Shoshanna Lonstein Gruss was born and raised in Manhattan, studied history and art history at UCLA, and learned design and garment construction working at a lingerie factory. In 1998 she started her own label in New York, and the first collection arrived in stores that November. It was three dress shapes in three colors, and each one shipped with a purse and a matching bloomer, which is exactly the kind of detail that makes a brand feel personal. The dresses here keep that sense of play. The Eleanor Dress, the Gabrielle Dress and the Satin Column Dress are clean evening shapes, while the Perla Embellished One Shoulder Dress and the Raven Cap-Sleeve Floral Lace Gown go for more drama. Lace is a favorite across the group: the Elie Empire Lace Dress, the Tory Lace Mock Turtleneck Midi Dress and the Elyse Lace Ribbon Midi Dress each use it differently. For lunch or the office, the Cleo Knit & Faux Suede Midi Dress and the Aspen Mix Media Midi Dress feel more relaxed. For ideas on lace for a formal night, I wrote about lace or macrame for a formal dress.

Shoshanna built the label around flattering different body types, and especially petite curvy figures, so the fit is the thing to look for here. Wrap and tie-waist shapes such as the Harrison O-Ring Wrap Midi Dress, the Lily Sleeveless Wrap-Front Crepe Mini Dress and the Maggie Tie-Waist Rib Knit Mini Dress let you set the waist yourself. The Janice Buckle-Detailed Rib-Knit Fit & Flare Dress and the Cleo Combo Rib-Knit & Vegan Leather Midi Dress mix textures for cooler weather. The Mona Sequined Denim Off-the-Shoulder Dress and the Mae Denim Tie-Waist Mini Dress put denim in a more playful place. For formal nights, the Bolton Tulip-Sleeve Corded Lace Gown, the Montague Lace Mermaid Dress and the Carley Stretch-Crepe One-Shoulder Gown are the longest options, and the Brianna Velvet Dress and Serafina Metallic Flutter Sleeve Dress suit a party. What I would skip is wearing the Mermaid or Carrington One-Shoulder shapes to a seated dinner where you will be moving a lot, since the narrow skirt is built for standing and walking short distances. My notes on cocktail dress shapes cover how to choose between them.

Swim came later, in spring 2001, and it came with an idea. Shoshanna was the first to sell tops and bottoms as separates with lingerie-inspired sizing, which meant you could finally buy each half in the size that fit. The one-piece styles here include the Embellished One Shoulder Ruffle One Piece Swimsuit, the Lace Up One Piece Swimsuit, the High Neck Wave Texture One Piece Swimsuit and the Ring One Shoulder One Piece Swimsuit, plus the simpler Halter Strap Swimsuit. The Striped Short Sleeve Rash Guard & Bikini Bottoms is the sporty pairing, and the Sequin Jersey Triangle Bikini Top & Sequin Jersey Bikini Bottoms and Embellished Triangle Bikini Top & Bikini Bottoms are for the evening swim. Wear a one-piece with the high neck for a more covered look, or the lace-up with a wide sarong for the beach. For what to put on over any of them, cover-ups that do more work has plenty of ideas.

The last group is four shirtdresses with a clear pattern story. The Vesey floral-print stretch-cotton mini shirtdress and the Chatfield Striped Cotton Poplin Mini Shirtdress are the short ones, and the Laine Plaid Charmeuse Midi Shirtdress and the Barnet Ruched Stretch Cotton Midi Shirtdress are the longer options. Gruss is passionate about producing clothes locally in New York's Garment District, so I like to think of these as the practical side of the brand, meant for a real workday rather than a red carpet. The cotton ones are the easiest to wear again and again, and the charmeuse is the dressier of the four. Belt the poplin one and wear it with flat shoes, or leave the charmeuse one open over a slip for evening. A quick fit test for any shirtdress is to sit down and reach forward, because a good one never pulls across the back.

I would pick one of the lace dresses for a wedding, the Eleanor Dress for a dinner, and a one-piece swimsuit for the first warm weekend. The brand started with a purse and a bloomer in every box, and I still like that a Shoshanna dress feels thought through. For more dresses for a trip, I keep going back to a vacation dress guide, and for a fall invitation, a fall wedding guest dress edit pairs well.

For more in the same spirit, take a look at Oceanus Dresses and Swimwear and Frankies Bikinis Knitwear & Dresses.