Dear FO Personal Stylist: From Office to Date Night

I have recently started dating a very nice guy and we have been going on dates several times a week. My challenge is that during the weekdays I find it extremely taxing to rush out of work to go home and get ready for our dates. However, my work clothes are so boring that if I wear them to my dates I feel totally unattractive and therefore lack the confidence I need during my dates.

I was hoping you can give me some advice on ways to transition my work attire to date attire without a complete shower and change of clothes.

Thanks,

Tina M., Chicago, IL

Dear Tina,

Assembling an outfit for a date or for the office alone can be a chore, so it’s no surprise that finding an ensemble that satisfies both scenarios is especially daunting. Even outside of the date/office continuum, most of us want to have pieces that are versatile enough for various situations or levels of formality.

There are some easy quick tips (think the 80s movie librarian pulling off her glasses and shaking out her ponytail to suddenly become the dream girl). A fitted blazer or grandpa cardigan can make your after business hours outfit more work-appropriate; likewise, date night trinkets can be stashed in your purse during the day and added later to liven up your work gear.

I’ve put together three possible office-to-date-night ensembles for you. As always, they are ultimately meant to provide some inspiration to incorporate into your pre-existing wardrobe.

Potential Outfit #1

Outfit #1 is for those who want absolutely no wardrobe transition from work to play. The neckline and hem on the dress are both work-appropriate, but the ruffles lend it a flirty appeal. Similarly, the closed toe heels have side cutouts to prevent them from being dowdy. The cardigan can simply be removed once it comes to date time. I would add a favorite belt, buckled over both the cardigan and dress, as a finishing touch to tie the ensemble together.

The Items

• Express’ Sleeveless Ruffle Front Dress, $69.50
• Banana Republic’s 3/4-Sleeve Open Cardigan, $24.99 (originally $59)
• Sam Edelman’s Fleur Vintage Dress Shoes, $116.22 (originally $138.95)
• Jane Diaz’s Pearl Earrings, $132
• Blu Bijoux’s Gold Bamboo Bangle Set, $15

Potential Outfit #2

Outfit #2 is a good example of the sexy librarian look. A fitted knee-length pencil skirt is paired with a scarf neck top (made less risque for work by adding a lightweight cami underneath). A statement ring and patterned heels, if both kept neutral enough, add business-appropriate personality to the look.

The Items

• Vivienne Westwood Anglomania’s Scarf-Tie Jersey Top , $140
• Corey Lynn Calter’s Built Up Waist Skirt, $90.50 (originally $181)
• Nine West’s Rocha Pumps in Snake, $59.99 (originally $79)
• Michael Stars’ Long Cami, $21 (originally $30)
• Jamie Joseph’s Drusy Ring with Diamond, $616

Potential Outfit #3

Outfit #3 is definitely the most happy hour oriented of the lot, and probably not an option for a super corporate environment. The key here is adding leggings so that the somewhat short dress functions more as a long tunic. I am a big fan of YFB leggings, as they are more like pants than tights (yet not bulky), but any heavier weight leggings should do. Come 5 PM, you can ditch the bottoms and add your layered necklace.

The Items

• Jean Paul Gaultier’s Striped Bubble Dress, $185 (originally $327)
• Larsen Gray’s Mini Trench, $183 (originally $305)
• botkier’s Carrie Ankle Boots, $259 (originally $594.95)
• Young, Fabulous, & Broke’s Tuxedo Leggings, $109
• Dereon’s Multi Chain Pearl Necklace, $38
• Amrita Singh’s Montauk Earrings, $38 (originally $50)

Have a fashion emergency, or just looking for a helpful hint or two? Email Fashion Orbit’s Personal Stylist!