As the weather cools, many are reaching for pieces that reflect an Oliver Twist inspired look. View any street style blog or fashionista’s Tumblr page and you’ll see that a preppy, hipsterish (aka “Prepster”) look has really become mainstream. Fitted blazers & vests, oxford shirts, loose skirts and lean cut trousers are mainstays again (stylized to fit personal tastes, of course). *Images via tumblr Campaigns featuring the look: Brooks Brothers J.Crew Alice + Olivia The go-to shoe with this look has always been flats, converse, oxfords, or pumps, however if you’re ready to try this trend this fall but don’t want to go with the usual suspects, think about investing in a pair of suede desert boots. Madewell Suede Sandstorm Boot, $178 Extremely versatile, you can still get the prepster look without looking like you’re headed to a Beatnik gathering. Many are fan of the original flat style first created by Nathan Clark (Clark’s), however for this year I recommend selecting a pair with a 1-3 inch heel in tan or light gray to keep the look feminine. Wear a few times to break them in; you can also shop vintage if you want a more lived-in look. SJP with skinnies, scarf, and a belted sweater. Rachel Bilson wears the trend with cropped shorts, white tank, and a blazer. Kors by Michael Kors Davina Ankle Boot, $250 J. Crew Suede Ankle Bootie, $250 Old Navy Suede Desert Wedge, $37 Opening Ceremony Chantal 5 Platform Suede Ankle Boot, $399 With this trend, remember to accessorize. Scarves, wooden bangles, gem broaches, and pearl necklaces pair well with these looks. Also try switching out the laces with fun colors like colbalt blue or purple. Do you own a pair? Do you plan on investing? Comment below and let us know how you feel about this trend. Ways to Wear: Slim jeans, checkered shirt, and a lightweight vest or cardigan. Add a small cuff to jeans and wear a pair of colorful slouchy socks. Pleated skirt, lace camisole, and a chambray shirt. Top with belt (keep the look lean) and wear alone or with tights. More Options: Boys & Girls Club | Cassie Rocks Obesity and Speed for Status Magazine Ask Kimmie | Polka Dots & Ruched Frocks