How To Choose an Outfit for a First Date

If you don’t know what to wear on a first date, you’re not alone.

Finding the perfect fit can be overwhelming when the stakes are high, and your appearance can be a decisive factor in whether a first date results in a second…

👔 Ready to choose the right an outfit for a first date?

I’ve shared the 5 most important tips you need to know below 👇

HOW TO CHOOSE AN OUTFIT FOR A FIRST DATE TIP #1:

Make Sure Your Outfit Fits

The #1 fashion mistake men make (not just when choosing an outfit for a first date!) is wearing clothes that don’t fit.

In general, women are forgiving about men’s fashion:

• Women rarely seek out guys with specific stylistic choices…

• Women tend to be more forgiving of mens’ appearances than men are of women’s generally…

But no matter what you’re wearing, if it’s too big or too small, you can kiss a second date goodbye 😬

Ill fitting clothing is distracting, and indicates you either have terrible style, or you don’t care enough about your date to dress nicely. Neither is a message you want to send!

Unsure if your clothes fit?

Check out this fit cheat sheet from master men’s stylist (and my friend!) Peter Nguyen.

Here’s a quick rule of thumb though:

If you worry your clothes are too tight or too baggy…

Your clothes are probably too tight or too baggy.

🧵🪡 Fortunately, the problem is easy to fix with a good tailor.

Don’t be afraid to not work with the first tailor you talk to. It’s important you find someone you communicate well with!

HOW TO CHOOSE AN OUTFIT FOR A FIRST DATE TIP #2:

‘Where’ Determines What You Wear

Like with choosing a property, when you’re choosing an outfit for a first date, a key consideration is “location, location, location.”

If you’re under or overdressed based on where you’re headed, you’ll look like a clown. And women don’t exactly like clowns 🤡

• I’m rarely enthusiastic fancy first dates (your goal is to create an interpersonal connection, not impress your date) but if you’re headed somewhere swanky, you shouldn’t be in shorts or sandals at the least…

• Likewise, if you’re headed to a dive bar, you’re going to look like an idiot if you’re wearing a tie (and she won’t be excited that you “rushed from the office…”)

If you’re not sure what to wear, look up your date venue on Instagram, and let the outfits the guys are wearing in the most popular posts be your guide 📍

(Btw if you need date idea inspiration, check out some of my favorite first date ideas here!)

HOW TO CHOOSE AN OUTFIT FOR A FIRST DATE TIP #3:

Mind the Details

Let’s be honest. She probably won’t care whether your shirt is white versus yellow, or whether boots versus loafers adorn your feet 👞

However, she absolutely notices and cares about details that signal how much you respect her, and well you take care of yourself like:

• Is your shirt ironed and crispy? Or is it wrinkled?

• Are your jeans clean? Or is there a nasty stain from the burger you ate for lunch?

• Do your clothes look cared for? Or are they badly faded, and covered in lint and fabric pills?

Get these details right if you want to look good for your date!

HOW TO CHOOSE AN OUTFIT FOR A FIRST DATE TIP #4:

Minimize Risks

First dates come with enough uncertainties — don’t let your outfit add to the list.

If you’re debating between two outfits (or you’re unsure what to wear generally) opt for the simpler and safer choice.

Why?

• If you’re sharply dressed, she’ll appreciate it, but your outfit won’t meaningfully impact whether she wants a second date. On the other hand, if you dress badly, it will absolutely roast your chances of a second date.

• First dates aren’t fashion shows. She’s there to get to know you, not be wowed by your dazzling dressing skills.

• At the end of the day, the best first date outfit is the outfit you feel the most comfortable in!

HOW TO CHOOSE AN OUTFIT FOR A FIRST DATE TIP #5:

Follow These Do’s And Don’ts

I’m hesitant to give specific tips, and style is personal anyway…

But if you’re really at a loss for what to wear on a first date, it’s hard to go wrong with a nice-but-neutral outfit like:

• White button-down shirt (either short or long-sleeve)

• Straight-legged jeans (not too skinny, not too loose)

• Classic tennis shoes (like Chuck Taylors) or dress shoes (like loafers)

Likewise, no matter what, avoid:

• Open-toed shoes (unless you’re going to the beach)

• Hoodies (you’ll look too casual)

• Ties (you’ll look too formal)

• Busy patterns (they’re too distracting)

Otherwise, focus on outfits that make you happy, and accentuate your personal style.

And remember to not wear flip-flops 👇❌

HOW TO CHOOSE AN OUTFIT FOR A FIRST DATE

Closing Thoughts

First impressions matter, and choosing the right outfit for a first date can help you make a great first impression.

The most important things to remember are:

1. Make sure your clothes fit 🧵🪡

2. Consider the location of your date when choosing your outfit 📍

3. Mind the details ✨

4. Minimize risks ⚠️

5. Follow my do’s and don’ts ☑️

One last tip: remember that you wear the clothes, and don’t let the clothes wear you 😉

Also, if you want more first date pointers, check out my post on if you should kiss on a first date here, and when to text her after your first date here!

PS. Ready to uplevel your dating life fast?

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• 📲 What I Swipe Right On (how to improve your matches on apps like Hinge fast)
• 💬 Master The Message (how to create more chemistry via text)
• 🏀 How To Bounce Back (dating 101 for newly single guys)
• 😅 You're Nice, But... (dating 101 for "nice" guys)

Just pop in your name and email below, and I'll send over your free guides immediately!

Xo Blaine