How to Style a Pencil Skirt

One clothing item that has survived the test of time is the pencil skirt. This skirt style was designed by Christian Dior and introduced in his 1954 Autumn Winter Collection. It was a drastic deviation from shapeless WWII, and designed to give women back the “art of seduction.” Getting the perfect pencil skirt is one achievement, but knowing how to style a pencil skirt is quite another.

Most women that I know have an inherent desire to look their best, to add a dash (or huge dollop) of sexy to their wardrobe while still maintaining a respectable style. A pencil skirt is such an classic look- clean lines, form fitting without being gauche, and a veritable chameleon for multiple occasions.

 Tina, modeling a pencil skirt in Tokyo.

I recently met Tina Aiello, designer of a new collection of pencil skirts which comprise her brand Kakes & Beege. Tina is a former model, starting her career at 20 and traveling the world posing for numerous famous photographers and magazines, including Vogue. She definitely knew how to style a pencil skirt!

This photo was taken in New York where Tina lived and modeled during her career.

This particular photo was in Vogue and shot by Victor Skrebneski, who has photographed Cindy Crawford, Audrey Hepburn, and Diana Ross.

After years in the modeling industry, Tina settled in Chicago and pursued a career in art. The combination of working with high end clothing and producing her own works of art came together in the form of clothing sketches. It took 10 years for her dream of producing a line of clothing to come to fruition, but Kakes & Beege (her children’s nicknames) has officially launched with their first collection of pencil skirts.

I asked Tina why she choose this particular piece of clothing, and she raved about the versatility of a pencil skirt- you can wear it to work, play and everywhere in between. Dress it up with a silk blouse and heels, or dress it down with sneakers and a tshirt. Tina’s fit philosophy is comfort, ease and body skimming: not too tight or too lose, just complementing a woman’s curves.

Tina is absolutely stunning both outside and inside- she has had an incredible career, raised two children with her husband Frank, and is just as vibrant and interesting as her artwork (she painted this promo!).

I wanted to invoke Tina’s love of simple silhouettes and combine them with my unique taste when putting together looks with her gorgeous designs. Kakes & Beege skirts are currently available in three styles.

Gray/Blue Metallix Lurex Blend with Silver Metallic Leather Tape 

I styled this with the perfect white t-shirt (that I found after trying on dozens!). Add a sparkly pair of earrings and metallic heels to pull it together. Matching the metallic hem tape with your shoes just looks so chic. 

Black Wool with Faux Fur

This skirt strikes a balance betwen sexy and sophisticated. The wool skims curves without clinging and begs to be paired with a slinky camisole. Date night, holiday party, office work, running errands- I wear this EVERYWHERE. A red lip (Ruby Woo is a classic, it has been around but just won a best of beauty award at The Makeup Show). I paired this with the sexiest heels ever and a quilted gold chain bag and added a Bombay Taxi Boutique gold cuff.


Black Twill with Faux Leather Fringe

I had a blast styling this fun fall fringe option! I went a little cowgirl with a basic Levis denim button down and vintage cowboy boots that I found at Beatnix.



Kakes & Beege skirts are no longer available on their website, but you can find a similar styles on Etsy. I love supporting local small businesses, especially when they are borne from a long standing dream.

Cheers to feeling a little sexier by simply putting on a pencil skirt AND achieving your dreams!

How to Style a Pencil Skirt- All Dressed Up with Nothing to Drink