Most winter dressing questions repeat every year: which colors work, what goes under a long coat, whether a beanie can look polished, and what to wear when the temperature drops. The best winter fashion ideas answer those questions with outfits you can put together from a small wardrobe of well-chosen pieces. Below are eight questions and fifteen outfits, each built around fabric, proportion and color so the result looks composed as well as warm. Short notes for the men in your life appear where they fit.
What colors should you wear in winter?
Winter light is flat and low, so color does more work than it does in summer. Rich, saturated shades and soft neutrals both read as expensive in it, while mid-tone colors that are neither deep nor light can look dull next to grey skies and bare trees.
Outfit 1: The tonal neutral. Wear camel, oatmeal and cream together: a cream turtleneck, camel wide-leg trousers, and an oatmeal wool scarf. Because the shades sit close together, the outfit looks like one long line, which suits cold weather when you are wearing layers. Texture keeps it interesting, so choose a ribbed knit, a flat-weave wool and a brushed scarf rather than three smooth fabrics.
Outfit 2: The jewel tone. Burgundy, forest green, deep navy and chocolate brown all suit cold weather. Pair a forest green cashmere sweater with black tailored trousers and a black leather belt. Keep jewelry to one metal, such as gold hoops, and let the sweater be the only strong color.
Outfit 3: The family photo palette. For family photos, choose two or three colors for everyone and avoid matching exactly. A palette of cream, camel and deep green works: you in a camel coat over a cream knit, a partner in a green sweater under a charcoal coat, children in cream and one green accent. Avoid large logos and loud patterns, since they pull attention away from faces. Choose fabrics that hold their shape in cold air, such as wool, corduroy and heavy knits, because thin cotton wrinkles quickly in a coat.
For men, the same palettes work through a navy overcoat, a grey or camel knit and dark denim or wool trousers. A single saturated piece, such as a burgundy scarf, is enough.
What do you wear with a long coat?
A long coat is the most visible piece in a winter outfit, so everything beneath it should be cut to fit its length. When the hem falls below the knee, you only see the collar, the lower leg and the shoes. Those three areas carry the outfit.
Outfit 4: The camel coat with a black column. Wear a camel coat over a black fine-knit turtleneck and black straight trousers, with black leather boots. The dark column under the lighter coat makes the look long and clean. Leave the coat open to show it.
Outfit 5: The belted coat over tailoring. A belted wool coat in charcoal or navy over a knit midi dress shapes the waist, and a long coat can otherwise hide it. Add knee-high boots that meet the hem of the dress, or tall boots with a short gap, so the leg line stays unbroken. A leather bag worn on the forearm keeps the coat’s shape visible.
Some practical points help the coat do its job:
- Keep the layers under a long coat thin. A bulky sweater under a tailored shoulder pulls the fit out of line.
- Match the shoe to the hem. Ankle boots suit a hem that ends at mid-calf, and tall boots suit a hem that ends at the knee.
- Choose a scarf in a lighter or richer color than the coat, tied loosely so the collar stays visible.
For men, an overcoat in navy or charcoal over a roll neck and wool trousers follows the same logic. Leather boots or polished lace-ups finish it.
What do you wear with a beanie?
A beanie looks polished when the rest of the outfit is tailored. A slouchy knit hat over a structured coat gives the outfit contrast, whereas a beanie over a tracksuit can look purely casual. Choose cashmere, merino or a fine rib knit in a neutral or a deep color, since thick acrylic knits tend to look bulky.
Outfit 6: The beanie with a tailored coat. Wear a grey or cream cashmere beanie with a camel wool coat, a black turtleneck, dark straight jeans and leather loafers or boots. The beanie takes the place of any extra hat and keeps the silhouette sleek. Pull it low enough to cover the tops of your ears, because that is where it does its warming work, and leave the hair down at the sides.
Outfit 7: The beanie with a puffer. A glossy black puffer in a cropped or hip length suits a beanie in cream or heather grey. Add wide-leg trousers or leather-look leggings and sleek boots. The puffer is sporty, so the polish comes from the trousers, the boots and a structured bag.
A beanie is also an accessory that pairs with gloves, scarves and bags in the same family of colors. If you are building a cold-weather accessory wardrobe, the guide to fashion accessories every woman should own covers the pieces worth investing in first.
Are Ugg boots still in style?
Yes, in the right proportions. Shearling-lined boots remain in regular use for cold weather, and the mini and ankle heights are the ones that tend to look most current. What makes them look elevated or sloppy is what they are paired with, and how much of the leg is visible.
Outfit 8: The mini boot with clean lines. Wear a pair of chestnut or black mini shearling boots with straight-leg or slightly cropped jeans in a dark wash, a fitted knit and a long wool coat. The jeans should hit at the ankle or just above, so the boot shows its shape rather than being buried under a hem. A neutral palette keeps the look intentional.
A few adjustments help the style:
- Choose a neutral color such as chestnut, black or sand, since bright colors compete with the outfit.
