How to Transition Your Outfits from Fall to Winter


Fall Transition Outfits that Scream Glam

Every day you get to reinvent yourself with different outfit pairing options and so do the seasons. All seasons have their beauty but with winter creeping down into the valley of fall, no doubt you'd love the fun feeling of seeing snow better than the specs of other seasons. The outdoor transition from fall to winter is beautiful if you look beyond the freezing temps. 

From falling leaves to snow-clad streets and rooftops, you'd look more at the moment in some fall transition outfits. Don't know how to pair them? No worries, we've got everything from layers to layers with thick knits and cozy wool coats to get your winter wardrobe in the amp mode.

Under our 8-step guide on the transition of outfits from autumn to winter, we included tips on how you can repurpose much of your fall ensembles and staples you can add to form extra layers underneath your clothing. We also gave some of our top picks on fall transition outfits that you can add to your shopping list for a full revamp of your winter closet.

How to Transition Outfits from Fall to Winter

1. Start With Building Up Layers With Basic Fall Staples

Your fall clothing are functional piece when it comes to transitioning to winter. The sweater dresses, cardigans, cozy fits, and chunky ensembles can be layered effortlessly to form part of the bulk of your clothing. You can also re-purpose your spring and summer t-shirts and tank tops to form more layers under your clothes. Opt for jeans and leggings from your fall wardrobe to get more outwear.

2. Gradually Add Heavy Knit Sweaters and Knit Dresses to your Wardrobe 

Thick pants and dresses made from wool, knits, and cashmere should be introduced to add warmth and a cozy feel to the entire clothing. Sweaters, coats, and cardigans serve as great layering pieces and also help in the fall outfit transition. Hoodies and button-down shirts either flannel or plaid help create a casual outlook.

3. You Don’t Have to Ditch All Your Summer Clothes

While the temperature is dropping, you don’t have to ditch your entire summer staples for all the thick ones. For instance, you can repurpose your summer maxi dress in your transition of clothes from fall to winter by wearing a turtle neck knit long-sleeve top underneath, then a thick coat over the dress. You can imagine tights to be a no-no for fall and winter, however, you can still wear them with knee-high boots in place of your warm leggings.

4. Leave Out the Colorful Patterns 

Stick with basic items in neutral colors such as black, cream, beige, mustard green, tan, gray, brown, navy blue, and maroon.  If you have to wear florals, tone them down. Anything pastel or brightly colored would not be a good idea. But if you love to dare, you can always cross the bounds in bright shades and sparkly ensembles.

5. Experiment With Different Looks

This is quite the opposite of tip #3 above, but while fall-to-winter transitional outfits aren’t the best time for bright-colored dresses, playful patterns, and prints, they are also an opportunity to stand out from everyone else. When you want to break out from the crowd, you can choose to wear a bright color scheme or fun new styles.

6. Keeping Warm With Accessories

Beanies, chunky scarves, and berets in interesting patterns and neutral colors help ward off the cold. When wearing shorter-length clothes, opt for over-the-knee booties and leggings. Peep-toe shoes and sandals are not ideal if you want smaller shoes. Instead, go for ankle booties in black or rich brown tones.

7. Creative Styling

Apart from the warm and cozy accessories, you can add some visual interest to your looks and make daring statements with belts, sunglasses, bags, and jewelry pieces. A stylish belt can define your waist amidst the layers so you don’t feel shapeless in your outfit. Subtle jewelry is sure to give you a luxe feel even on bitter winter days. Bags and purses can help carry a few accessories and add color to your attire.

8. Pack Up Clothing You Won't Be Wearing for a Couple of Months

While transitioning into winter outfits, you would need more room in your wardrobe to accommodate the chunky apparel. For instance, the leather jackets and strappy dresses that won't be worn should be packed out of the closet and into where you put in your seasonal wear.

Transitioning Your Wardrobe to Fall and Winter: Our Top 15 Picks

1. Cozy Fall to Winter Transition Outfits

Elza Motorcycle Fur Jacket layered over a Corset Style Ribbed Long Sleeve Top and Vegan Leather Pants with Ankle Boots.

Once the temps drop, we're heading for the super cozy staples. To fit the frosty aesthetics of winter, this combo will get you at the top of it all. And if you're vibing with any of the bag trends, you may want to pull the entire look together with a fuzzy bag that gets a bit more attention than other season's bags.

2. Transition Into Winter Outfits in Unique Girly Stuff

Love a bright pop of colors for your transition? Try out a fuchsia gold buttons cardigan with high waisted split hem pants. Step into booties with a clear heel and strap a pink shoulder bag over. The beauty of fashion is that you get to try new looks each time. What's the worst-case scenario? Don't like it, so you try another combo.

3. Chicest Ways to Changing Your Wardrobe to Fall Fits

Beige Snow Bunny Vest Jacket, Neutral-toned Illias Wool Sweater, Beige High Waisted jeans, and a Pair of Nike Shoes

This blend screams "All I want for Christmas is You". Having gotten our fill of turkey, we're giving you a head start on the best looks so it doesn't get snatched up before you. This chic fit will get you in the festive spirit to switch between celebrations and transition from fall to winter.

4. Cute Transition Outfits From Fall to Winter 

Transitioning your wardrobe to fall and winter is not only about the winter coats, wool, leather pieces, cozy socks, and thick knits you've got in your closet. Stocking up more sophisticated apparel to include in your collection should be on the shopping list too. This choice of how to transition outfits for winter allows you to dazzle in the coziest showstoppers. Let's not even get started on the looks you will be serving in this two piece set paired with beige booties and a bag .

