6 winter date outfit ideas.

Oh, finally date night is here. Or “oh shoot, date night?!” Either way it’s a nice little break from the regular run of things. Let’s take a look at what we can wear.

First off, where’s the date? That determines the type of outfit. Are you trying to dress up a bit more than usual? Is there some kind of dress code? Is it a date at a wine bar, a brewery, a restaurant, the local cafĂ©, a stroll around the mall or a walk around the local park? All of these signify different outfits.

Best winter outfits for a first date.

Oh boy, the first date. It’s always way more stressful in the moments leading up to it and once it’s in motion, it goes the way it goes. First dates can be a lot of fun. Some more than others, but what we want to focus on is what we can do best to prepare for a smooth and easygoing date. Here’s some options to make sure you look great no matter what.

Tunic and skinny jeans.

Without fail, a trusted flannel tunic and skinny jeans will be a great combo. It’s the perfect outfit for a casual date. You’ll look and feel confident without coming off like you’re trying to upstage the entire restaurant. You can do that another time.

The slimming fit will lengthen your look, while the flowing tunic adds a bit of coverage. You can bring a long coat and wear your favorite ankle boots. It’s an unpretentious and classic look that can always sway in your favor.

Sweaters can also be sweet.

Scoop up your favorite sweater whether it be a V neck, crew neck, or boat neck. Avoid anything that your grandmother knit for you as the sentiment it brings will focus all the conversation on how great your grandmother is. Or was.

The right sweater will be as comfortable as you are and to be as naturally confident as that will say plenty to your date. Match with a pleated skirt or skinnies and you can talk about how lovely your grandmother is on the next date.

Made last minute plans and you’re in your work clothes?

Sometimes plans get moved around and your date asks: “Can you do tonight?” You check your hectic schedule (re-watching a show for the fourth time around) and respond that you’ll probably be available.

It’s not that your work outfit is terrible or anything, but you still want to leave an impression. And stopping at home before you go may not be as doable as you’d like. Keeping a colorful scarf at work is a lifesaver in these moments. It adds that extra oomf when you need it.

From the 10th date and beyond.

You’re going out with your significant other and while you’d love to go on these dates more often, time just slips by and somehow a month or two has passed without a proper date. And just because it’s winter doesn’t mean you shouldn’t go out on one!

Here are a few outfits that will relight that candle.

Dinner date in a sweater dress.

While you’ll be donning your best long down coat, you can stay extra warm with a sweater dress. It’s a perfect dinner outfit and your date will wish they looked as put together as you. Riding boots and Chelsea boots both pair well.

Off to see a show in a blouse and chinos.

There’s a play, show, or a musical that’s rolling into town and you got tickets because you knew it would be the perfect date night for you and your significant other.

It could be an off-Broadway smash hit, or it could be the local improv theater putting on their best monthly show. There’s rarely a dress code for these types of events but it tends to feel necessary to wear something extra.

That flowing button up blouse, a fanciful scarf (silk or cashmere), and a pair of chinos can be everything you need when you take a seat.

The at-home romantic evening.

While it’s going to be a lot of focus on the recipe, it’s nice to dress up as much as sticking around at home calls for. That flannel tunic or long dress shirt with rolled up sleeves along with leggings and wool socks? It sounds like the ideal outfit all the time. Dinner date especially.

Related Articles