The Top 10 Transitional Dress Trends for Cold-Weather


With different silhouettes, lengths, fabrications and trends, knowing what dress is right for you can be challenging – especially during those awkward transitional months where the sun is still out but rain and wind could be around the corner at any moment. It’s when a cozy jacket might seem like the way to go in the morning, but by the time you pop out for lunch, you’re breaking a sweat. But that doesn’t mean you have to swap out your dresses just yet. No, with one or two items and some styling (more on this later), you can make what you already have work.  

Whether you’re in need of minimalist dresses, perfect for work and the weekend or look-at-me numbers that encourage a double take, our edit of fall dress trends will have you covered. Keep scrolling for this year's must-have styles. 

10 Cold-Weather Dress Styles You Can Make Work for Any Occasion or Mood 

The Perfect Midi Dress 


Falling between the knee and ankle, the midi dress — derived from the word “middle” — describes a dress length that is in the middle of a mini (above the knee) and maxi (pass the ankle) dress. Midi dresses can come in A-line, fit-and-flare, and more. An A-line midi, perfect for both casual and semi-formal occasions, is fitted at the bodice and flares out at the waist creating an “A” shape. Whereas fit-and-flare midis have a very pronounced flare in the skirt that adds a playful touch to a look and is great for evenings of dancing.  

Midi dresses can be dressed up with pumps or down with flats. With sleeveless, short- and long-sleeves, they are the one-and-done option that can be worn year-round. Plus, there are many options to winterize a midi dress: simply add a cable knit or turtleneck sweater and finish it off with knee-high boots; or layer it with a fashion-forward cardigan.  

The Professional Pleated Dress 


A pleated dress with fabric that is gathered or folded to create pleats, adds great texture and movement to any outfit. Still holding onto summer prints? No problem. Add in a playful knit or chunky sweater, knee-high boots and your pleated dress quickly becomes part of your cold-weather arsenal.  

The Evening Off-The-Shoulder Dress


The bare shoulder trend that was popular in 2010 is experiencing a renaissance. Delicate exposing of the shoulders is the foundation of the off-the-shoulder dress. Romantic enough for date nights and polished enough for galas and formal events, the off-the-shoulder dress looks great with strappy sandals, gold accessories, and a statement lip.  

The Statement Occasion Dress


The secret to successful soirée dressing lies in occasion dresses. Whether you opt for lace, ruffles, padded shoulders, tasteful cutouts, or bows — this year, getting full-glam is anything but boring.   

The Classic LBD


What does Princess Diana, Marilyn Monroe, Audrey Hepburn, and numerous other women of power have in common? Their love for the sharp and timeless, little black dress, more commonly known as, the LBD. Since 1926 when designer Coco Chanel created the shape, Vogue editors declared it would “become sort of a uniform for all women of taste.” And it’s true, each season is filled with closet classics we return to time and time again, and the LBD is certainly one of them.  

Working as a blank canvas, fashion icons have proved the LBD can be reinvented over and over again. With the change of jewelry or hairstyle, it can be worn to weddings, the office, and date nights. Styled with black tights and an evening bag or color-pop jewelry, the versatility is endless.   

The Fashionable Pattern Dress


Available in tweeds, floral, checks, white + black stripes, and more, showcase your personality at work in a timeless patterned dress. Remember to add in accessories (think tote bags, cat-eye sunglasses, and statement jewels) to make your winter look stand out. Or dress it up with strappy heels and a clutch for more formal events. Style yours with a jean jacket on a cool fall night. 

The Works-Anywhere Wrap Dress


A wardrobe staple since the ‘40s, the wrap dress is quintessential for work and play. Not only does it define your shape with the cinched waist, but it brings structure to your look. And fortunately, from cotton, denim, ribbed, and utility-inspired, the options run the gamut.  

The Playful Mini Dress


For a spirited and playful dress, look no further than the mini, an above-the-knee dress that hits around mid-thigh. Teamed with a blazer or cardigan, the mini is great for nighttime events, and casual days when paired over denim or under your favorite tee.  

The Endlessly Versatile Shirtdress


Originating in the ‘60s, the shirtdress, a menswear-inspired style is the all-in-one-outfit dress you need for the transitional months. Seasonless shirtdresses are some of the most comfortable silhouettes. With a collar that elevates the neckline — you will look polished and put together with minimal effort. In the colder months, you have options for wool blends, corduroy, silk, denim, and knit. Pro tip: Keep your favorite shirtdress on rotation throughout the colder months by slipping a thin base layer underneath it. 

The Powerhouse Sheath Dress


Featuring sculptural necklines, waist details, and minimalist lines, sheath dresses, form-fitting styles that hit at or above the knee, are a sure-fire way to win at career dressing.  

When Should I Change My Seasonal Clothes? 

Although it’s not quite time for the annual “changing of the guard” from your summer to winter wardrobe, now that you know when to wear and how to style transitional dresses, how can they be adapted into the winter season? Thankfully, there’s no shortage of formulas out there that you can use to guide you through the process.  

You have the option to style your favorite dresses over pants. A little unconventional sounding? Maybe. But over the years, the fashion set has hung onto this styling hack. Simply pop the dress over denim or printed trousers and create a whole new look. Or go the minimalist route and add in a turtleneck. The wardrobe staple is tight-fitting, for an endlessly smooth fit underneath dresses and can be paired with an oversized blazer or your favorite outerwear for extra warmth. A sweater vest also creates a winter vibe when paired over a go-to dress trend. 

Getting dressed or going shopping for the fall and early cold-weather season can be a lesson in trial and error. But luckily for you, our physical stores and online assortment has got you covered. After all, transitional dressing should be exactly what it sounds like – clothes that help you effortlessly transition from summer to fall or fall to winter, without the need for a whole new wardrobe. When the forecast is in flux, the only way to win with transitional dresses is to arm yourself with a solid foundation of wardrobe essentials — think blazers, chic cardigans that can be worn alone or layered together, knee-high boots and more.