5. Winter-Fall Wardrobe You Won't Care It's Freezing

Green Bandit Bomber Jacket, White Knit Top, and High Waisted Jeans 

Why not go bigger on your jacket selections since they're having a moment now? An added cool factor specially made for your fall wardrobe while waiting for winter. This Bomber jacket and a long sleeve top have a great touch when worn together.

6. Transition to Winter Outfits in Plush Vibes

Avelle Vintage Cropped Plaid Jacket, Pink Bella Oversized Knit Sweater, and Skylar Wide Leg Jeans

This Vintage plaid jacket will look amazing on you and is one of the cute ways to include the 80s fashion vibes in your fall and winter looks. If Vintage is not entirely your style, you could try the Lindy Oversized Plaid Jacket. Still in the falling leaves mood of autumn? Try on a flower print sweater.

7. Going From Transitioning to Wearing in Fun New Outfits

Purple Miranda V-Neck Cardigan over a Strapless Vegan Leather Dress in Beige with Tights and Over the Knee Boots.

A cute combo for transitioning to winter while bringing in innocent looks. Wearing a strapless dress in winter may not sound like one of the best choices, and though the cardigan offers some coverage, we advise you to try this while it's not yet snowing.

8. How to Transition Outfits for Fall To Give Off Boss Vibes

Beige Alora Aviator Jacket, Black Knit Dress, with Ankle Boots

Whether you want to look super snatched while stepping out between winter and fall or you're wondering what outfit would work for both seasons, this Beige and black combo is simply the best way of creating a subtle statement while keeping all eyes on you.

9. Cute Fall Transition Outfits that Every Girl Loves

Tap into your softer side in the baby doll Jessy Shirt Jacket over an Amabella Soft Cardigan. If it's not very frosty yet, wear a shirt dress and layer with a plaid jacket. Switch the jacket with a houndstooth sweater to create exactly cute attire.

10. Best Transition Dressy Casual Outfits Fall to Winter

Black Juniper Long Sleeve Bodycon Dress and Verona Wool Coat 

The perfect boss lady fit for transitioning to winter – this bodycon dress with warm lining and wool coat are all you need to step into an event during the chilly season. Need the confidence to enter into any function? The black beret is the only accessory you need to surprise them.

11. Easy Fall to Winter Transition Outfits

Knit Off Shoulder Sweater Dress

When planning your transition of clothes from fall to winter, sweater dresses should be among your top picks. The orange color blends well with the fall color palette and the fabric provides some level of warmth when it gets freezing. The off-shoulder detail makes the outfit look even more feminine and charming. You can layer a warm coat over the dress for extra coverage from the freezing temps.

12. Fall to Winter Transition Outfit Inspiration

Sonet Knit Dress with Vegan Leather Double Breasted Trench Coat

A long-sleeved thigh-slit midi knit dress, beige pointy-toe boots, and sleek jewelry pieces can be the perfect outfits for the fall-to-winter transition. If you're not sure what the weather will be like and you're heading out for the morning, grab a coat, which can be fur, wool, or leather. Even if it's just windy and not very chilly, still grab a coat.

13. Transitioning Casual Clothes from Fall to Winter

Cece Knit Sweater Dress

The Fall to Winter period is obviously cold weather times and it is only ideal to keep yourself fully clothed and warmed up with thick knits and cozy layers. We love this knit sweater dress because of how practical it is in Fall and winter. Plus there are different color variations that you can choose from to prepare you for the cold in your fave shade.

14. Transition of Clothes From Fall to Winter

To help you get winter-ready while staying warm and stylish, opt for this long sleeve knit dress. When it becomes very cold, layer a coat or jacket over the dress. You can pair the outfit with a hat  and boots for a chic cozy statement.

15. Transition of Outfits From Autumn to Winter

Mally Faux Mink Fur Cardigan

You can't fault in creating a fun comfortable look with a faux fur cardigan. You can throw it over your colorful knit dresses or your mock neck tops. They are super comfy and perfect for when it's mildly chilly and windy.

Frequently Asked Questions:
When should you remove fall clothes?
The sweater weather and boot season are up for a full revamp into the ensembles of the much cooler season between mid-September and early October. By this time, you should start setting up your winter wardrobe. If winter doesn't come as fast as you thought, then you should leave transitioning till when the temperature hits between the 60s.
How do you change fall clothes for winter?
To transition your wardrobe from winter to spring, start by incorporating lighter layers and brighter colors. Swap heavy coats for lighter jackets, and pair sweaters with skirts or lighter pants. Florals and pastels are perfect for this transition.
What kind of clothes to wear in spring?
In spring, opt for lighter fabrics and layers. Dresses, skirts, and light sweaters or cardigans are ideal. Choose bright colors, pastels, and floral prints to reflect the freshness of the season
How do you wear a dress in fall and winter?
To wear a dress during the cold weather and not freeze, ensure you choose one made from a warm fabric. Think heavy knits, sweaters, velvets, wool, and the likes. If it's very cold, you should wear it with an overcoat and step into comfy shoes.
What is a transitional outfit?
A transitional outfit is a cloth that you wear from one season into another without having to shop a whole new wardrobe collection. For instance, it may be that you're repurposing some of the clothes from the previous season (Fall) for the early days of the next season (Winter) and styling them in such a way that they will be suitable for the next season (Winter).
Rate this article, if you like it
Leave a comment
All blog comments are checked prior to publishing
[time] minutes ago, from [location]
The cookie settings on this website are set to 'allow all cookies' to give you the very best experience. Please click Accept Cookies to continue to use the site.
You have successfully subscribed!
This email has been registered
Recently Viewed