Your Guide to Date Night Dresses for Winter

Getting ready for a date night in summer is a breeze; slip into a linen dress and you’re good to go.

When winter rolls around, things become a little more challenging.

Thermal layers, fluffy socks, and a beanie aren’t exactly restaurant appropriate.

We get it — just the thought of a date night out in the icy elements can be enough to put you off the idea altogether. 

But hold off on sending that cancellation text. Below, we share the tried and true winter date night outfits that are both cozy and chic. 

Read on for your guide to date night dresses and outfits for winter. 

What to Wear on Date Night in Winter

Whether you’re off for a first date, a romantic night with your significant other, or a dinner date with your bestie, how you feel about your outfit can really set the tone for the evening. 

Of course, there’s no such thing as one-outfit-suits-all; it’s about what makes you feel comfortable, confident, and your very best self. 

In the depths of winter, it can be tricky to conjur up new outfit ideas. The trusty jeans, boots, and ‘nice top’ ensemble can begin to feel a little stale after a while.

If you’re in a bit of a rut, it’s time to spice up your date night outfitting with some refreshing combinations and edgy silhouettes.

Spoiler alert: even the mini dress you usually reserve for summer has a place in a winter wardrobe. It’s all about adding the right coat and boots!

How to Dress for Date Night in Winter 

Below, we unpack how to dress for a date night in winter.

From midi dresses and knee-high boots to two-piece sets and suits, we’ve got you covered no matter your style. 

Date Night Dresses for Winter

Forget what you heard about winter dresses; they don’t have to be made from a thick ribbed knit and feature long sleeves to be seasonally appropriate.

Dresses of all different lengths, fabrications, and hues can work during the cooler months — the secret is in how you style them.

Let’s take a look at how to style mini, midi, and maxi dresses for winter. 

A Mini Dress & a Long Coat

It’s the combination you’ll often see worn by your favourite celebrities and street-style influencers. A mini dress paired with an oversized coat is a seriously chic look.

The key is to keep the coat open or drape it over your shoulders to reveal the mini dress underneath. The short hem of the dress combined with the longline drape of the coat creates levels and contrast, which feels contemporary and edgy.

While most mini dresses work well in winter, avoid warm-weather prints such as florals. Instead, opt for earthier hues or jewel tones. If colour is your thing, go for a solid block colour instead. Think a bright orange, barbie pink, or bold cobalt blue.

We recommend going for a simple coat in a neutral tone, as it will pair easily with a range of different mini dresses. Our top picks are a classic beige trench or a black woolen coat with oversized lapels. Here are some great winter coats to consider.

To round out the look, add a pair of knee-high boots. It’s a good idea to colour-match your boots to either your coat or your dress, as adding a third colour will likely result in a clashing, busy look.

Slick your hair back in a low bun or ponytail for a clean and polished finish.

A Midi Dress & a Faux Fur Jacket

Midi dresses are a wardrobe staple all year around, and none moreso than the slip dress, which returns season after season to remind us of its versatility.  

The slip dress is sleek, elegant, and simple in the very best way. We love how slip dresses drape down the body to create a flattering, sophisticated silhouette.

They’re perfect for any kind of date night, pairing perfectly with heels or boots depending on your mood. Colour-wise, black slip dresses deliver the most timeless and classic look. Alternatively, go for a splash of colour and add neutral accessories for balance.

If you want to embrace your feminine side, go for a midi with ruffles or ruching. These features add an element of youthful romance and playfulness. We particularly love red or soft pink hues here.

The extra length of a midi will give you a bit of extra leg-warmth, but you’ll still need some coverage up top.

A faux fur jacket is the perfect addition to a slinky midi dress. It’s easy to throw over your shoulders, exudes glamour, and locks in warmth. A winner on all three fronts!

A Maxi Dress & an Oversized Blazer

If you’re heading out to a particularly sophisticated location, a maxi dress is an easy go-to. The longer the hemline, the more ‘formal’ a dress feels, so a maxi takes it up a notch from the easy-wearing midi.

Steer clear of floaty, lightweight silhouettes and fabrications. These are better suited to warmer months.

Instead, opt for a mid to heavyweight silk or satin fabrication, as these tend to feel a bit more seasonally appropriate (they’re warmer, too).

A maxi dress with a leg slit will pair well with heeled knee-high boots. Alternatively, slip on some mules or kitten heels for a classic look.

This ensemble can feel quite formal, so we love throwing an oversized blazer on top. This adds a masculine edge and creates a laidback finish.

Colour-wise, darker winter colours and jewel tones will always be a hit, particularly with a black blazer on top. If you want to inject a little colour into your look, go for a soft green, orange or blue dress paired with a black blazer, bag, and shoes.

If the length appeals but dresses aren’t your thing, try a wide-leg jumpsuit. The length and draping shape is reminiscent of a maxi dress, but a jumpsuit is that little bit more comfortable and wearable.

 

 

Date Night Outfits for Winter 

Not keen on dresses? Switch it up with a sleek set or a suit combo. 

Sleek Set 

Change up your winter styling with a two-piece set. The beauty of sets is the variety.

If comfort is the goal, go for wide-leg pants and a matching top. High-waisted wide-leg pants create a supper flattering silhouette by elongating the leg and cinching in the waist. Just add a blazer or leather jacket over your shoulders for added protection from that icy breeze! If you’re after a casual look, team your set with white sneakers. For a dressier take, go for mules instead.

A midi skirt and crop set work well for formal, elevated locations. As mentioned, floaty skirts feel summery, so go for something a bit more shapely and weighty. We recommend a figure-hugging midi skirt or pleated knit skirt. These silhouettes can be styled effortlessly with a coat and pointed-toe boots.

Modern Suiting 

If you feel your best in something structured, go for a suit. A blazer and pants combo ticks all the boxes: comfortable, warm, sophisticated, and flattering.

For the most refined look, keep the blazer buttoned up all the way. Or, add a cami or crop underneath and leave the blazer open for a more relaxed take.

If you’re petite and find your figure is overwhelmed by wide-leg shapes, go for tailored, cropped trousers instead.

For taller, curvier silhouettes, we love high-waisted wide-leg trousers. They work to accentuate your height and curves by drawing the eye down the leg.

The silhouette of a suit is a statement in itself, so go for a solid hue rather than a print. Opt for black and white to keep things classic, or step out in a bold red suit to make a real impact.

Add pointed-toe heels to complete the look!

Finding Your Date Night Fit 

If you’re anything like us, the idea of dropping hundreds of dollars on a single date-night outfit isn’t entirely appealing (or feasible).

That’s why we created a hiring platform. This way, you can wear designer pieces for just a fraction of the price and save space in your wardrobe.

You can hire all of the items mentioned above and hundreds more at Dress for a Night.

For a little extra inspo, discover the must-wear trending dresses of 2022.