There’s a chill in the air, and your tennis sessions are no longer quite so sweaty! Fall officially arrives next week, and its crisp mornings, sunny days, and cool evenings mean one thing: it's layering season.
Here are 17 pieces to help you stay warm for everything the season brings, from tennis games to apple picking. We’ve found the very best lightweight jackets, sweaters, skirts with built-in leggings, sweatpants, water-resistant pieces, and more…
ON COURT
Ultra-stretch, full-zip hoodie with UV protection: $39.90. Smooth fabric designed for layering; the hood features a built-in “visor.” Available in 4 colors.
Sweat-wicking long-sleeve performance top: $88. 6 colors. Four-way stretch in an odor-reduction fabric.
Flattering pleated tennis skirt with built-in tights: $128. A Tennisette-reader-favorite skirt with leggings attached. 4 classic colors. Pair it with a matching cropped lightweight popover: $128. Available in 9 colors.
Here’s another “skegging” with no pleats: $89. Available in white or black. UV protection plus warmth!
Lightweight seersucker half-zip jacket in “sand”: $215. Wear it over a sweater on particularly chilly mornings or evenings!
Relaxed-fit cotton sweatshirt: $128. Crewneck, all cotton, 6 colors. Sizes from XXS to XXXL.
Water-resistant full-zip lightweight jacket: $119.99. With snappy white piping detail. Available in navy or basil.
Relaxed-fit cotton V-neck sweater: $148. Washable, available in 3 colors. Sizes XXS to XXXL.
Lightweight performance jogger: $110. Slim fit, side pockets, ultra-soft fabric, slightly cropped leg. 8 colors. Sizes from XXS to XXL.
OFF COURT
Adorable custom tennis cashmere sweater: $175-$215. Custom embroidered words or initials plus a tennis ball! 7 sweater colors to choose from, 35 thread colors.
Rugby-stripe cotton mini dress: $102 (on sale!). A preppy classic inspired by team jerseys in thick cotton. Available in 2 striped colorways.
Cozy camel wool heirloom squirrel cardigan: $168. Whipstitch detail, front pockets. Pre-order: available October 15.
Quilted tennis-ball heritage jacket: $275. A great layering piece with a classic preppy vibe! Patch pockets and a relaxed fit in a very fall-appropriate brown.
The waxed barn jacket: $325. A fall must-have! Water-repellent, waxed cotton, fully lined, with a corduroy collar. Available in 5 fun colors.
Crisp mornings and evenings call for a sharp, tailored wool blazer: $328. Herringbone pattern with suede details, relaxed fit, front patch pockets in 2 colors.
An elevated track pant with sporty side stripe: $128. Slouchy and comfortable: perfect for pulling on after a tennis game or watching the kids’ soccer from the sidelines! Elastic waist, side pockets. 2 colors.
Low-rise corduroy pants: $138 (plus 25% off everything in Madewell’s Insider Event!). Relaxed straight leg, 100% cotton, available in 3 lengths and 2 colors.