- Keep the trousers or skirt cut cleanly. A tailored mini skirt with opaque tights and a mini boot looks deliberate, while a rumpled hem looks careless.
- Brush suede with a suede brush and protect it before it gets wet. Water can stain it.
For men, a shearling-lined boot works with dark denim or wool joggers, a crewneck sweater and a down or wool jacket. The same rule about a clean hem applies.
What do you wear in freezing weather?
At or below 32°F, warmth comes from layering and fabric choice before it comes from any single heavy item. Three layers do the work: a thin base layer next to the skin, an insulating middle layer, and a windproof outer layer. Wool, cashmere and down insulate well, and a base layer in merino or a similar fine knit adds warmth without bulk.
Outfit 9: The three-layer luxe. Start with a thin merino base layer, then add a cashmere or heavy wool sweater in cream or grey. Wear lined wool trousers or thick tights under a wool skirt, and finish with a long down coat or a shearling-lined wool coat. Wear waterproof leather boots with a grippy sole, wool socks, a scarf wound once at the neck, and lined leather gloves. Keep the colors to two or three, such as cream, grey and black, so the layers look planned.
Plan for the parts of the body that lose comfort first. Cover the ears and the neck, wear gloves rather than carrying them, and choose boots a half size roomy enough for thick socks, since tight boots restrict circulation and feel colder.
What do you wear in 20 degree weather?
Twenty degrees is cold enough to need real insulation but still allows more flexibility than deep freeze. The three-layer approach still applies, with a little more room for style. This is also the temperature at which a sherpa jacket earns its place, because the pile traps air and feels soft against knits.
Outfit 10: The sherpa jacket outfit. Wear a cream or caramel sherpa jacket over a fitted black turtleneck, dark straight jeans and tall black boots. The jacket is bulky, so the base should be slim: a thin knit and a straight leg. Add a leather belt bag or a small structured shoulder bag so the outfit keeps its polish. If you prefer to avoid the teddy-bear look, choose a sherpa with a collared, jacket-style cut rather than an oversized hoodie shape.
Outfit 11: The knit set under a wool coat. A matching knit set, with a sweater and a wide-leg knit trouser in grey or oatmeal, is warm and looks finished. Wear it under a long wool coat with mid-height lined boots and a scarf in a richer color. Add thermal tights or a thin base layer under the trousers if the wind is strong.
For men, a sherpa-collared jacket or a wool coat over a heavy knit and thermal-lined trousers handles this temperature well, with a beanie and gloves in matching tones.
What do you wear to a Christmas party?
A Christmas party calls for richer fabric and a bit more shine than daytime winter wear. The venue often changes the answer, since a heated restaurant needs less coverage than an outdoor gathering or a house with a drafty hall. Plan the outfit for the room, and plan the coat for the walk to and from it.
Outfit 12: The velvet dress. A velvet dress in deep green, burgundy or midnight blue is among the most reliable choices for a December evening because the fabric looks luxurious in warm lighting. Choose a long-sleeve style so you stay warm indoors and out. Wear it with sheer or opaque tights, heeled boots or pumps, and gold or pearl earrings. Add a long black or camel coat for the journey. For more silhouettes, see our guide to elegant long sleeve dresses for fall and winter occasions.
Outfit 13: The satin skirt and knit. A satin midi skirt in champagne or deep red with a fine-gauge cashmere sweater tucked in is dressy without being formal. The contrast between the shiny skirt and the matte knit gives the outfit depth. Add a metallic clutch and heeled boots, and wear the same long coat over the top.
For men, a dark wool suit or a blazer and trousers with a roll neck or a crisp shirt works well. A velvet blazer in a deep tone suits a more festive event.
What do you wear to a winter graduation?
Graduation outfits have two practical constraints. A gown goes over the clothes, so what you wear must be thin enough to sit comfortably beneath it, and the hem, neckline and shoes are the only parts people see. Ceremonies can also involve a walk between buildings or outdoor photos, so keep a coat within reach.
Outfit 14: The graduate’s dress and coat. Wear a fitted knit dress or a slim dress with sleeves in a color that works with the gown, such as navy, cream or burgundy. Choose block-heeled boots or low pumps you can stand in for hours, with opaque tights. Carry a wool coat to wear before and after the ceremony. Choose a neckline that sits flat under the gown’s collar, and avoid bulky scarves or heavy jewelry that can catch on the fabric.
Outfit 15: The guest in tailoring. If you are attending the ceremony, wear a tailored wool blazer or a structured coat over a silk blouse and trousers, or a sweater dress with a polished boot. Pick neutrals with one accent, such as a deep green scarf, so you look good in photographs with the graduate. Choose shoes you can walk in, since seating and parking may be far apart.
For men, a navy or charcoal suit with a knit tie or a roll neck under a wool coat suits a daytime ceremony. Leather shoes with a good sole help on wet pavement.
If you want more cold-weather looks beyond these fifteen, the full list of winter outfit ideas that look expensive has plenty more to draw from.