The Lilly Dress Guide: Our Favorite Types of Dresses for Every Occasion

Dress Types by Silhouette

Shift Dresses

The ultimate Lilly icon, shift dresses drape straight from the shoulders for the perfect balance of comfort and effortless style. We’ve been wearing our shifts everywhere since 1959-ish; try a knit shift for casual days, or a crepe style trimmed in lace for cocktail hour. A nod to the mod with timeless appeal, these colorful dresses for women add a playful yet refined touch to your wardrobe.



Fit and Flare Dresses

With a fitted bodice that comes in at the waist and a fuller skirt that flows over the hips, this versatile silhouette can be dressed up or down—look for cotton or linen sundresses for casual days, or chic styles in brocade or silk for more formal occasions.



Straight Dresses

Also known as sheath or pencil dresses, these designs feature a slimmer cut that follows the body's natural line without being too tight. They’re a Lilly favorite for all the ways they can be styled and layered –play away with accessories, cropped jackets, and silk scarves.



Fitted Dresses

Designed to hug your body, fitted dresses can range from stretchy bodycon styles to more structured silhouettes that stay close to the body from shoulder through hip. We love layering these sleek styles with an elegant blazer or casual denim jacket.



Swing Dresses

Swing dresses are similar to shift dresses in terms of at ease yet effortless styling, and they also offer a breezier fit with a flared hemline. They’re great for infusing vintage charm into your wardrobe, particularly in balmy weather.



T-Shirt Dresses

A comfy essential for casual days, these every day dresses offer soft styling and some of the same appeal as your favorite tee shirt in terms of accessorizing and outfitting. Lean into their sporty side with sneakers, or wear with flat sandals for a low-key, off duty look.



Smock Dresses

Smock dresses are named for their use of smocking (see – fashion doesn’t have to be complicated!): gathered fabric often found at the bodice, neckline, cuffs, or waist. Smocked details add both stretch and decorative texture to your look, perfectly balancing style and comfort.

Dress Types by Length

Ok, let’s keep going – there’s so much to share with you. From the cheeky mini to the sophisticated maxi, every dress length offers unique style opportunities—and we adore them ALL. Here’s a closer look at the great lengths we go to for you!



Mini Dresses

These styles have above-the-knee hemlines for a fun, flirty look that’s perfect for casual summer days and dressed up nights alike. It’s all in the accessories for where you want to take it. This versatile length pairs beautifully with almost every shoe in your wardrobe, too.



Midi Dresses

Ready for another dress that can do it all? Hello midi! With hemlines that fall around mid-calf, midis offer a chic look with a little more coverage, making them ideal for many settings like brunch with friends, cocktails with colleagues, and so much more. 



Maxi Dresses

Go long! Reaching all the way to the ankles or floor, these sophisticated and flowy styles are beloved for beach wedding RSVPs and resort getaways alike. Wear a satin maxi with sparkling accessories and heels for a formal resort occasion, or a breezy cotton style with sandals for a sunny day spent sightseeing. Take a picture and send us a postcard!

Dresses by Waistline

The waistline of a dress plays a pivotal role in defining its silhouette. Here are a few of our favorites (if we had to pick…):



A-Line Dresses

A-line dresses are fitted at the waist and gradually widen towards the hem, resembling the shape of an "A." Universally flattering, this style can be a part of your wardrobe in casual and formal variations. She does it all!



Empire Dresses

Empire dresses have a high waistline that sits just below the bust, transitioning into a flowy skirt. Keep this silhouette short and sweet with a feminine babydoll dress or, dear reader, channel your favorite Regency-era moment in an empire waist maxi.



Drop Waist Dresses

Drop waist dresses have a waistline that falls lower on the hips. Try this trending style for a relaxed and modern look.





Dress Types by Hemline 

A statement hemline can transform a dress from simple to statement-making. Try out these fashion-forward options for added movement and visual interest.



Asymmetrical Dresses

For a modern flourish to a sleek look, try out an asymmetrical hemline. Asymmetrical dresses bring the drama without a lot of fuss via a hem that’s longer on one side than the other. We especially love this look in a sleek satin column dress, paired with strappy sandals or an elevated every day knit dress with chic slides.



High-Low Dresses

High-low dresses have a hemline that is shorter in the front and longer in the back. Remember – Lilly loved to throw parties that started by the piano and ended by the pool so this style is a great option for dancing the night away (bonus points: and showing off your shoes until you toss them aside!).



Tiered Dresses

For a playful, boho look with lots of volume, give a tiered dress a twirl. Layers of fabric make up the skirt in this style, creating a romantic, ruffled effect.

Dress Types by Sleeve Length

Comfort, coverage, and style are the major considerations when choosing a sleeve length. While we might like to feel the sun on our shoulders, we get that sometimes the air conditioning is a little too low. With that in mind, here are the most common sleeve styles to consider:



Strapless Dresses

Go for it! Let a statement necklace shine in these dresses or go unadorned to let your dress do the talking in this style, which leave the shoulders completely bare. 



Spaghetti Strap Dresses

With slender straps for minimal shoulder coverage, these dresses are lightweight and breezy, making them perfect for hot summer days and work perfectly with layering pieces like denim jackets or a cardigan over your shoulders after sunset.



Off the Shoulder or One Shoulder Dresses

Channel classic resort styling in an off-the-shoulder dress, which combines the sunny appeal of bare shoulders with the coverage of sleeves. For a modern twist on the style, consider a one-shoulder dress for asymmetric style.



Halter Dresses

Nothing says “Hello, summer!” quite like a halter dress and is a timeless style with vintage appeal. This breezy style is defined by straps that fasten behind the neck, leaving the back and shoulders bare.



Short Sleeve Dresses

Short sleeve dresses are versatile and can be worn for both casual and formal occasions. Try a T-shirt dress for an easy version of this look, or a ruffle sleeve style for a more romantic aesthetic.



Long Sleeve Dresses

Whether you’re seeking a sweater dress for chilly winter days or extra coverage in the sun (have you seen our UPF 50+ styles? So good!), a long sleeve dress is incredibly chic. Try a formal style with long, sheer sleeves for black tie glamour when temperatures drop (or the a/c turns up…!) and fabulous RSVPs roll in.



Now…Let’s Dress Up!

Whether you prefer the off-duty ease of a T-shirt dress, the sophistication of a maxi dress, or the playful charm of a swing dress, there's a Lilly look waiting to brighten your day. Experiment with different styles, lengths, and designs to discover what makes you look and feel your best.