4 Casual Date Outfit Ideas

Cat’s out of the bag: dating can be weird. Nowadays, we have to wrestle with so many questions before the big day, like who’s supposed to pay (feminism, right?), what’s a cheap date idea that will still impress them, should you go in for the kiss now, and of course, what on earth do you wear? 

This guide isn’t for those times when you have a special anniversary or are treating yourselves to a fancy night out. We all have our go-to fits for those, where we know we look good. These four outfit ideas are for when you want to look cute, but casual, but also kind of hot, but not like you’re trying too hard, but definitely still cute (simple, right?).

#1: Jeans and a Nice Blouse

How often do you text the gals group chat to ask what everyone’s wearing only to get back a half dozen “jeans and a cute top” responses? It’s the little black dress of everyday fashion.

Pants are automatically seen as casual, which gives you the freedom to play around with your top half. Here are some ideas to take your casual jeans look to the next level:

  • Opt for a vibrant print
  • Stay simple and trendy
  • Show off some funky sleeves
  • Go classy with a long-sleeve button-down
  • Get summer with an off-the-shoulder top
  • Try out a flirty look with a low-cut sleeveless blouse.

It doesn’t matter what you choose as long as you feel good. It’s your world, and we’re all just living in it.

Styling tip: If you don’t know the exact vibe of your date locale, outerwear is everything. Worried you’re just a tad overdressed? Throw a multipurpose cardigan in your bag. Think maybe it’s the opposite? Opt for a relaxed or oversized women’s blazer. You can always take it off if it doesn’t match the ambiance.

#2: Babydoll Dress

The name may be a little outdated, but the style certainly isn’t. This flowy, t-shirt-dress-adjacent garment gives you the look of a dress (hello, legs) with the comfort and informality you’re after.

The babydoll dress typically features a cinched waist (to avoid an unflattering paper bag look) and comes in an abundance of summer colors and patterns. If this look isn’t earning you any compliments from your date, rest assured it’s a them problem.

Styling tip: This style is one of the absolute easiest to dress up or down. Add a cute wedge sandal for something a little fancier, or a stylish sneaker, like women’s lace up shoes, if you’re going for a laid-back look.

#3: Patterned Midi Skirt and Crop Top

A bold print plus a neutral staple piece, like a cropped knit tank, is the perfect way to have a little fun with your look while still keeping the outfit relatively simple. Some casual but stylish patterns include monochromatic floral, vertical stripes, or the increasingly trendy subtle-leopard print.

A high-waisted midi skirt will leave you with just the right amount of midriff for that little touch of flirtiness (me-ow!).

Styling tip: If you need to throw on a jacket for temperature purposes, don’t mess with the look by layering a long cardigan or oversized jean jacket. Instead, preserve the overall silhouette of the outfit by throwing on a cropped leather jacket.

#4: Denim Skirt and Sweater

There’s something about the juxtaposition of a stylish denim mini skirt and a slightly oversized knit sweater that screams, I didn’t even realize I looked this good. It’s the perfect outfit as the seasons begin to turn and the days get chillier (picture yourself in a hay maze or roaming a foggy pumpkin patch), but it can also work for those outdoor summer evening dates.

If you’re in the budget-friendly business, a denim skirt is an easily reusable basic that will become a sure-fire staple of your everyday wardrobe.

Styling tip: Ankle boots will become your best friend, especially if you’re breaking these bad boys out in autumn. To keep warm, you can layer a pair of sheer tights underneath without sacrificing the skirt look altogether.

Look Good, Feel Good

Whether it’s your first date or 100th, these four outfit ideas will make you feel so confident in your look that you won’t give it a second thought all night. Stop worrying about whether you’re over or underdressed and let everyone else concern themselves with how good you look (especially your date).

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