Dresses for Every Season and Every Occasion

We all know that feeling: You’ve got a vacation, friend’s wedding, or business conference coming up (or maybe one of each), and you’re standing in front of your closet with no idea what to wear. Options are strewn across the bed, but nothing feels or fits quite right and the clock is ticking. What ever happened to fashion feeling fun, instead of feeling like another torturous chore on the to-do list?

Don’t worry, we’ve got you. Whether you’re packing for a family vacation, brunching with friends, heading to the after-work mixer, or stepping out for a date night, when you need dresses for events, travel, holidays, and more, finding the right outfit can be easy when you’ve got wardrobe staples that combine versatility, comfort, and timelessly chic appeal. We put together this style guide to take you from stressed to effortlessly dressed no matter the occasion.

Daytime Outings

From brunch with friends to an afternoon at the winery, daytime dresses are all about casual, comfort, and color. We love a dress that’s just as vibrant as the day. Unique prints are natural conversation starters, like our fun Koi Pond or Foxy patterns in our knee-length Megan fit. We also love a geometric or an abstract floral, like Groovy Gal. 

Nighttime Fun

Date nights, milestone birthdays, after-hour mixers, and any other evening event that doesn’t require formalwear should be all about eye-catching patterns and palettes, festive touches, and cuts that bring out your most confident self. A solid red always stuns for a date night, while the little black dress provides the ultimate in versatility; add Silver Foil for a festive touch. And if your celebration calls for a little sparkle, this Cecelia fit turns heads.

Vacation Planning

Are you an over-packer, or do you often find yourself wishing you had more options to wear on vacation? You can prevent either challenge by bringing versatile day-to-night dresses that allow you to look and feel your best after a day of museum hopping, souvenir shopping, or sipping seaside cocktails, followed by a romantic dinner for two or evening of family fun. This magenta Art Nouveau design combines sophistication and comfort (and has pockets). The fiery Autumn Sunset’s Connie fit features an elegant cowl neck. The mauve Mesa Maize offers a fun geo print in warm hues.

Reunions and Weddings

Where there’s a group party, there’s bound to be food and music, and the last thing you’ll want to worry about is whether your outfit stays sophisticated and comfortable after hours of hugs, dancing, dining, and maybe even sitting down at some point. As a wedding guest, florals are always in, like the Mumbelievable, and a whimsical paisley is on point, especially in velvet, like this Emily fit. Other intimate gatherings call for timeless sophistication like Elegant Blooms or our Velvet Damask.

Even small changes — swapping your belt, adding a wrap, or trading boots for pumps — can take your outfit from relaxed to refined.

If you ever find yourself in a rut agonizing over outfits, revisit this post! Want to see what everyone else is wearing? Check out some of our bestsellers here.