#Street Style

10 Fail-Proof Formulas for Winter Work Outfits

by Emily Tozer

10 Fail-Proof Formulas for Winter Work Outfits

It takes a few key pieces and a special knack for layering to come up with winter work outfits that are both comfortable and professional-looking. Let these fashion bloggers help with 10 outfit formulas you can rely on this season.


Tailored Coat + Blazer



When it comes to layering with winter work outfits, think clean-lined rather than cozy. Start with your basic blouse and skinny jeans or pants, add a structured blazer, and finish the look with a tailored coat like Sheryl of Walk in Wonderland. The result is just as warm as a chunky sweater but way more professional.


Blazer + Midi Skirt



If you need winter work outfits that are more conservative, there are still plenty of ways to inject a little personal style. For starters, trade the tired suit for a bold, pinstriped blazer and a colorful midi skirt as Margaret of Shine by Three does. We love how she breaks up the jewel tones with a crisp white shirt, cleverly half-tucked to emphasize the look’s long layers.


Long Cardigan + Skinny Pants



A maxi-length cardigan is the perfect cozy layer for winter work outfits. Re-create this look seen on Helena of Brooklyn Blonde for your next casual Friday: a long cardigan, a basic tee, and skinny pants in neutral hues.


Statement Jacket + Flare Jeans



We’re all about winter work outfits that incorporate this season’s ’70s trend. Dress up a pair of flare jeans with a statement jacket and a simple blouse as Olivia Palermo did. Pointed boots will give the illusion of longer legs plus help keep you warm!


Shirt Dress + Tailored Vest



Layering will easily extend the wear time of your dress collection to winter work outfits. Pair a warm, tailored vest over a fluid shirt dress as Samantha of Could I Have That did, adding tights or boots if the weather warrants.


Turtleneck Sweater + Tapered Pants



Swapping a few basic workwear staples will do wonders for your winter work outfits. Slip on a textured turtleneck sweater, as Mary of Happily Grey did, instead of a silk blouse; and try tapered wool pants instead of a skinny or straight pair.


Chunky Sweater + Pencil Skirt



Try reworking office staples like the pencil skirt for easy winter work outfits. A turtleneck sweater over a basic white shirt and tall socks with pointed ankle boots are both warm and stylish. For the most professional look, opt for layers that are streamlined and in a simple color palette as Kimberly of Penny Pincher Fashion did.


Tailored Coat + Double Denim



Take a styling note from Pam of The Girl From Panama to update double denim for the colder months. A long, tailored coat, a textured scarf, and ankle boots are perfect additions to this classic outfit formula. Clean—not distressed—dark or black denim washes are best for work.


Poncho Sweater + Wide-Leg Pants



Nothing is easier on late mornings than an all-black work outfit. Change up your usual pairing with an infinity scarf or a cozy poncho sweater on top as Krystal of This Time Tomorrow did.


Tweed Jacket + Leather Skirt



Step up your winter desk-to-drinks outfits with luxe pieces like a tweed jacket and a leather midi skirt. In coordinating jewel tones, the pairing is equally sweet and smart on Jenny of Margo & Me.