Style - February 13, 2019

What To Wear On a First Date

Hi friends! Remember weeks ago when I mentioned I was putting together a post on What to Wear on a First Date? Welp, 3 weeks later it’s finally here ;) Honestly, when I went to pick out an outfit for this post, I got kind of stuck. Which is fitting I guess because I know we’ve all been there trying to pick out the *perfect* first date outfit, texting our friends, trying 50 things on, and second guessing everything.

What I realized after going through a few options was that 1. Basics were best and 2. I know I didn’t want to feel over the top. Like I’m a jeans kind of girl, so why would I even consider wearing a skirt or something just because it’s the first date? So with that, here are a few things to keep in mind…

Consider the weather and location

Before your mind goes directly to an outfit, be rational. You don’t want to be that person who shows up in a ridiculously over-styled outfit or something that doesn’t fit the weather. At least for me, because that’s not who I am in real life, I wouldn’t want to portray that ya know?

A bar or local tap room or something obviously calls for something pretty casual and I wouldn’t wear anything higher than a heeled bootie. If you’re meeting for coffee or something even more relaxed, consider a cute pair of slides that still make you feel styled but without being overdone and feeling kinda ridic. Really the only time I’d consider a dress or heels is if the first date was a cocktail event, which probably isn’t the case…

Start with a favorite piece piece

Find that one piece that makes you feel FREAKING AMAZING when wearing it. Those jeans that make your booty look cute (y’all know the ones), or for me, a pair that actually make my legs look longer than they are, or the ones that aren’t so tight you can’t sit down in. Or maybe it’s a shirt that’s flattering and versatile or even a pair of booties that you feel like YOU in.

I picked these Ankle Button Black Jean because they’re soooo comfy AND I like that they add length to my frame (especially when I do a messy front tuck because the buttons and the extra high waist fabric make my legs look longer).

Got that item? Ok now…

Pair it with other basics

In my opinion, the first date isn’t the time to wear some crazy trend or something that will noticeably make you feel uncomfortable. (That’s more girl cute, which is fun for girl’s night.) I’m pretty sure first dates can be awkward enough – you want to wear what you’re comfortable in. For me, that’s basics, and I don’t think anyone can go wrong with them.

I’ve always thought of a button-down blouse that is NOT stiff is one of the most universally flattering and versatile pieces. It’s a staple in my closet, date or no date, but it works well for the first date. You can play with the buttons and how much skin you want to show, but it still feels classy yet relaxed right? Right. I rolled up the sleeves on this Topshop pocket shirt ($55) to make things feel even more relaxed.

Don’t go crazy on shoes

We touched on this earlier, but one of my main tips for a first date is to WEAR SHOES YOU CAN WALK IN.  Seriously! Walk in them for a while at your house before wearing them to make sure they’re comfy enough and don’t kill your feet or the night.

For me, that’s going to be a cute pair of block booties like these that I’m obsessed with, wedges, a pair of slides, or heck, even sneakers if the date was really casual.


If your outfit feels basic and you’re wanting something snazzy to add to it, do that with your accessories! A fun pair of earrings or your favorite bag can show some personality without doing too much with the outfit. Personally, with this outfit, I liked wearing my basic jewelry to keep with the relaxed/Brighton theme, but a fun earring could have been cute, too!

Look like you

In the same vein, when it comes to hair and makeup, I’m going to say the same thing: look like you. Sure, y’all might want to wear a little extra mascara or to get a blowout and that’s fine! We want to feel our best! But I wouldn’t go for a heavy red lip or some overdone curl situation if that’s not you. Pretty sure most guys apprecaite meeting the real you anyways :)

I’ll put some other ‘First Date Outfit Options’ right here in case Y’all want more to choose from and you can see all my outfit details below!

Outfit Details