Deciding what to wear on a first date is just one of the many small anxieties that arise when seeing someone new. Where are we meeting? Will the conversation flow? Are they a serial killer?

But! Let’s focus on something you definitely can control: your outfit. Once you figure out what to wear on a first date, you may find the rest falls into place. Because the right look isn’t just about looking good — it’s about feeling like the absolute best version of yourself.

Below, some favourite tips and outfit inspiration for what to wear on a first date this autumn and winter 2025.

1. Dress for the Actual Date, Not Just the ’Fit Check

We get it — there will always be a temptation to dress like you’re walking a runway for any occasion where you want to make a good first impression. But nothing kills a vibe faster than being overdressed outside a London pud — or underdressed at a swanky rooftop, for that matter. So, think about the setting and dress accordingly.

A coffee date? Keep it casual with a cute top and a well-fitted pair of jeans. A fancy dinner? A sleek midi-skirt and blouse or a little black dress with high heels does the trick. A museum date? Go for an oversized blazer over a button-down shirt or a wide-leg jumpsuit that strikes the perfect balance. Consider it style game theory: Match the moment without losing yourself in the process.

Tchesmeni Leonard, the senior fashion editor at Glamour US, agrees: “First dates can be thrilling but nerve-racking, so I always aim to wear outfits that make me feel confident while keeping comfort in mind.” Her go-to? A well-fitted pair of straight-leg jeans with a simple tee or tank and her favourite heels—usually a pump or strappy sandal.

If the date calls for something a little more elevated, Leonard likes a midi-length slip dress layered under a cropped cardigan or leather jacket with boots or heels, depending on the season. Her best advice? “Start with a fabric that feels good on your skin, then pick a fit or silhouette that makes you feel like your most confident self.”

Edward Berthelot/Getty Images

Jeremy Moeller/Getty Images

2. Comfort Is a Nonnegotiable

The cutest outfit in the world means nothing if you’re fidgeting, pulling, sweating, shivering, or losing circulation in too-tight jeans. If you’re constantly adjusting your top or limping from painful shoes, you’re going to be more focused on your suffering than your date. Whether it’s a cardigan layered over a T-shirt for a casual cocktail, or dark jeans with a tucked-in button-down and a great pair of earrings for a dinner date, wear something you can forget about.

And whatever you do, avoid the regret ’fit — you know the one. The shirt that starts out fine but rides up as the night goes on. The shoes that feel fine at home but pinch 30 minutes in. The unfamiliar trend you convinced yourself you could pull off but secretly think looks ridiculous. First dates come with enough unknowns — your outfit shouldn’t be one of them. If you’ve never worn it before, don’t let this be the test run. Stick to a go-to date-night outfit you know works.

Edward Berthelot/Getty Images

Edward Berthelot/Getty Images

3. Favour Personal Style Over Trends

This is not the time to debut an experimental new look that you don’t actually love. The goal isn’t to impress them — it’s to express you. If you’re a minimalist, lean into clean lines and great tailoring. If you love bold choices, go ahead and rock that minidress with statement jewellery. Let your outfit introduce you before you even say hello.

Edward Berthelot/Getty Images

Edward Berthelot/Getty Images

4. Find a “Subtle Power Move” Piece

Find one thing — just one — that makes you feel unstoppable. It could be a killer leather jacket, a powerhouse blazer, a pair of earrings that makes you feel like an It girl, or a perfectly broken-in vintage tee. Maybe it’s a denim jacket thrown over a long-sleeve maxidress, or a miniskirt with an interesting hem. This is your signature. Your “main character energy” item that gives you a silent confidence boost.

Edward Berthelot/Getty Images

Edward Berthelot/Getty Images

5. Keep Your Beauty Look Groomed but Effortless

For your makeup and hair, think polished, but not robotic. A little hair tousle, a little glow, and a look that says, “I woke up like this” (even if you certainly did not). I am obsessed with Rimmel London’s Thrill Seeker mascara in Cappuccino right now – I have been loving brown mascara for that slightly more natural take on fluttery lashes.

Matilde Bono/Getty Images

Matilde Bono/Getty Images

6. Do a Vibe Test Before You Go

Before you walk out the door, ask yourself: Does this feel like me? Would I want to run into someone from high school wearing this? Am I comfortable enough to actually enjoy the date? If the answers are all yes, you’re golden. If not, tweak until you feel effortlessly yourself. Because at the end of the day, the best outfit is the one that lets you focus on what actually matters: having a great time. Or at least, a good story.