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Winter Outfits For Work, Weekends And Going Out

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Here's what to wear this winter to look stylish while you stay warm.  Whether you're heading out or staying in, these chic pieces will help you pull together outfits even when it's freezing outide…
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Winter Work Oufits

For traditional work and professional events, I recommend classic styles and colors.  If you work in a creative field, add more color and trending styles.  (Each row in this section includes 3 pieces that would create a chic winter work outfit). 

 
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Outfit 1: Wear this cropped cashmere sweater with high waist tailored pants.  (Tip: wear a t-shirt underneath so that you don't have to wash/dry-clean your sweaters as often)
Cashmere Relaxed Cropped V-neck Sweater For Women
 
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Outfit 1: Wear this with a button up shirt, a soft silk blouse or a cropped sweater (this one has an 12" ultra high waist).
High-Rise Wide-Leg Wool Pant
 
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 Outfit 1: I find block heels (and wedges) to be most comfortable and think that the pointed toes look sophisticated under wide leg pants.
The Ardin Ankle Boot | Madewell
 
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Outfit 2: Dress up this classic blazer with a blouse and tailored pants, or dress it down with jeans and a white t-shirt.
Siena Slim Italian Wool Blazer
 
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Outfit 2: Silk is temperature regulating, breathable and natural. This blouse is machine washable too (line dry).
The Perfect Silk Shirt
 
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Outfit 2: Loafers work with both wide leg and slim pants.  They're a nice alternative to boots in the winter.
The Grayson Penny Loafer | Madewell
 
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Outfit 3: Cropped Lady jackets are trending, and look good with pants, jeans, skirts and dresses.
Cropped bouclé yarn lady jacket
 
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Outfit 3: This machine washable silk tank comes in 6 colors.  Wear it with a jacket and skirt or tailored pants.
Signature Silk Tank
 
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Outfit 3: This pencil skirt can be worn year-around and has stretch for comfort.
The Seamed Pencil Skirt in Seasonless Stretch

Winter Work From Home Outfits

These are some comfortable but professional pieces for your work from home (and ready for a video conference) outfits.  Each row of 3 creates a chic outfit! 

 
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Outfit 4: For a casual look, take a look at this soft cotton tunic shirt.  Wear it with slim jeans or pants.
Plaid Angled Cuff Everyday Tunic Shirt
 
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Outfit 4:  I like to wear clean dark jeans for casual days or work-from-home days, as they look polished and professional.  I save my embellished, frayed and distressed jeans for the weekends.
Wit & Wisdom 'Ab'Solution Itty Bitty Bootcut Jeans
 
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Outfit 4:  These penny loafers are comfortable (and waterproof for those wet winter days)…and easy to slip off when you're working alone…
Waterproof Penny Loafer (Women) - Blondo
 
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Outfit 5: I have this Tencel blend long sleeved polo in 2 colors.  They're comfortable but still look polished.
Essential Long-Sleeve Polo
 
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Outfit 5:  I have these ballet flats in chocolate raisin - I wear them with dresses, skirts, and slim jeans.
The Greta Ballet Flat | Madewell
 
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Outfit 5:  These straight leg jeans work with tunics, cropped tops and tucked-in tops.
Marilyn High Waist Straight Leg Jeans - NYDJ
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Outfit 6: Ponte pants (a heavy knit fabric usually made from a rayon blend) feel like yoga pants but look more professional.
LOFT Versa Ponte Deluxe Flare Pants
 
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Outfit 6: This cotton blend popover top can be worn tucked in or left untucked.
Cotton Blend Popover
 
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Outfit 6: Have a classic wool coat handy for when you need to run out for a meeting.
Toscana coat in Italian stadium-cloth wool blend

Winter Stay-At-Home Outfits

When you're not working and want to be comfortable and relaxed.  

