Winter Outfit Ideas - wit & whimsy Lifestyle Blog
We have several months of winter still ahead so I thought I’d share some winter outfit ideas from years past to give you some inspo!
My style becomes even more neutrals focused in winter. I rely heavily on my collection of favorite winter coats to pull outfits together and look to accessories to make an impact more while bundled up.
You can shop pieces inspired by each of these looks in the widget at the bottom of the post.
Weekend Athleisure
This outfit is what you’ll often find me in during casual winter weekends when I go for coffee or bagel runs in the neighborhood or go on walks with friends. I grab a pair of my favorite leggings, pop on my favorite comfy walking shoes and top with a beanie and a favorite coat.
You could top this look with a puffer coat like the one below for colder days.
Trousers + Converse
A go-to day to day look for me in winter is a favorite pair of trousers. I’ll often wear trousers with Converse sneakers but also ballet flats.
Leather Pants + Sneakers
I love dressing up and dressing down faux leather pants in the winter. For dressier looks I add a favorite dress bootie but for daytime outfits, I reach for a pair of sneakers.
A Neutral Color Palette
I love mixing and matching neutrals in the Winter. Ivory, camel, black and even gray all pair beautifully together and are such a cozy and warm way to pair an outfit together.
Quilted Jacket
A chic quilted jacket adds a polished yet sporty flair to any outfit!
Riding Boots + Wrap Coat
A good pair of riding boots paired with a simple wrap coat is great for extra cold days.
Sweater Dress and Over the Knee Boots
Sweater dresses are one of my most reliable looks for dressier occasions in winter. But I often see them styled improperly so if you’re looking for some inspiration, don’t miss my How To Style Sweater Dresses guide.
Baseball Cap
When I don’t want to wear a beanie, a baseball cap is one of my favorite winter accessories!
Plaid Coat and Black Jeans
When you’re bored of neutral coats, a plaid coat can be such a nice palette cleanser. Abercrombie and Sézane have good options. I usually pair mine with a pair of black jeans and boots.
Black and Gray Color Palette
Another color combination I love in the winter is black and gray.
Sherpa Coat
Cozy and stylish, I love the juxtaposition of pairing a casual sherpa coat with a dressier boot.
Mini Skirt + Riding Boots
I love pairing my favorite knitwear with a mini skirt and riding boots for days with meetings but plans at night, too.
Don’t forget a good pair of tights with this look!
Cropped Winter Jacket
When I don’t need something full length, a cropped black coat paired with a cashmere scarf does the trick.
Knit Midi Skirt
If you prefer a longer skirt length, try a tea length midi skirt in a heavier knit for a chic statement.
Faux Leather Pants and a Cropped Coat
Perfect for evenings out in winter just top the above look with a heavier weight wrap coat over it.
These are my favorite leather pants. Wearing an 8.
Dark Florals + A Blazer
While I often reach for florals only in spring and summer, I love the contrast of a floral in a darker shade and topped with a heavy weight wool blazer and paired with suede boots.
Lug Sole Boots
My favorite lug sole boots are waterproof which makes them exceptionally handy during rainy and snowy winter days. I pair mine with my favorite pairs of jeans that hit right at the top of the boot shaft.
Striped Sweater
A great way to add visual interest to a winter outfit under a coat is a striped sweater. This brand makes my favorites.
Navy and Black Outfit
If bare ankles are possible, I love loafers with leather pants and then a navy jacket. It’s such a stylish, timeless and very French inspired color palette for a winter outfit.
. . . Below I have curated a variety of items from brands I love – and many pieces I own myself and are seen above – if you’re shopping for some new pieces to add to your winter wardrobe. These pieces are versatile and will no doubt help you as you put together winter outfit ideas this season!
Shop Winter Outfit Pieces 
Hope this helps you guys as you get up, get dressed and get out the door!
Do you have a favorite look from the above? Would love to hear in the comments below.
You May Also Like:
- My Favorite Coats for Winter.
- How To Style Sweater Dresses.
- The Best Shoes to Own for Fall and Winter.
This post contains affiliate links. Should you purchase something from an affiliate link, I may earn commission, at no cost to you. Thank you for your support of my work!
FAQ
How do you dress seductive in the winter?
Look for fabrics or prints that you find sexy, like leopard print, or velvet. I’m also a big fan of tight warm clothes, like leggings under a mini-skirt, or a tight black turtleneck sweater.Dec 10, 2020
How to look hot when its cold?
Layering. The secret to dressing hot when you’re cold is all in the layering. Layering doesn’t just mean pilling on sweaters and hoping for the best: it also involves strategically combining pieces that keep you warm while allowing for easy adjustments throughout the day.Mar 12, 2025
How do you dress seductive in the winter?
Look for fabrics or prints that you find sexy, like leopard print, or velvet. I’m also a big fan of tight warm clothes, like leggings under a mini-skirt, or a tight black turtleneck sweater.Dec 10, 2020
How to look hot when its cold?
Layering. The secret to dressing hot when you’re cold is all in the layering. Layering doesn’t just mean pilling on sweaters and hoping for the best: it also involves strategically combining pieces that keep you warm while allowing for easy adjustments throughout the day.Mar 12, 2025
What is the 3-3-3 rule for clothes?
You choose three tops, three bottoms, and three shoes, and challenge yourself to create as many outfit combinations as possible with your selections. The concept began with TikTok creator Rachel Spencer, whose nine-item fall wardrobe went viral last year.Jan 31, 2024
What outfit do guys find most attractive?
They find it sexiest when you’re wearing something that’s sophisticated, beautiful and fits your body well without showing too much skin. For example, a black dress with a modest front and an open back, or a silky blouse with a lace camisole peeking through.Apr 29, 2015
Love88s.com offers a wide selection of sexy outfits for women, including birthday and winter styles, to enhance your wardrobe.
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