It’s time for the Valentine’s edition of the Today show’s Style Me Something Good! Here a fun couple from Santa Rosa, CA, each tackle their style challenges to get transformed for a romantic date night!

KELLIE: SWEET STRIPES

For Kellie, lover of vintage fashion and proud owner or a 1973 MG Midget and 1963 Aristocrat Lil’ Loafer trailer, it’s a 50’s fit-and-flare silhouette from Modcloth in bold vertical stripes that will flatter any body type. Delicate jewelry from Kate Spade in rose gold add a touch of bling. Strappy heels by JCPenney gently elevate and are the first that Kellie says she’s worn in 30 years! “These are so so comfortable and don’t hurt!” she exclaims.

With her husband calling her, ‘super glamorous’ and with her love for the deep pockets in her dress as she twirled about our fitting, this striped number fit her personality perfectly.

Taken for a Spin Swing Dress, $95, modcloth.com

Brilliant Pavé Mini Huggers in rose gold, $48, katespade.com

Legacy Logo Spade Flower Mini Pendant, $68, katespade.com

Worthington Women’s Kasen Cone Heel Pumps in black, $41.25, jcpenney.com

Revlon One-Step Hair Dryer and Volumizer, $59.99, revlonhairtools.com

RON: CALIFORNIA COOL

Set aside his Cal Trans orange uniform for now, this sleek ensemble of cropped white pants topped with mock gray sweater and deep navy shirt jacket from H&M, provides the perfect warmth and style for Northern California living. Note the cropped style on the white pants which are the trend! He describes it as practical yet dressy and easy to wear. “All dressed up and nowhere to go!” he says.

A lace-up oxford shoe from JCPenney is part formal, yet part relaxed in the gray hue.

Relaxed Fit Shirt Jacket in dark navy, $34.99, hm.com

Merino Wool Sweater, $69.99, hm.com

Cropped Pants Regular fit in cream, $11.99, hm.com

Nunn Bush Barklay Lace Up Lace up Oxford Shoe, $54.99, jcpenney.com