Written by Claire Jensen (ASI Head of Training & Development)
Date night. Two words that have the power to make even the most confident of us second-guess everything in our wardrobe. Whether it’s the butterflies of a first date or the comfort of date night with your long-time love, choosing what to wear can feel like a high-stakes game.
I’ve always found second dates more nerve-wracking than firsts. Hear me out. By the second date, you’re already a little invested. You liked them enough to see them again, and now you’re hoping they still like you when the small talk is out of the way and you’re diving a little deeper.
And with Valentine’s Day around the corner, you may have a date planned with someone you’re invested in and are wanting to take things further. But then there’s that age old question: What will I wear?
For me, for any event I attend, especially a date, my outfit choice is my secret weapon. If I dress in a way that makes me feel confident, vulnerable, and (let’s be honest) a little sexy, I could relax and focus on just being myself.
Here’s the thing: first impressions are formed in as little as 1.5 seconds. Yep, before you’ve even had a chance to tell them your name, they’ve already made judgments based on what they see. Human Behaviour research tells us that we gather information about someone through three key areas:
- Behaviourally – how you act and carry yourself.
- Linguistically – the words you choose and how you say them (though this accounts for only a small percentage of the impression).
- Physiologically – how you present yourself visually, including your clothing, grooming, and body language.
Given that 40% of people are highly visual, your outfit speaks volumes before you even open your mouth. Let’s make sure it’s saying the right things! Here are my top five tips for date night dressing that work for first dates, second dates, or even that weekly ritual with your partner of 10 years.
1. Dress to Feel Like Your Most Confident Self
Confidence is attractive, plain and simple. The key to dressing for confidence is knowing what makes you feel good. Whether it’s a tailored blazer, your favorite pair of jeans, or a little black dress that hugs all the right places, choose pieces that make you walk a little taller. Remember, confidence isn’t just about looking good – it’s about feeling like the best version of yourself.
2. Dress for the Date Activity
What you wear to go for coffee and a walk is going to look very different from what you’d wear to dinner and drinks. Think about practicality and comfort. For an active date, opt for stylish yet comfortable sneakers, a great pair of jeans, and a top that gives that effortless vibe. For dinner or a gig, step it up with tailored trousers, a top with more personality like a printed tee or shirt, and a blazer or leather jacket. Dressing for the activity shows you’ve put thought into the occasion.
3. Make an Effort
Your outfit doesn’t need to scream “I’ve spent hours getting ready” (unless you want it to!), but it should show that you’ve made an effort. Investing in your appearance sends a subtle message: “I value myself, and I’ll value you too.” Self-care, from your grooming to your outfit, tells people a lot about your character.
4. Footwear Matters
In my professional opinion, Crocs are not date night appropriate. Shoes can make or break an outfit. Whether it’s sleek ankle boots, polished loafers, or strappy heels, your footwear should complement your look and be appropriate for the activity. Bonus points if they’re also comfortable because nothing kills a vibe faster than aching feet.
5. Express Yourself
Your style is a reflection of your personality, so let it shine! If you love bright colors, bold prints, or accessorizing with vintage brooches, don’t shy away from incorporating these into your date night look. It’s a way to communicate who you are, not to mention will allow you to show up as your most authentic self. Remember, someone worth dating will appreciate that.
Date night dressing doesn’t have to be stressful. The secret is to balance effort, practicality, and self-expression. When you feel good in what you’re wearing, it shows – and that’s what really leaves a lasting impression.
So, the next time you’re staring at your wardrobe in panic, remember this: dress for confidence, dress for the occasion, and most importantly, dress to be you. Because if they don’t like you after that date, it’s their loss – and at least you’ll look fabulous walking away.
Happy styling!
Claire
