The Most Stylish Fall to Winter Fashion Under $100

This winter is likely going to be different from any other winter we’ve experienced since we’ll be mostly staying inside and many of our parties will be held over Zoom or Facetime. So while it may seem futile when we’re all living in sweats and athleisure, you’ll want to adjust your wardrobe accordingly with some new fall to winter fashion – both to keep yourself warm and to brighten up those gloomy winter days.

Our favorite new looks for late fall and the holiday season this year mostly focus on everything above the waist, since that’s what is most visible on video chats; besides, most of us need a bit of a color boost due to staying indoors more often. Accordingly, here are some of the best winter fashion trends for 2020 – and every piece we’re sharing is under $100!

Fall to Winter Fashion Under $100

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Kyi Kyi Knitted Faux Fur Pom Pom Hat, $65 and Women’s Chenille Knot Headband – A New Day™, $10

Winter Fashion Hats And Headbands

We love a good pom pom hat, and this one from Kyi Kyi is super fun with its oversize multi-color topper. Headbands like this chenille option from Target are a great idea as well, plus they will help you avoid hat hair on all those socially distant walks.


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Cozy Fair Isle Blouson-Sleeve Sweater for Women, $42 and Women’s L.L.Bean Classic Ragg Wool Sweater, Fair Isle Crewneck, $74.99

A “Holiday” Sweater

We don’t mean sweaters with reindeer, snowflakes, and Santa Claus (although we don’t mind a good “ugly sweater” themed party). Love the look of Fair Isle sweaters but balk at the price tag? Pick up one (or more) from Old Navy for a steal. Or you could go super classic and preppy with L.L. Bean for a sweater that will keep you cozy and never go out of style.

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Free People Sweetheart Mock Neck Sweater, $78 and MEROKEETY Women’s Crew Neck Leopard Print Balloon Sleeve Knitted Pullover Sweater, $27.99

Oversize Sleeves

Whether you call them puffed sleeves, balloon sleeves, or just sleeves with extra volume, this dramatic look is unquestionably popular now and we love it. This Free People sweater has a flattering sweetheart detail and comes in a range of luscious colors including a great melon shade, or try something patterned like this MeroKeety leopard print sweater from Amazon – we like the deep red or olive hues for a variation on typical leopard prints, or go classic with one of the khaki or gray colorways.

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CXINS Womens Fashion Lapel Open Front Sleeveless Plaid Vest Cardigan, $28.98 and Popana Women’s Casual Sleeveless Long Duster Cardigan Vest, $18.99

Sweater Vests

These aren’t the typical argyle sweater vests you’re probably picturing. Rather, we like longer vests with dramatic collars, like this red and black buffalo plaid sweater from CXINS via Amazon. Pair with a black turtleneck and black pants or leggings and you’re all set. Still loving the tie-dye trend? Try this Popana sleeveless open cardigan from Amazon.

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Cristabelle Multi Stone Fringe Bracelet, $30 and Taneesi Fringe Necklace,Tassel Necklace,White Gold, $48

Fringe Benefits

While a fringed skirt or cocktail dress might not be in the cards this year, fringed jewelry like this Cristabelle bracelet from Nordstrom would add some fun sparkle to anything from jeans and a sweater to a dressier top or velvet blazer. Want some more drama? This Taneesi fringe necklace available on Amazon would add some serious glamour to a basic neutral or jewel-tone tee or top.

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Essie Fun for Fall Collection, $9 and NARS Velvet Matte Lip Pencil, $27

Lip And Nail Colors 

Going darker and more dramatic with your lipstick and nail polish is a classic fall and winter look, and this season is no exception. Besides, a new lipstick or nail polish can be a great cheap and cheerful pick-me-up! We love cranberry or crimson shades like Essie’s Berry Naughty for a warm deep red or Bahama Mama if you want something that leans more towards purple. And if you want to add a pop of deep fall color to your lips, Nars Velvet Matte Lip Pencil in Cruella is a versatile scarlet that works on most complexions.

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Fashion Sequin Glitter Cotton Masks for Women Filter Pocket and Filter Included, from $7.99

Statement Masks

Face masks are without a doubt the most essential accessory of 2020, so why not have fun with them? Going with some bling for the holiday season can be fun, and these sequin masks available in 16 festive colors from Amazon have a pocket for a filter (one filter is included) and the price is right at around $10.00 depending on the shade you pick.

Women’s winter fashion in 2020 is going to be different than in previous years, and while maintaining your style might be more challenging, we think it is important to change things up with the seasons and keep things fresh – not only will you look great, a new piece or simply switching up your old pieces can help elevate your mood – which can be essential during a pandemic winter.

We believe in dressing for yourself even if the only people who see you are friends and family over Zoom. How are you changing things up as the seasons shift from fall to winter? Let us know in the comments or in our Growing Younger Facebook group!

Shop Fall To Winter Fashion Under $100

–Jacqueline Zenn

You may like to read more of Jacqueline’s styling posts like How To Get The “French Girl Look” When You Are Over 40 and How To Dress for Cool Versus Warm Skin Tones.

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winter fashion under 100


4 thoughts on “The Most Stylish Fall to Winter Fashion Under $100”

  1. OK, I think I need to order everything. I LOVE the Fair Isle sweaters, the red/black buffalo check vest, the INDIGO tie-dye vest, the sequin masks….. THANKS FOR DOING THE RESEARCH FOR ME!


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