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 5 step guide to transitioning your wardrobe from fall 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 is functional pieces 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 cloth. 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. 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.

4. 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 toes shoes and sandals are not ideal if you want smaller shoes. Instead, go for ankle booties in black or rich brown tones. 

5. 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 10 Picks

1. Cozy Fall to Winter Transition Outfits

Blue Fay Cropped Puffer Jacket layered over a Black Knit Turtleneck and Black Belted Jeans with Chelsea 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, then 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 red long-sleeved top with a cognac jacket. Step into pink neon boots 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, White Parachute Pants, 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 

Blue Mock Neck Top and Tan Blair Tiered Skirt With Greta Duck Down Jacket

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 that tiered skirt

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

Green Bandit Bomber Jacket, White Cropped High Neck Top, and Flared 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 crop top have a great touch when worn together.

6. Transition to Winter Outfits in Plush Vibes

Avelle Vintage Cropped Plaid Jacket, Pink Ivy 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 80's 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 Dress in Tan with Tights 

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 Midi 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 strapless romper and layer with a plaid jacket. Switch the jacket with a checkered sweater to create exactly cute attire.

10. Best Transition Dressy Casual Outfits Fall to Winter

Black Juniper Long Sleeve Bodycon Dress and Aubrey Wool Coat 

The perfect boss lady fit for transitioning to winter – this bodycon dress 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.