Reese Witherspoon: Get the ‘Legally Blonde’ Star’s Most Stylish Draper James Looks Ahead of the Holiday Season

Reese Witherspoon has fast become a favorite on social media not just for her acting and producing credits, but the entrepreneur and smile icon has a style all her own — and one we are all incredibly smitten by. Between heading up her own media company, Hello Sunshine, and starring in the newly announced Legally Blonde 3 set to hit the big screen in 2022, Witherspoon’s clothing line Draper James has gone on to dress thousands of women across the country with its classic American style, steeped in Southern charm that is both feminine and pretty.

Revealing she started up Draper James to honor her “Southern heritage,” particularly the memory of her grandparents who were among her “greatest influences,” Witherspoon states on her website that they taught her everything about Southern style and the great American south. “From them I learned to dress and act like a lady, to take pride in my home, to reach out to help a neighbor, and to always invite everyone in for a visit,” she said before sharing how the name of her brand itself pays respects to the two: grandmother, Dorothea Draper and grandfather, William James Witherspoon.

With the holiday season about to commence as Thanksgiving nears just a month away, it’s time to get a head start on shopping for the cutest outfit this year — and Witherspoon is willing to help! Embodying the best of southern style and charm with grace, here’s how you can emulate the Big Little Lies and Little Fires Everywhere star’s best looks care of Draper James!

Loretta Shirtdress in Painterly Floral

Whether it’s Thanksgiving or Christmas get-togethers, this perfect fall dress is ideal for the holidays and priced perfectly at $135. Named after one of Witherspoon’s favorite country singers, this tiered midi with ruffles at the cuffs and a waist-cinching silhouette features a charming mix of painterly fall florals, culminating with a face-framing V-neckline in a contrasting print. Accentuated with side-seam pockets for functionality and a removable belt, the look is a sweet and flirty addition to your wardrobe. View more details at Draper James here. Complete the look with the classy and chic, Draper James Crystal Star Gold Mini Hoop Earrings for $58.

Fit & Flare Dress in Dahlia

True to size, this exquisite silk dress for $275 is accentuated with a beloved fall flower, featuring flattering lines and subtly sheer puff sleeves. Perfect for holiday parties, get-togethers and even date night, this bodice-lined, midi-length dress with a vibrant print mixing at the bib and flounce hem adds an eclectic touch to your wardrobe. Pair with your favorite white ankle boots or penny loafers for a casual look. View more details at Draper James here. Complete the look with a pair of Wire Hoop Earrings in gold for $38 and a cute, Straw Tote now on sale for $85.

Kacey Faux-Wrap Dress in Wispy Floral

Starring a harvest of reds, violets and navy, this perfect fall palette inspired by huckleberry, raspberry and boysenberry elevate this stylish look for a must-have this season. Currently retailing for $195, this wrap dress is an instant classic that can be paired up or down depending on the occasion. Cut from textural crinkle chiffon and adorned with painterly florals, this charming dress features feminine flutter sleeves and a waist-accentuating smocking at a flattering midi length. Feminine and clean, this exquisite dress is a must-have for the season! View more details at Draper James. Complete the look with its complementary fall accent, the Magnolia Double Drop Earrings for $48 in a lavender acetate.

Awning Stripe Loretta Shirtdress

Touted as one of Witherspoon’s “favorite dresses,” this transitional dress from summer to fall is a year-round classic thanks to its navy-and-white stylization. On sale for $102 — $33 off its original price — this midi dress blends the crisp style of cotton menswear shirts with elongated vertical stripes for super feminine details. Paired best with sneakers and loafers in warmer weather, or heels and booties for fall, this flowy tiered dress with a tie waist also features subtle ruffling details at the sleeves for a fun, flirty look. View more details at Draper James. Complete the look with the Crochet Raffia Tote, now on sale for $75, featuring leather trim, two interior pockets and one with zip closure.

June Dress in Marigold Floral

This new arrival for $250 is an instant classic, cut from luxe silk sateen and accentuated with pretty fall-ready florals. The exquisite dress, made with a cotton, rayon and silk blend, is ideal for date night or that special fall party. Featuring a romantic sweetheart neckline, floaty sleeves and side-seam pockets, the flattering lines and elegant midi-length elevate this dress as the season’s best must-have. Dress up with your favorite pair of heels or pearl earrings, or dress down casually with a jean jacket, sneakers and brown belt. View more details at Draper James.

Denim Field Jacket and Gingham Face Mask

For those looking to complete their look this season with the model jacket, Draper James has the cutest Denim Field Jacket for the stylish fashionista. Currently retailing for $150, this everywhere fall jacket features utilitarian patch pockets to carry essentials. Best of all, you can wear it as a cool alternative to the classic jean jacket for a more feminine look thanks to its removable belt for the most flattering fit and tailored structure. View more details at Draper James.

Finally, no look is complete this season without a face mask — and Witherspoon’s got the cutest collection of 2020’s most wanted (and necessary) accessory. Available in four colors and currently retailing for $12 as a final sale, these 100% cotton, one-size-fits-most features adjustable contoured nose wire and elastic earloops for a personalized fit. Best of all, they are machine washable and can be air-dried. View more details at Draper James.

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