Shop My Fall + Winter Outfits: Boots, Skirts, Jeans, Sweaters + More
As the crisp air of fall settles in and the first chill of winter approaches, it’s the perfect time to commit to creating your layered cozy wardrobe for the season. To make your shopping experience a little easier, I’ve put together this Fall & Winter Shopping Guide, packed with my favorite pieces for every occasion — from Thanksgiving dinner to holiday parties, winery days, festive travel adventures, and everything in between. Whether you’re looking for versatile boots, cozy sweaters, or statement skirts, here are my personal favorite fall and winter outfit essentials that will carry you through the season and those to come after it.
Let’s Work from the Ground Up… Shop My Fall + Winter Outfit Essentials
I’m starting this fall shopping guide by breaking down my closet, starting with one of the most important elements of any outfit: shoes! Let’s build your perfect fall and winter wardrobe from the ground up.
Shoes
When it comes to fall and winter outfits, the right shoes can make getting ready less stressful. I reach for From boots or a pair of chic heels for a holiday gathering, I gravitate toward versatile shoe options that can complement every occasion. From sturdy ankle boots for those crisp autumn walks to sleek knee-high boots perfect for pairing with skirts and dresses, you’ll see a lineup of largely neutral shoes with a couple statement stompers…
Pants
A great pair of pants is always essential. Look for versatile jeans in classic cuts like straight-leg or high-waisted, which pair perfectly with everything from cozy sweaters to dressier blouses for holiday gatherings. I also love mixing in a few pairs of tailored trousers or (faux) leather pants for a more sophisticated fall look that can be dressed up or down. Whatever your style, these pants will serve as the perfect foundation for your fall and winter outfits.
Skirts
Skirts are a simple way to stay cozy yet chic. Think mini skirts that pair perfectly with cozy tights or midi or maxi skirts that look chic with boots for colder weather. Plaid, leather, denim and even wool skirts are all popular choices for the season, and can be dressed up for holiday parties or dressed down for a casual brunch with friends.
Shirts
Layering is key when it comes to fall and winter outfits, and shirts and blouses are a crucial piece of the puzzle. I recommend having a mix of long-sleeve tops, neutral base layers, and statement blouses in your closet. Think cozy flannel shirts for those laid-back days at the pumpkin patch or a silky blouse that can be tucked into high-waisted trousers for a more polished look at holiday parties.
Sweaters
No fall or winter wardrobe is complete without a selection of cozy sweaters. From chunky knit cardigans to oversized pullovers, sweaters are my go-to pieces for warmth and comfort during the colder months. Pair them with your favorite jeans for an easy everyday look or layer them over a dress for something a little more festive. Don’t forget those timeless turtlenecks, perfect for layering or wearing solo during those chilly days.
Dresses
The big daddy of all great wardrobes: dresses. In the colder months, I love wearing my summer dresses with sweaters and tights to keep things fun. Floral and plaid maxi dresses as well as sweater dresses line my closet, all full of layering potential for casual or festive events and adventures. I try to keep my patterns to a predictable pallet so I can easily pair them with any jacket, sweater, or scarf.
Jackets
Jackets are really the FIRST thing most people see in your your fall and winter wardrobe. Whether you’re layering up for a snowy day or looking for something sleek for a night out, make sure you have versatile collection to make that final thought a cinch. A classic trench coat, warm puffer jacket, or chic wool coat are perfect for adding a touch of elegance and warmth to any outfit. Don’t forget a cozy faux fur or shearling-lined jacket for those colder days when you need to keep extra toasty without sacrificing style.
Hats
Fall and winter are the perfect seasons to embrace stylish hats that not only keep you warm but also add a fun finishing touch to any outfit. From wide-brimmed felt hats for a touch of boho chic to cozy knit beanies for those cold winter days, hats are a great way to accessorize while staying warm. They’re a quick way to elevate any outfit, whether you’re running errands or heading out for a night on the town.
More Fall + Winter Outfit Inspiration
Need more inspiration for your fall and winter outfits? I’ve got you covered! Check out the following links for even more styling ideas and outfit inspiration:
- Pinterest: For endless fall and winter outfit ideas, head over to my Pinterest board for curated looks.
- My Blog: Visit my 2023 Fall & Winter blog for more detailed styling tips, outfit breakdowns, and seasonal must-haves.
- Instagram: Follow me on Instagram for daily outfit inspiration, behind-the-scenes sneak peeks, and shopping links.
- LTK Profile: Shop my latest fall and winter outfits directly from my LTK profile for easy, clickable links to all my favorite pieces.
Stay cozy and stylish this season with the perfect fall and winter outfits, and don’t forget to check back for more updates as I continue to share my must-have pieces for every occasion. Happy shopping!