 
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Outfit 7:  Soft cotton-polyester blend wideleg sweat pants for lounging.
Vintage Soft Wide-Leg Sweatpants
 
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Outfit 7:  Soft cotton-polyester cropped sweatshirt to match the Vintage Soft Wide Leg pants.
Vintage Soft Wedge Crewneck Sweatshirt
 
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Outfit 7:  Comfy sneakers with plenty of cushion.  (Tip: if you're looking for designer styles but don't need the latest releases, try Nordstrom Rack…)
Veronica Beard Lennox Sneaker (Women)
 
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Outfit 8:  The coziest slippers…
UGG® Scuffette II Slipper (Women)
 
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Outfit 8:  I wear these all year around! They're incredibly soft and comfy.
Women's Stretch-Knit Long Sleeve Bamboo Pajama Set
 
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Outfit 8:  A cozy robe for chilly mornings…
UGG® Marlow Double Face Fleece Robe
 
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Outfit 9:  Tired of sweat pants?  Try a sweatshirt dress with tights or leggings…
Cozy Karma 1/2 Zip Dress
 
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Outfit 9:  Lightweight, washable, super comfortable shoes (I have 2 pairs!)…
Women's Tree Runners - Jet Black (White Sole)
 
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Outfit 9:  Lightweight leggings for yoga or to wear under a dress…
Transcend High Rise 7/8 Legging

Winter Dinners, Date-Nights, And Parties

Dressing up in the winter (especially if you have snow) can be tricky.  Here are some outfit ideas as well as a few little tricks to staying warm.  

 
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Outfit 10:  Beautiful, embellished cashmere cardigan to wear with pants, skirts and dresses.
Brushed cashmere embellished cardigan sweater
 
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Outfit 10:  These faux leather pants create a cool contrast to your brushed cashmere sweater…and they'll keep you warm!
J.Crew: High-rise Bootcut Pant In Faux Leather For Women
 
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Outfit 10:  Camisole or strapless - wear it your way!
By Anthropologie Strapless Velvet Burnout Dress
 
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Outfit 11:  A classic topcoat with fur trim to kee you warm until you are indoors…
Collection Savoy faux fur-trim topcoat in Italian wool-blend melton
 
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Outfit 11:  Wear tights under this velvet dress to keep you warm.
The Katerina Button-Front Dress: Velvet Edition
 
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Outfit 11:  These fitted knee high boots won't add any bulk under your dresses.
Silent D Komass Knee-High Boots
 
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Outfit 12: Stylized kitten heels are trending, and the pointed toes look fabulous with split hem pants.
Michael Kors Women's Luna Pointed Booties
 
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Outfit 12: It's not leather or pleather.  It's a stretchy knit.  Use my code NIPA20 for 20% off until 12/31/24, NIPA10 for 10%off from 1/1/25. (#affiliate #clarasunwoopartner)
Liquid Leather™ Signature Jacket - Merlot
 
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Outfit 12; Ponte is a heavy knit so these pants won't cling or show lines.  I have this pair and wear them all the time!  Use my code NIPA20 for 20% off until 12/31/24, NIPA10 for 10%off from 1/1/25. (#affiliate #clarasunwoopartner)
Ponte Knit - Kick Front Slit Pant - Black

Winter Workout Outfits

Whether you're heading to the gym or outside for a run, these layers will keep you warm when you need it and cool when you don't.  Each set of three makes an outfit!  

 
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Outfit 13: Affordable, quality workout wear.  One of my GAPfit leggings is over 10 years old…
GapFit Lightweight Performance Leggings
 
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Outfit 13: Cute, affordable scuba half-zip in lots of bright and neutral colors.  Wear it as a cover up or under a jacket when you're out walking.
GapFit Scuba Half-Zip Pullover
 
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Outfit 13: Affordable top made mostyly with recycled polyester.
GapFit High Neck Cropped Brami
 
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 Outfit 14: A light layer that you can wear under your coat…
Salutation Jacket
 
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Outfit 14: One of my favorite leggings for yoga, walks, and errands.
lululemon Align™ High-Rise Mini-Flare Pant *Regular
 
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Outfit 14: A cozy puffer to get you to and from the gym/studio or for your winter walk…
StretchSeal™ Sleet Street 600-Down-Fill Jacket