Best First Date Outfit Ideas for Men: From Casual to Sharp
If scoring the date is the most nerve-racking thing, then figuring out what to wear on a date has to come in as a close second.
And by the way… those jitters you’re feeling? They’re a good thing! It shows you actually care and want to make an effort.
Believe me, that in and of itself puts you light years ahead of 99% of the guys out there. I’ve been with my hubs for six years but am still suffering from PTSD from some of the first date outfits I got exposed to as a single gal (don’t even get me started on the pickup lines).
But before we show you some date outfits for men that run the gamut from casual to sharp, there are a few key pointers to think about first.
Be Yourself on a First Date… To a Point
Patrick and I can both attest to the following declaration that a lot of guys make: “I’m going to wear flip flops on my dinner date because I want to be myself.” Well… Good luck with that. Don’t get me wrong, being yourself is a great asset, but your clothes are going to speak volumes.
Believe me, the gal you’re about to meet up with has most likely spent an enormous amount of time figuring out what to wear, how to style her hair, and debating the merits of kiss-proof lipstick (optimism) or a sticky gloss (strictly insurance… most men hate this stuff, so we know you probably won’t try to kiss us if we’re wearing it). Point being: make an effort with your outfit. It says a lot. And honestly, it means a lot to us, too. You’re basically telling us, “I think you’re worth it.”
But there are other fringe benefits of dressing well for your date:
Women assign much deeper meaning to many random things, including your outfit. If you show up in your wrinkled shirt and flip flops, we will make a split second, iron clad judgement that you are most likely going to be sleeping in when you should be going to work, eating Lucky Charms for dinner, and still living in your parents basement. In other words: pass.
You’ll get treated better… by everyone around you. Studies have shown that when people perceive power, they respond with respect and assume you have status. Plus, when men can walk into a room and just naturally command attention and respect simply by the way they carry themselves, it’s a turn on for us.
Mentally, you’ll get in the zone faster. Enclothed Cognition has proved that what we wear has a direct effect on how we perform. If you are what you eat, then you most certainly are what you wear. It’s why those top surgeons don white lab coats, not ripped jeans.
But also keep in mind some words of wisdom from Patrick:
“Being the guy in a suit at a sports bar draws the wrong kind of attention. it looks ‘try hard’. Worse than that, it can signal to your date that you’re a bit desperate since you need to work so hard to impress her.”
He’s right. There’s a sweet spot to figuring out what to wear on a date. Not a tuxedo, not your flip flops, somewhere in between, but just a notch above everyone else. The goal is to stand apart, not stand out like a sore thumb.
So, here’s what you can wear on a date the next time you’re heading out to meet your new favorite person. When choosing your look, also consider the venue, the time of day/night, and what feels most like you.
BEST FIRST DATE OUTFITS FOR GUYS
Best first date Outfit For Guys no. 1: Casually Pulled Together
Dark denim just naturally skews more elevated than something with a lighter rinse, even when it’s worn casually. Add a white cotton henley and a lightweight suede trucker jacket that you keep on as part of your outfit, rather than taking off as soon as you step inside, and keep it unbuttoned for a low key vibe. Finish this one off with a pair of slightly faded looking leather boots and a matching belt.
Shown: AG Jeans, Todd Snyder, FRYE, Thursday Boot Company (boots + belt)
BEST first date Outfit FOR GUYS no. 2:
Elevated Casual
Again, thinking of how we can elevate something as simple as denim, stick with darker rinses: black, indigo, charcoal gray. An alternative would be a five pocket pant in rich navy, gray or black. From there, you can layer on something as simple as a crisp white or black t-shirt followed by a quarter zip sweater made from cotton, merino wool or even cashmere. Step into a grey or black suede sneaker and you’re out the door.
Shown: Bonobos, Son of a Tailor, Suit Supply, Zegna
BEST first date Outfit FOR GUYS no. 3:
Dressy Sharp
A lot of women love wearing blazers… especially oversized ones. Top it off with the ever-so-slight scent of cologne being worn by someone we’re into and oh my. Melting. Are you catching my drift? There is something irresistible about the idea of draping your blazer over our shoulders as the evening chill sets in (or when we fake being cold). You look chivalrous and we feel closer to you. So, for this one, you can’t go wrong with a casual blazer, five-pocket pants, a long sleeve polo and a chic pair of black leather Chelsea boots. And by the way, if you need some pointers, Patrick covers all the bases in this video about how to choose and wear cologne.
Shown: Proper Cloth, Robert Barakett, Faherty, RM Williams
BEST first date OutfitS FOR GUYS:
Elements of Masculinity
Talk about the ultimate “accessory” for your outfit. Whether your style vibe is preppy, classic, rugged, rock, street, rakish or whatever, any date outfit for men should 1000% incorporate some elements of masculinity. No cartoon socks. No smiley face t-shirt. You’d be surprised how much these pop up on date night. Sigh. As Bonnie Tyler lamented in her smash hit and Footloose anthem, Holding Out for a Hero, “Where have all the good men gone? And where are all the gods?”
We want a man who yes, has a heart of gold, but we REALLY want a man who looks and acts like a man. Things like leather, suede, denim and boots just inherently make you seem more manly. In other words, always go for the argyle socks over the French fry socks.
And remember, you don’t need to go ham and put together an outfit that incorporates every one of these elements. Just one or two is totally fine. We’ll get the message.
Okay, fellas, there you have it. We hope you found this one useful when it comes to what to wear on a date, feel confident wearing your outfit and have a great time!
HOW TO Take Your Style to the Next Level
If you want to take it a step further and enlist the aid of a professional image consultant to help you develop a signature style and look that’s uniquely you, we’re here to help in a number of ways:
1. We have a load of free style resources we put out here that you can use to begin to elevate your style and image right now.
2. Our in-person personal styling service where you’ll spend a full day with our founder, Patrick, 1-on-1 to talk about your personal image goals, learn what colors look best on you, get haircare/skincare/grooming tips, get your wardrobe squared away and personal branding in check. This package includes tailoring, sorting/editing your existing stuff, and shopping for all new pieces that fit you, your style, and your budget.
3. Our online personal styling package where you’ll work with our whole team to get yourself a new overall image. We’ll meet with you 1-on-1 virtually to show you what looks best on you and why, hairstyle/grooming/skincare tips specifically tailored to you, color theory training, fit training, a complete shopping list of new items, and style support for 6 weeks as you implement everything.
4. If you’re unsure what option works best for you, you can schedule a quick call with Patrick, right here. It’s complementary and he can definitely help give you some direction.
Cheers!
Kate
