The limit does not exist on the number of plaid shirts a gal can own! Reese Witherspoon wears this navy blue one tucked into a pair of clean straight leg jeans with cognac ankle boots - three of our favorite closet staples! And how awesome is her crossbody bag? Say goodbye to fussing with your purse and try a bag with external pockets like this one! A lot of these items are on major markdown, so jump on it while the holiday sales are white hot.

Just when we thought we couldn't be more obsessed with this season's leopard trend... Olivia Culpo one-ups them all with this plunging neck shirtdress. To die for, right?! This perfect match for less and some pointed-toe ankle boots like hers will turn heads at any and all occasions this winter - just don't forget a jacket! If you're worried about showing too much leg, some over-the-knee boots would be an instant stunner with this dress, too. Her belt bag is small but has dual use in holding the essentials while also giving some shape to the dress with a cinch at the waist. This double chain belt bag from Express is a spot-on spin-off! Since we want the dress to be the main attraction here, we love the simple touches of white nail polish, a demure lipstick, and simple silver rings.

Though she recently announced that she's hanging up her Victoria's Secret Angel wings, Rosie Huntington-Whitely will forever be one of our favorite model style icons! She is the queen of enviable style that doesn't scream for attention, yet they always grab our eye. This is one such look here with a classic A-line skirt, cropped long sleeve top, and white shoes. It's almost never a bad idea to throw in a fun bag to break up neutrals, and she achieves this with this shearling logo Fendi bucket bag. And in true model form, the dark oversized sunglasses are a must to complete this flirty yet chic outfit.

The former Disney star is now a streetstyle gal to keep an eye out for! Ashley Tisdale rocks a contrast collar dress underneath a fabulous single-breasted black coat. Maybe it's just the round sunnies, but this is looking a bit retro, don't you think? We found the PERFECT lookalike caged pointed-toe flats for a super reasonable sale price and tons of sizes available. We are convinced that these will be the best go-to holiday party shoes! The fuzzy handbag is an excellent example of a funky but super on-trend piece that spices up a monochrome look, and still keeps the class of this look overall!

Trendy pieces can always be hit or miss, and we're thinking this cape on Jessica Biel is one to consider! She wears it over a classic ivory and black fair isle sweater (a sure sign that Christmas is on the way!) and black washed skinny jeans and suede ankle boots. Jessica's sunglasses are from Privé Revaux, a super affordable line of trendy and timeless shades. Unfortunately, we can't say the same about her Jimmy Choo bag, which runs for $1,280. Love it, but we'll leave it and take a reasonable box bag from French Connection (bonus: it's on sale, down from $118). This is the perfect outfit for a gift shopping day with some girlfriends, Thanksgiving dinner at your aunt's house, winter date night...the possibilities are endless and sweater season is just getting started.