Ask a Stylist: How to Make Shorts and Flats Look Chic


Q:I’m moving to a new city where walking is the preferred method of transportation. I live in heels but I don’t want to walk a mile in them. There is also the summer heat to take into consideration. So my question is this, how do I pair shorts with flats without looking frumpy?

A: Great question. When the temperature rises the thought of slipping on a pair of jeans and heels makes me absolutely crazy. It’s simply not going to happen. I’ve actually amassed quite a collection of cute shorts and flats that are far from frumpy. The secret is in the combination. Let me show you the way …

Combination #1: Short-shorts and sandals

When wearing super-short shorts you want to show as much leg as possible to give the illusion of mile long legs. The best way to do this is with strappy flat sandals.

Rag & Bone shorts // Rag & Bone sandals

Combination #2: High-waist shorts and wedges

Okay, so wedges aren’t technically flats but they are comfortable and certainly easy to walk in – so there you go. Wear them with high-waisted shorts for a retro-inspired look.

Tucker shorts // Stella McCartney wedges

Combination #3: Tailored shorts and smoking slippers

A smoking slipper is a great alternative to a boring pair of flats. I love pairing them with a chic pair of tailored shorts for a dressier look.

Valentino twill shorts // Christian Louboutin slippers

Combination #4: Loose fitting shorts with ballet flats

A loose fitting pair of shorts is great for a girl with fuller thighs because it gives the illusion of having slimmer legs (we love that). Style this girly silhouette with a cute pair of ballet flats for a extra-cute vibe.

Moschino ruffled shorts // Lanvin yellow ballet flats

Lauren Messiah, is a Los Angeles based stylist and the creator of, a blog about designer deals, the hottest trends, and Lauren’s life as a fashion stylist.Lauren styles some of Hollywood’s most successful women in entertainment, celebrities, fashion editorials, and national ad campaigns. Lauren has been featured in Marie Claire, Vogue Italia, Grazia, WWD, OK! Magazine and Health Magazine.