An Editor's Guide to What to Wear on a First Date

There's one big question that every woman struggles with at some point in her life: What is the best thing to wear on a first date? Should you go classic and just stick with a little black dress? Perhaps it's more of a bold frock here's who I really am type of situation. Maybe, just maybe, you don't want to wear a dress at all and would be much more comfortable wearing a pair of jeans. However you feel about the other elements surrounding a first date (will your date be shorter than promised?), it's inevitable that you will stress out about what to wear.

But worry not—we've rounded up a few outfit ideas that will work for every kind of girl and every kind of date. There's just one rule we stick to: Make sure you feel good—and really comfortable—in what you wear. Whether that equals a comfy dress that you can wear your battered Converse with, or more girlish skirts that show off a little leg, there's plenty to chose from for that all-important first date. Click through our gallery for seven outfits that nail what to wear on a first date. Plus, you can shop the looks right now. 

Outfit #1: A Wow Top + Boyfriend Jeans


Timur Emek/Getty Images

Style Notes: Look, not everyone wants to go for the short skirt option, but there are ways of feeling date-ready without showing off your pins. Try an off-the-shoulder top and your favourite pair of jeans. This outfit is a guaranteed confidence-booster. 

Stripes are everywhere right now, so not only will this serve you for a date, it will also last well into summer and beyond. 

Pair with either your favourite flats or heels, whatever you feel the most comfortable in.

Outfit #2: Wrap Dress + Sandals


Christian Vierig/Getty Images

Style Notes: The wrap dress is a classic for a reason: It is universally flattering. Not only that, it comes in various different lengths and shapes, so it means that you don't have to show off skin if you don't want to. A simple cinching of the waist is all you need to look super feminine. 

Wear with strappy heels for the date but with a roll-neck and trainers for a brunch with friends.

An easy sandal to pair with any outfit but especially perfect for a date night. 

#3: Miniskirt + Flats + Shirt


Christian Vierig/Getty Images

Style Notes: The miniskirt made a big comeback last year; you need only see the multitude of bold patent black skirts on the market right now to know that. Pair with pretty flats and a loose blouse to ensure you don't feel too self-conscious. 

Embroidery and pink? Reformation, you're really spoiling us. 

Mango has bee exceptional at turning out these vinyl miniskirts.

These flats also come in red and rose gold. Dreamy. 

Outfit #4: Chic Jeans + Top + Blazer


Christian Vierig/Getty Images

Style Notes: Just want comfort? Fear not; a blazer, tee and jeans can totally work for a first date. Opt for a reclaimed pair of jeans to ensure this look is more exciting.

You probably already have one of these in your wardrobe. 

You'll feel super comfortable in this tee.

These cropped jeans are just what you need for a cool but comfy date-night look.

Outfit #5: Slip Dress + Converse


Melodie Jeng/Getty Images

Style Notes: Sure, a slip dress is great for holiday but a first date? It might feel like you're trying too hard. However, there's a way to elevate the frock du jour so it's as chic as possible—just add high top Converse and a roll-neck.

Always have one of these in your wardrobe. 

Perfect for layering on top of a jumper or underneath. 

Outfit #6: Leather Jacket + Culottes


 Christian Vierig/Getty Images

Style Notes: Not a dress, skirt or jeans type of person? There's a happy medium—culottes. All you need to do is add a leather jacket. 

Wear for a first date and the office. 

Know this: You will never regret buying a leather jacket. 

Outfit #7: Slouchy Suit


Christian Vierig/Getty Images

Style Notes: In need of an outfit that works for the office and then drinks? A slouchy pyjama-style suit is just what you want.