I first picked up on the flannel shirt trend back in May when I noticed Lindsay Lohan sporting the look.  I didn't get the chance to show off the flannels I bought through the hot summer, so I'm happy that this trend is hanging on for fall 2008.  Celebrities like Mary-Kate Olsen have been seen playing with this look in all sorts of ways, and it's one you can adapt for yourself too.

Miley Cyrus keeps it comfy in an untucked flannel, cuffed shorts and gladiator flats.  If you're hesitant to wear the large shirt in the typical 'grunge' shades, take a cue from Lauren Conrad -- She picks a fresher hue and shows some skin to keep it girly.  Having the shirt tucked in emphasizes her waist.

I don't care for the jacket, but I love the way Lindsay Lohan works the flannel shirt with the boots.  A fashionable boot really separates the flannel top from its lumberjack roots.  Mary-Kate Olsen does a boot as well, working the oversized shirt over a pair of dark tights.  The slightly grunge look meshes well with the goth-inspired fashions forecasted for fall.  Work the ensemble with a large 'it' bag, or pick up one of the oversized clutches that are popping up this season.

Tips for making Plaid & Flannel Shirts Work for You:

• Makeup that face.  Try out dramatic eyes or a bold lip like MK above.  If you choose to go natural, at the very least layer on some mascara or wear your lips super glossy to offset the grunginess of the shirt.
• Emphasize your legs.  Shorts, a mini, or leggings are an excellent way to show off your shape.  If you wear jeans, go with your skinniest skinnies.  Too much bulk on your legs will make your whole body appear sloppy.  Consider how your silhouette will look.
• Try a belt.  A row of studs slung around the shirt at your hips will give you more shape and a unique edge.
• Roll up your sleeves.  Show off your wrists and forearms, which you can stack with dainty bracelets or clunky bangles.
• Work it as a frock.  A super long shirt will make a great dress for nights out -- just be sure to wear leggings or full-coverage booty shorts underneath.
• When in doubt, wear heels.  Lindsay Lohan has been seen out in an oversized flannel button-up, mini skirt and pumps looking fierce.
• Accessorize!  This is the perfect time to play with fall necklace trends or layer on funky sunnies for the rest of the sunny season.

Follow-up Reading:

Suze posted about the plaid/flannel trend popping up in D&G.  Stylegirlblog has this post comparing hipsters to lesbian trendsetters, while Lovelier Fashion has posted my favorite guide/inspiration to the flannel trend.  See also my personal experience thrifting for a flannel.

photos from:
People.com
Team Sugar