9 Easy Outfit Ideas Which Will Make You Feel Your Best On A First Date

Knowing what to wear on a first date is no mean feat. With the added nerves and apprehension, it’s a recipe for frantic last-minute wardrobe scrabbles. Pre-first-date nerves are a rite of passage, but another concern is knowing where to start with your fashion choices. What I learnt most from working in the fashion industry, was the importance of comfort and contrary to popular belief, that philosophy extends to date dressing. As the result of far too many saccharine rom-coms, (conveying the lengths women go to appease a lover), the context of date dressing has become scrambled.

Although we’re familiar with donning towering heels and tentatively skipping pavement cracks, the reality is that in those situations you’re less likely to put your best foot forward. I used to think date dressing was akin to one of the two – either figure-skimming cuts or flirty tea dresses. Although there’s value in both, date dressing is whatever you make of it.

When it comes to dressing for a first date there’s a general rule of thumb I think always works. Firstly, the art of subtle elevation. Much like the no-makeup, makeup look there are little details that’ll quietly elevate a look – like jewellery, a plush bag, or tailoring with strappy heels. Secondly, comfort. If you’re not a heels wearer, switch footwear for something you feel relaxed in. Slip-on flats are equally chic.

Dressing for all eventualities is a form of empowerment. Of course, the type of date has a bearing on your outfit choice, as you’re less likely to turn up to a picnic in 10-inch stilettos (although if that’s what you fancy wear them with pride!). There’s an evident playfulness with this season’s most famed pieces—cut-outs, minis and ankle strap heels, so there are various options if you’re looking for something alluring. I believe that the bones of a woman’s wardrobe are the best fashion allies when we want to look and feel our best. The oversized shirt and jeans, a daytime midi, elevated with sleek accessories, or tailored trousers paired with a décolletage-bearing top.

When it comes to dressing for dates, it’s just as much about feeling you, as it is anyone else. If you could do with inspiration for date outfits, or want to refresh your wardrobe, we have 9 outfits that’ll take you from date to night.

Style Notes: You can always count on a two-piece to look good from day-to-night. This outfit is one to go with if you want to look uniform in very little time.

Christopher Esber is the designer of the year and many more to come. I’m almost certain.

The lyocell and cotton blend will keep you cool throughout the night.

Free People pieces are available in UK sizes 4-20.

A classic wide-leg trouser in natural linen.

The quality IRL looks so great.

Style Notes: A slip dress and blazer are two of the most hardworking fashion items. For the evening, wear the blazer over your shoulders and show off every inch of the dress.

A classic for dates, work and weekends.

A silky dress is the very epitome of hard-working clothes.

The ’90s cowl neck has made a reappearance.

The criss-cross ankle strap works well with midis.

Handcrafted in Spain from old ribbons.

Style Notes: Summertime means more outdoor dates. Gingham and crochet are perfect ways to upscale a daytime look. Juxtapose the cotton fabrication with chunky clogs.

Gingham is a classic print – perfect for picnics under low light.

Although crochet is of the season, this is a classic piece.

I had a pair just like this 13 years ago. I wish I held on to them.

Crossaints – best for eating and wearing.

Style Notes: Half-tuck the shirt or undo the last few buttons and tie to show off the fringing. The textures in this look round the outfit off.

I wear mine from day-to-night.

This shade of blue works so well on linen.

A basic with a tassel twist.

Flapper girl style.

This season’s newest shape and weave is stunning as always.

These platform flip flops are some of the best quality that I’ve seen.

Style Notes: Tailoring is undefeated. I’d wear this top tucked into the trousers and my hair in a low bun, to show off the finer details and jewellery.

The cut-outs turn what would have been a basic, into a stylish top.

Due to the popularity of these trousers they’ve recently been restocked.

I’ll never again underestimate the power of well-tailored trousers.

High-waisted trousers are a wardrobe staple.

The slight dip elevates this classic bag into a hammock style.

Misshapen earrings are perfect in my eyes.

Barely-there heels always take a look up a notch.

Style Notes: A swishy dress is perfect for all occasions, and this looks very comfortable. The triple front tie detail balances the proportion of fabric.

A stunning maxi with front tie detail. Also available in black.

They’re back like they were never gone.

The twisted knot handle adds some interest.

Style Notes: A formula to refer to if you aren’t a typical date dresser. A well-fitting pair of jeans and heels always looks classic. Jewellery will amp up this look even further.

It’s sleek and sophisticated. You really can’t go wrong.

Half tuck into jeans and bunch up the sleeves.

One of the best fitting jeans, trust me!

Carry divine feminine energy wherever you go.

So chic with jeans.

This shape reminds me of vintage style bags.

Style Notes: There’s a classic look about white jeans. Paired with a detailed top, it’s a good way to celebrate a staple. Mules are casual shoes, so they always complement paired-back looks.

The type of top that always looks wonderful.

A jean known for its quality and fit.

An embroidered blouse with a square neckline is a fail-safe for all events.

I’ll always be a lover of high-waisted jeans.

For weddings, dates and fancy afternoons.

A delicate chocker style necklace.

A comfortable slip-on mule.

Style Notes: A showstopping dress you feel good in will translate to confidence. A dress and bag in matching tones is a quiet nod to colour blocking.

I’m obsessed with the colour and fit of this dress!

This green is my favourite colour at the moment and as usual, Matteau can do no wrong.

Can you tell I have a thing for jewellery?

The handle detail is so sweet.

A classic shoe you’ll wear for all life events.

Coming, up: 7 Anti-Trend Outfits I’m Seeing Everyone Wear Right Now