Flats vs. Heels: When to Wear Each

For years, the heels versus flats war has waged on, and while fall 2011‘s offered a few ultimatums (read: both styles are popular), it’s only made the question of when to wear either that much more difficult to answer. Luckily, we’re happy to guide you, so with new shoes for autumn on the forefront, here’s when to wear heels “ and when not to.

What: Bell-bottom pants

Heels or flats: Heels

With the 70s aesthetic a must-do for autumn ’11, to prevent pants looking bulky or shapeless, you’ve got to embrace a chunky or a wedge heel style. From the runway (Roberto Cavalli) to the chain store (GAP, H&M), the bell-bottom/heel combo has prevented the post-grunge look of the late 1990s from coming back, as memories of tattered, stepped-on denim are combatted by a well-placed lace-up ankle boot or classic Mary-Jane. (After all, we didn’t say all aspects of the 90s were that great.)

Check out Aldo’s Munsch Chunky Heel Half-Platforms in Camel, $135. Available at Aldo.

What: The gentleman look

Heels or flats: Flats

While heels can be paired with a vintage-inspired cigarette pant or even pleated trousers and a classic, crisp button-up, to channel the gentlemen trend of the upcoming season, a lace-up oxford is a must-do. With designers like D&G showcasing their mix of masculine and feminine alongside patent, flat dress shoes, the flat has evolved from just a cute slip-on to a fashion staple, as the polished footwear of the 40s and 50s remind us why we keep romanticizing this one golden age.

Check out Free People’s Kane Heel Brogue in Black, $155.72. Available at freepeople.com.

What: Midi skirts

Heels or flats: Heels

Thanks to nearly every collection this season (from Gucci to Margaret Howell to Banana Republic), midi skirts are this autumn’s ultimate fashion bottom, with pencil cuts to A-line styles providing the perfect alternative to summer’s ankle dresses or cold-unfriendly mini skirts. Luckily, like the skirts themselves, their footwear counterparts are just as versatile, with lace-up ankle boots, knee high leather boots or even classic pumps working to channel whatever aesthetic you hope to embrace. (We’re looking at you, Bevery Hills 90210 fans.)

Check out Cole Haan’s Stephanie Air Chukka Lace-Up Boots in Officer Blue Suede, $328. Available at Cole Haan.

What: Skirts with socks

Heels or flats: Flats

True, heels with socks is by no means a faux pas (just look at the deluge of socks and chunky sandals this summer), but if you’re hoping to channel the recess vibe of back-to-school, you’ll want to stick with a lace up or sneaker (like Keds) to keep short skirts and ankle socks looking daytime appropriate. After all, it’s a fine line between channeling prep school and playing dress-up “ and Halloween’s over a month away.

Check out Browns’ Browns ID Leather Ballet Flats in Black, $128. Available at Browns Shoes. 

Tags: boots, fall 2011, fall 2011 fashion, Fall trends, fall trends of 2011, flats, heels, oxford lace-ups, what to wear in fall 2011

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