9 Easy Outfit Ideas That Will Make You Feel Your Best on a First Date

first date outfits:



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've learnt most from working in the fashion industry is 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 people go to appease a lover), the context of date dressing has become scrambled.

Although we’re familiar with wearing 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 two options: either figure-skimming cuts or flirty tea dresses. There’s value in both, but date dressing is whatever you make of it.

first date outfits:



When it comes to dressing for a first date, there’s a general rule of thumb I think always works. First is 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. Second is comfort. If you’re not a heel wearer, opt 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 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.

first date outfits:



When it comes to dressing for dates, it’s mostly about feeling like yourself. If you could do with inspiration for date outfits or want to refresh your wardrobe, we have nine outfits that will take you from day to night.

first date outfits:



1. Tie Top and Trousers

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 to 20.

2. Oversized Blazer and Slip Dress

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

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

The criss-cross ankle strap works well with midis.

Handcrafted in Spain from old ribbons.

3. Summer Dress and Clogs

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 and 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 it.

4. Linen Shirt and Fringed Skirt

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

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.

5. Cut-Out Top and Tailored Trousers

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.

Barely there heels always take a look up a notch.

6. Maxi Dress and Sandals

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.

7. Oversized Shirt and High-Waisted Jeans

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.

One of the best-fitting jeans—trust me!

This shape reminds me of vintage-style bags.

8. Detailed Top and White Jeans

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 pared-back looks.

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

9. Evening Dress With Heels

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?

Classic shoes you'll wear for all life events.

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