Dress to Impress With These 5 Valentine's Day Outfits

Full disclosure: figuring out what to wear for Valentine’s Day is tough.

After all, it doesn’t matter whether you’re heading out on a first date with someone new or you’re about to participate in your 148th date night with your partner.

Either way, you still want to make a good impression and show the other person that you care. Right?

Dress to Impress With These 5 Valentine's Day Outfits

(Please note that this post contains affiliate links, which help us to run this site at no extra cost to you! For our full privacy policy, please click here.)

Contents

What to Wear on Valentine’s Day 2020

Before you even can begin raiding your wardrobe for appropriate Valentine’s Day outfits, ask yourself the following questions.

1. Where Are We Going?

First things first, what are you going to be doing on your date?

Are you going rock climbing at your local leisure centre? Will you be stargazing in the park? Or are you having a traditional Valentine’s Day dinner?

Needless to say, all of these occasions call for very different outfits. A fancy frock wouldn’t work for go-karting just like jeans and a t-shirt might look a little out of place at a five-star hotel bar.

Whatever activity you’ll be doing, make sure your clothing is suitable and you’re off to a great start.

2. What’s the Weather Going to Be Like?

Let’s face it, the British weather likes to surprise us.

It’s all well and good heading to your date without a jacket only to get soaked from head to toe because you didn’t realise that you were going to be caught in the middle of a torrential downpour.

One word: oops.

Even though it happens to the best of us, it’s better to be safe than sorry. Therefore, become a weather expert on the day’s predicted activity and you won’t go far wrong.

3. What’s the Look That I’m Trying to Go For?

There are various types of Valentine’s Day outfits so it’s important to establish what kind of mood you’re going for.

Do you want to look bold and sassy? Flirty and feminine? Or cute and simple?

You can then build an outfit that matches how you’re feeling.

Valentine’s Day Outfits That Wow

Still struggling? Not to worry – check out the following Valentine’s Day outfits for inspiration.

1. Jeans and a Nice Top

Firstly, don’t dismiss the classics, i.e. those trusty little outfits that work every time.

After all, there’s a multitude of different dates that you could go on. But the fail-safe option tends to be jeans and a nice top. It’s smart-casual, effortless and easy to style.

This year, opt for straight-leg jeans like these Topshop Bleach Jeans. Then pair them with this Lorna Luxe ‘Windsor’ Puff Sleeve Top and flats for a cinema trip.

Alternatively, elevate your look with heeled court shoes for dinner or drinks if you want to make your date swoon.

2. A Pretty Dress

Another classic, a dress with a pretty print or detailing can be perfect for fancier venues.

Simply layer this M&S Animal Print Midi version with a faux leather jacket, Doc Marten boots and plenty of attitude for a grungy AW19-inspired look.

Alternatively, swap the dress for the Topshop Spot Angel Sleeve Midi, boots for heels and the leather jacket for a faux fur coat if you want to epitomise chic elegance.

3. A Bold Jumpsuit

If you’re not into dresses, no big deal. Try a fun jumpsuit instead.

This Nasty Gal Polka Dot Jumpsuit is just as playful as it is daring and will help you embrace your inner maximalist when paired with white heeled boots.

On the other hand, dress down a solid staple like this Topshop Khaki Boiler Suit with chunky trainers and this Missguided Borg Teddy Trucker Jacket. This provides a cosy, comfy alternative that’s ideal for the pub or a casual dinner.

4. A Satin Midi Skirt and Laid-Back Tee

One of our favourite Valentine’s Day outfits for the last couple of years is a satin midi skirt with some kind of casual tee.

If you want to champion casual cool, try a plain, comfy version like this M&S Pure Cotton T-Shirt with this Topshop Dusty Pink Satin Skirt and trainers.

Not into neutral minimalism? No worries – you could always opt for a graphic or slogan tee like this Nasty Gal Open Road Biker Tee and add heeled boots to channel fierce femininity.

5. Two-Piece Tailoring

Finally, two-piece tailoring is an androgynous take on traditional Valentine’s Day outfits that I’m absolutely obsessed with.

An oversized blazer with matching wide-legged trousers, like this ASOS Design Lilac Dad Suit, will nod to AW19 trends while turning heads.

Likewise, a fitted check blazer with a corresponding skirt, like the ASOS Design Candy Check Suit, will make your life easier if you have to go to the venue straight from the office.

Either way, team both options with heeled sandals for a fresh, fashion-forward look.

Styling It Up for Valentine’s Day

Even though the bottom line is that it doesn’t really matter what you put on because your date is going to love you regardless, sometimes we rely on fashion for a much-needed confidence boost.

But keep in mind that it’s not always about the clothes you wear.

Accessories are a great way of adding little touches to your Valentine’s Day outfits to dress them up or showcase your personality.

Just pick out the items that you feel comfortable in and help you to be your best self – and you’re bound to make an impact on your date.

What do you think of these Valentine’s Day outfits? Do you know what you’re going to wear this year?

Katie Davies

Katie Davies is the Yorkshire-based freelance writer who founded Trendy Tourist. In the last four years, she has written for over 100 companies on a range of subjects, from fashion to marketing. When she’s not producing content, you can find her shopping, exploring a new place or sitting somewhere having a cup of builder’s tea.

Explore

Connect

Dress to Impress With These 5 Valentine’s Day Outfits