First dates are stressful enough, add the dreaded question, “What am I going to wear!?” and you’re probably feeling a little overwhelmed. When it comes to your wardrobe selection, rest easy. Here are a few tips from a full-time fashionista.

(credit: Diane von Furstenberg for Bloomingdales)

Date #1, Night On The Town

900 North Michigan Avenue
Chicago, IL 60611-1515
(312) 255-0079
Sun 11am–7pm / Mon–Sat 10am–8pm

(credit: Intermix)

LBD, LBD, LBD. This one’s a no brainer and my go-to. It’s classic and requires little to no planning. I’m going to go ahead and assume you have one in your closet. Pair it up with jewels and a great pair of shoes and you’re good to go. My favorite LBD of the moment is Diane Von Furstenburg’s Helen Cap Sleeve Dress $365, available at Bloomingdales. Its cap sleeves give it a feminine look, while the v-cut back lets you show off a little skin. Plus, her dresses look great on just about every body shape.

If you’re looking for something a little more colorful, try a bold color or patterned dress. My personal favorite this season is Missoni’s Guenda Off-The-Shoulder Shift Dress, $1210, available exclusively at Intermix. Totally worth the splurge. It’s shimmery print has shades of copper, hot pink, ruby red, bright blue, sky blue, lilac, pale pink, taupe and black.

(credit: Banana Republic)

Date #2, Casual Coffee

If it’s more of a casual date (i.e. going to coffee, movie, etc.), dark denim skinny jeans and a cute top will work just fine. Pick a color that looks great and makes your eyes pop. For skinny jeans head to Banana Republic, their dark wash and light weight material is perfect for Chicago’s windy summer nights, $89.50.

Another option, fun and flirty floral dresses. They are always in style and very feminine. Try Urban Outfitters‘ ‘Sparkle and Fade Dancer Dress’ in the floral print, $49, paired with a brown belt and sandals.

(credit: Micheal Kors for Nordstrom)

The Perfect Shoe


520 N Michigan Ave
Chicago, IL 60611 

(312) 379-4300
Mon-Sat 10am-8pm. Sun 11am-6pm

Keep it simple ladies. Leave the man-repelling shoes at home (ahem… gladiator sandals). You’re trying to impress your date, not other females. Also, go for a reasonable height with the heel. No need to be Andre the Giant standing next to your date (Please Note: this does not apply to anyone under 5’2”). You should be comfortable and able to walk. My pick: Michael by Michael Kors ‘Flex’ peep toe pump, $97.95, available at Nordstrom. They are just the right height 3” with a ½” platform, and have a padded foot bed for comfortable wear.


Under no circumstances should you wear the following: drop crotch utility pants, harem pants, boyfriend jeans, fishnet stockings, any jewelry or shoes that look like they could double for weapons of mass destruction, or the aforementioned gladiator sandals.

What are your favorite first date outfits? Leave your comments below, we’d love to hear from you.

Samantha McCarthy is a freelance writer and editor in downtown Chicago. She wears many hats (and owns one too many pairs of shoes), with one of them always being in-the-know of the fashion industry.