Winter 2026 ◆ Lookbook
The Court Society

THE
INDOOR
SEASON

Four looks for the stretch when play moves inside and the walk from the car is the coldest part of the day. Everything in this book arrived in the last few months, and most of it comes in small runs.

Four looks ◆ New this season ◆ Small houses ◆ Stark County, Ohio

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A midnight navy V-neck tennis sweater with white striped trim, from the Winter 2026 lookbook at The Court Society
Contents

FOUR LOOKS,
THREE PIECES EACH

Each look is built around one piece worth keeping for years, with two that earn their place beside it. We've put the price of the whole look under each one so you can see what you're deciding about.

  1. 01
    Midnight, with stripes
  2. 02
    Wine, and white over it
  3. 03
    Pink on a gray day
  4. 04
    Green, and green
Lucky In Love Preppy Court pleated tennis skirt in white with navy stripe trim, front view on model
Look one

MIDNIGHT,
WITH STRIPES

The Victory sweater came in at the end of October and it's the piece we'd put on first. It's midnight navy with a white striped V at the neck and the same stripe at the cuff and hem, cropped just enough to sit over a skirt. The white pleated skirt carries that navy line again at its hem, and the quilted tote is the one thing here that's openly about winter rather than tennis.

The look together $294

Add each piece in your size.

Lucky In Love Next Level tennis dress in wine, sleeveless with a sheer pleated mesh skirt, front view
Look two

WINE, AND
WHITE OVER IT

Wine is the color we kept coming back to this season. The dress has a mesh pleated skirt that moves the way the lighter ones do, in a deeper register, and the white throw-over goes over it without flattening the color. Its sleeves are cut with sheer panels, so it layers without adding much. The beaded clutch is a tennis court, players and all.

The look together $314

Add each piece in your size.

Runway Athletics fitted knit tennis sweater in pink with white stripe trim and a crossed racquet heart emblem, worn courtside
Look three

PINK ON
A GRAY DAY

A soft pink knit with white striped cuffs and a pair of crossed racquets at the chest, which is about as much cheer as a February morning asks for. The black wrap skirt keeps it from going sweet, and it has a real pocket with a snap, which almost nothing in this category does. The beaded clutch picks the pink back up.

The look together $300

Add each piece in your size.

Pink Pineapple green & pink pickleball sweater — women's pickleball apparel at The Court Society boutique
Look four

GREEN,
AND GREEN

The Pink Pineapple sweater is cotton, green with pink paddles knitted across the chest, and it's the piece in this book most likely to be worn somewhere with no court nearby. The Level Up dress is a deeper forest with a striped band at the waist, so the two greens sit together rather than argue. The cream clutch spells LOVE with a tennis ball and two gold racquets.

The look together $334

Add each piece in your size.

The shop

EVERYTHING HERE
IS IN THE SHOP NOW

We buy these in small runs from small houses, so sizes go and don't always come back. If you want something you see here and your size is gone, write to us and we'll tell you honestly whether it's coming again.

Shop the winter lookbook See what's new

The Court Society ◆ Stark County, Ohio