Guide to Stylish Winter Layering to Stay Warm

Cold winter weather is a style and health challenge. This guide to stylish winter layering to stay warm covers the layering basics to create ageless layered looks for thermal comfort and style. A video demonstrates in easy-to-follow steps how to bundle up in chic layers. Various layering outfit ideas illustrate the concepts. Read to get inspired to stay warm in style.



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Stylish Winter Layering to Stay Warm

Of course, how long a layered look will keep you comfortable temperature wise depends on the weather. As a result, the clothing pieces and their material will differ. However, the overall concept of layering is to create several thin layers of still air. Thin air layers, namely, increase the insulation of your outfit. Consequently, layering is more than just for style.

In addition, relative humidity, wind and temperature matter. You have to use different material to create cold wet weather outfits than for dry, frigid cold air. Therefore, the material and types of clothes differ from what to wear when the Polar Vortex hits. More on cozy looks for different climates.


What To Consider When Layering for Style?

The fundamentals of stylish layering are

  • Short over long or short under Long
  • Wide on the top and slim on the bottom or vice versa
  • Color coordination
  • Accentuation of your waist
  • Dressing for your body shape
  • Each layer must stand as an outfit of its own when you plan to peel off pieces


midlife woman showing an example of color blocking for color coordinated pieces
Color blocking. The necklace ties the look together as it repeats the colors. Escada leather skirt, Hipstik pantyhose, Keep Calm T-shirt, Nordgreen watch (use code HLSTYLE for 15% off), Hermes collier de chien bangle, Rebecca Collins necklace, Nicole fall sandals, hoodie c/o V-shred



stylish layering to stay warm with short top under long tailored jacket
Example short under long. Michael Kors tailored puffer blazer, Docezza denim jacket, watch c/o Nordgreen, Judith Leiber belt, Halftee, half Tee, Hipstik tights, Musse&Cloud sandals, Banana Republic leather skirt, bag c/o R.Riveter (use the code HIGHLATITUDESTYLE to save 10%).



DIY Clip to Create a “Waist”

No waist is one of the most common mistakes in layering. The photo below elucidates a simple trick to look slim. This clip is easy to DIY. Just sew an oblong piece of fabric of about 1 ft (30.48 cm) in length together. Insert an about 4 inch (10 cm) long 0.5 inch (~1.3 cm) wide rubber band and sew the clips invisibly at the ends of the rubber band and close the fabric. Decorate according to your personal style.


DIY clip to clinch in a non-structured jacket at the waist to look slim
Illustration how the DIY clip can provide shape to a straight-up-and-down jacket


Other possibilities to accentuate your waist are using tailored pieces like a blazer or belting. More on how to best accessorize with belts.


How to Avoid the Bulk of T-Shirts to Look Slim When Layering

When you layer for style only (not thermal insulation) or you live in a region with winter temperatures above the freezing point, use halftees instead of T-shirts, or camisoles. If you are not familiar with them see my  review of a Halftee lace top and cropped Tee. If you layer for thermal comfort, use body conscious tops or leotards to look slim despite of piling up garments.


See How to Ensure Every Layer Is an Outfit on Its Own

The movie breaks a winter layering outfit down as an example of how to create stylish layers that still look stylish when you peel a layer or two off.

stylish winter layering to stay warm broken down in easy steps
Layering broken down in easy steps. This example demonstrates that peeling off layers must still lead to stylish looks that make sense.


The easiest way is to build a layered look around one color like styling monochromatic looks. In the example above, the look is styled around gray, burgundy, and green. Or work with the color blocking formula.



Layering Outfit Ideas

When you are new to layering start out with classic layering pieces like twinsets, sheath dresses, or vests. In cold climate like Alaska, puffer vests are a great option for thermal comfort. More on how to wear a puffer vest and not look fat. In windy climates, try a leather vest. More on how you can wear a leather biker vest.


motorcycle jacket worn over sweater to stay warm in windy weather
Ralph Lauren jean skirt, Hipstik pantyhose, Brooks Brothers sweater, Ivanka Trump pumps, Kieselstein Cord belt, Nordgreen watch, Hermes collier de chien bangle, purse c/o Jafferjees



Winter Office Look Layering with Sheath

Sheath dresses are layering classic that never goes out of style. They are also the most easy way to layer. The same outfit idea just in another color gives you already a new office look. But you can also layer over your sheath. More on layering with sheath dresses.


midlife woman stylish in winter layering to stay warm in a sheath dress over sweater
Calvin Klein burgundy sheath, silk pink and burgundy zebra pattern with orange roses neckerchief, GNW tight, Vince Camuto suede tall boots, Paloma Picasso kiss belt, Hermes collier de chien, and wooden chronograph c/o Jord


Stylist tip: Don’t forget that accessorizing and styling your outerwear is a form of piling up pieces too.


lady with jacket and hat standing
Calvin Klein sheath, snake skin imprint shoulder bag worn as clutch, GNW tight, Vince Camuto footwear, LeatherCoatsEtc gloves, and fedora c/o Tenth Street hats



Stylish Winter Layering to Stay Warm with Cardigans and Jacket

Midi skirt, tights, over-the-knee boots, sweater at the office and an old diamond leopard print jacket as outerwear to stay comfortable. Can you believe I have this jacket since I was a teenager?



mature woman in winter layers with leopard print, cardigan, glen check skirt, suede boots
GNW leopard print sweater worn as top, Moda International dyed cardigan worn as a second layer, Jord bamboo watch, Pendleton glen check pleated midi skirt, Dior suede boots, and Hermes collier de chien bangle



over 50 years old style blogger in diamond pattern jacket winter jacket
Dior over-the-knee boots, YSL work bag, LeatherCoatsEtc gloves, Pendleton wool midi skirt, cat print neckerchief, and barrette


Casual Posh Winter Layering

Casual Friday outfits don’t just mean jeans and T-shirt. Take a look of what weekend clothes you have in your closet and combine them for new looks for Friday at work. The outfit inspiration in the photos below brings you from office to drinks with the colleagues after work.


posh casual chic winter layering look with skirt, hood down-vest
Harley Davidson booties, Banana Republic straight skirt, Kieselstein Cord belt, Festina watch, barrette, GNW tight, R&O hoodie down vest, boot-toppers, and halftee c/o Halftee


#midlifestyle lady in posh casual winter look with vest, skirt, tights and booties
Front view of casual posh cold season layering look: Harley Davidson booties, Banana Republic straight skirt, Kieselstein Cord belt, Dionysus buckle, statement necklace, Hermes collier de chien bangle, GNW tight, R&O down vest, boot-toppers c/o My Top of the Boots, and halftee c/o Halftee


Boot toppers are great to double the insulation on your feet. More on creating mature looks with boot toppers.


How to Layer in Summer, Fall and Spring?

In fall and spring, use items from the warm and cold season. More on
transition your summer pieces into fall by layering with cold season pieces. More tips to style a summer dress for spring by layering.

More, on great summer outfits with layers to avoid a style rut.


Want style solutions for all kind of dressing situations? Buy my style recipe book How to Dress for Success in Midlife. Give yourself the gift of style.


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Photos of me: G. Kramm

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