool newsboy cap. Made with century-old hand-crafting skills, it’s expertly made to ensure it'll last for the next seven decades.
50s: Girly Dress
Polka Dot Carnation Ruched Poplin Dress, Dolce & Gabbana ($2,495). 68 E. Oak St., 312-255-0630
Add some brightness to your wardrobe this season with this ultra-flattering dress from Dolce & Gabbana. The mix of polka dots and pops of red carnations show you're ready for the season, and all the events that come with it.
60s: Tailored Vest
Tailored Vest, Nickel ($290). BOGA, 133 N. Jefferson St., 312-801-8662
With Mad Men gearing up for its final few episodes, there's no better time to welcome a little bit of style inspiration from Don Draper. The easiest way is with a tailored vest, which looks just as good worn under a blazer or on its own.
70s: Flowy Skirt-and-Top
Ray of Light Set, Free People ($228). 1464 N. Milwaukee Ave., 773-227-4871
Bring back the era of free love with a crop top and maxi skirt combo. The 70s details come through with flared sleeves and embroidered details along the waistband.
80s: Bright Shift Dress
Clyde A-Line Shift Dress, Alice + Olivia ($298). 919 N. Michigan Ave., 312-273-1254
Electric colors and playful designs make this shift dress reminiscent of the 80s and a great new statement piece for 2015. Whether you want to take it a step further and ditch the flat iron for a crimper, it's up to you.
90s: Flannel Shirt
Textured Cotton Shirt in Orange Plaid J.Crew($88). 900 N. Michigan Ave., 312-751-2739
The Kurt Cobain-era defined by grunge style looks lightyears better when it's updated in a lightweight cotton material. Paired with a simple skirt, grunge meets girly in the best possible way.
00s: A Cropped Top
Joan Floral Cropped Top, A.L.C. ($325). Saks Fifth Avenue, 700 N. Michigan Ave., 312-944-6500
Since there's no use competing with the crop-baring stars of the early 2000s, lean on this bold floral top to embrace the trend of the decade. The slightly cropped fit adds to its versatility and proves to be a piece you can pull off through spring and into the summer.