Where my single ladies at?! Dating can be a lot of fun, especially when the weather begins to warm up. Despite the spring sunshine, figuring out the perfect first date outfit can be quite the challenge. You can only make the all-important first impression once, so you want your outfit to be just right. I have a few go-to outfits that make getting ready a snap, so today I’m sharing my best tips for the perfect first date outfit.

1. Keep it comfortable. This generally means don’t wear anything too constricting, ill-fitting, tight, or complicated. On a first date you want to project confidence more than anything else, and you can’t show that off if you spend the entire time tugging on your hem or adjusting your top.  Also, don’t leave the house before doing the at-home sit test. Your outfit should be comfortable no matter what comes up.

2. Wear your old favorites, and stay away from new clothes. I find it’s best to wear my favorite pieces that I always feel good in. I add new clothes to the list of things to avoid, only because you don’t yet know how they feel after a few hours of wear, and a first date isn’t exactly the best place to find out. Remember, your date has never seen any of your outfits (beyond your dating profile) so anything you choose will be new to him or her even if it isn’t new to you.

3. Dress for the occasion. Hopefully it goes without saying, but carefully consider the activity when selecting your outfit. If you’re going for a casual Sunday brunch make sure to wear something carefree and easy and not too formal. Going for a coffee and a walk through the park? Make sure to wear comfortable flats instead of your favorite first date pumps. Pay attention to the weather, too! Although I usually err on the side of overdressed, I only wear pumps like these when I know limited walking will be involved.

4. Accentuate the positive. Since this is a date, it’s all about attraction. We are all hardest on ourselves when it comes to appearance, so plan your outfit around the features that make you feel the best about yourself. For me, I like to go with something that accentuates my waist and shows off my legs like this tee tucked into my favorite skirt. If the weather calls for pants, I usually opt for an open neckline and tuck my top into my belt. No matter what I choose, I know I’ll feel best if I plan an outfit around the features that make me feel amazing.

5. Go light on the accessories. Don’t get me wrong, I love accessories. But on a first date, piling on jewelry, scarves, hats, and more can be overdone, jangly, and distracting from your natural beauty. I think it’s good to pick one great accessory, like one great necklace or one great shoe, and focus on that. I also like to carry a small handbag on a date since a big bag can be too cumbersome and may appear high maintenance. When in doubt, apply the thoughtful advice from the godmother of personal style, Coco Chanel, who famously said “Once you’ve dressed, and before you leave the house, look in the mirror and take at least one thing off.

6. Appear effortless. Effortless means different things to different people. To me, it means looking like you’re not trying too hard. I always want my first date outfits (and most outfits really) to have a dressy yet casual vibe that looks like I just threw something on before leaving the house. That’s why I prefer pieces that don’t perfectly match but rather coordinate. That’s why I often incorporate t-shirts and jeans with holes in the knees, because it not only exudes confidence, but shows that I’m not too fussy about what I wear.

Outfit Details

top, | skirt, Banana Republic | pumps, Ted Baker London | crossbody bag, Rebecca Minkoff | watch, Apple Watch Series 1 in rose gold | rings, a mix of Madewell, World Market, and Red Envelope | blazer (held), Banana Republic thrifted at Goodwill

Get the Look

I think skirts are one of the best things to wear on a first date, so I’m thrilled to be partnering with Michelle of Michelle’s Pa(i)ge and Ana Luiza of Northwest Blonde for their spring skirts link-up today! Share your favorite skirt outfit post and check out the amazing outfit ideas from other stylish bloggers.


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