Jessica Simpson Elevates Her Sweatpants & Cropped Hoodie in 5-Inch Plaid Booties

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Jessica Simpson showed an effortless way to pair your favorite heels with this year’s growing athleisure trend.

The “Dukes of Hazzard” alumna previewed pieces from her eponymous label this week in a matching cropped sweatshirt and sweatpants set. As shared on her Instagram Stories last night, the Essential Crop Hoodie comes with a $60 price tag and the Tight Jogger retails for $60 as well at JessicaSimpson.com.

jessica simpson, shoes, heels, plaid boots, sweatpants, sweatshirt, crop top
Jessica Simpson poses in pieces from her own label with plaid platform boots, Oct. 8.
CREDIT: Courtesy of Jessica Simpson/Instagram

While a sweatsuit typically gets matched so slippers or sneakers, Simpson proved that you can dress up any ensemble with the right pair of shoes. Her choice for the day? Her brand’s Irrena platform boot. The updated style features a fall-ready plaid flannel print with faux fur lining and Velcro closures. Set with a 2-inch lug-sole platform lift, the style comes complete with a contrasting 5-inch block heel.

You can find the online exclusive style at the brand’s website for $169.

jessica simpson, brand, label, Irrena, boots, plaid
Jessica Simpson Irrena boots.
CREDIT: Courtesy of Jessica Simpson

Throughout September and now into October, the “Employee of the Month” actress continued to show off new silhouettes from her own apparel and footwear label including the Irella floral boot. Similar to the Irrena, the design takes inspiration from lace-up combat boots with its utilitarian base, transforming the style with textured faux leather uppers and nail-head studs. Also measuring 5-inches in height,  the brand’s Irella boots retail for $170 and can be found at Amazon.com.

Known for her own style, Simpson launched her shoe line in 2005 in partnership with the late Vince Camuto. The Jessica Simpson Collection is currently owned by Sequential Brands Group, and it offers a range of affordable styles, including shoes as well as clothing and accessories for women and children. Simpson has additionally won big at FN’s annual Achievement Awards, taking home Launch of the Year in 2005.

When she’s not clad in footwear from her eponymous brand, Simpson can often be found in soaring styles from the likes of Saint Laurent, Jimmy Choo and Stuart Weitzman. The mom of three has also selected in recent months selected multiple pairs of snake-print knee-high boots from Villa Rogue, as well as Gucci combat boots and Fendi sandals.

As fall settles in, make sure you have all the flannel and plaid your closet needs with these next footwear styles inspired by Jessica Simpson’s chic boots.

plaid boots, flannel, tartan, checkered, fall, dr martens, doc martens
CREDIT: Courtesy of Dr. Martens

To Buy: Dr. Martens 1460 McMarten Tartan Boots, $80 (was $160).

sorel, plaid boots, flannel, tartan, checkered, fall
CREDIT: Courtesy of

To Buy: Sorel Lexie Boots, $170.

plaid boots, flannel, tartan, checkered, fall, penny loves kenny, dsw
CREDIT: Courtesy of

To Buy: Penny Loves Kenny Tuck Boots, $70.

Flip through the gallery to discover more of Jessica Simpson’s best footwear moments over the years.

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