Karen Millen

Winter Going Out Outfits For Dinner, Drinks & Date Nights

Just because the weather has changed, doesn't mean our plans have. Despite the cold weather blowing in, calendars remain full. From evenings out to work events to date nights, there is very much still a need for going out outfits in winter.

How To Dress For A Winter Night Out

Find out how to layer up and choose key pieces that will see you through to February. From long sleeve designs and luxurious fabrics that help block out the breeze, to outerwear and footwear that maintain an elevated edge while protecting from the elements, these winter outfit ideas will take you through every cold-weather occasion.

Long Sleeve Going Out Dresses

Long sleeve dresses are an essential when moving from dinner to drinks on chilly evenings. A mini dress styled with tights and knee-high boots, or a flowing midi dress layered beneath a classic trench coat, creates an effortless ensemble that deserves a place in every winter wardrobe.

Fabrics such as velvet are ideal for keeping warm while maintaining a polished, occasion-ready feel. Tailoring, cut-out details and statement prints also create elevated looks perfect for evenings out and events that call for something extra.

Alternatively, style a fully sequinned dress with an oversized blazer and pointed-toe heels for a dazzling winter going out outfit that feels both comfortable and confident. A bardot neckline is another elegant option, allowing you to show a little skin while remaining covered against the cool evening air.

Leather Outfits For Going Out

If dresses aren't your usual choice, or the weather simply calls for more coverage, leather skirts and trousers are perfect for winter. Easy to dress up for evenings out and just as easy to style down for casual plans or office days, leather is both durable and timeless.

Waterproof, wind-resistant and available in countless silhouettes, leather really comes into its own during the colder months. Style leather trousers or a skirt with a long sleeve blouse and finish with anything from chunky boots or loafers to sleek stilettos for a look that transitions seamlessly from dinner to drinks.

Long Sleeve Going Out Tops

Statement blouses are the perfect partner to leather separates. While long sleeves naturally offer protection against cooler evenings, high necklines provide even more warmth while bringing a sophisticated finish to any outfit.

Pair with leather trousers or a midi skirt for an elevated winter evening look, then swap for classic denim and loafers during the day for effortless versatility.

Knit Tops For Winter Nights Out

When a lightweight blouse isn't enough, consider a knit top. This doesn't mean oversized jumpers or chunky layers - instead, think refined knitwear with elevated details. Modern knit tops feature shoulder pads, sculpting silhouettes, bardot necklines, playful cut-outs and dramatic flared sleeves, offering warmth without sacrificing style.

Style with everything from tailored trousers to wide-leg jeans for day-to-night outfits that feel polished and contemporary.

Faux Fur for Cold Evening Plans

The ultimate autumn and winter evening jacket is faux fur. Plush, cosy and effortlessly glamorous, it provides warmth while making a statement throughout the colder months.

Layer a faux fur jacket over a mini dress with tights and heeled boots for date night, or wear it over sharp tailoring to add personality and texture to a formal outfit.

Boots for Going Out Outfits in Winter

Complete your cold-weather evening outfit with a pair of boots. Whether you prefer timeless knee-high leather boots or want to make a statement with embellished or diamante designs, the right footwear ensures your outfit feels polished from head to toe while keeping you warm throughout the evening.