What to Wear on a Casual Date


Casual dates are the hardest kind of date to dress for. Do you debate whether your outfit is too fancy or too casual when you’re just going out for mini-golf or a movie? Does a T-shirt count as casual, or will that just look sloppy in comparison to your date’s outfit? The stress is real. 

To help you out, here are five solid outfit ideas that are a perfect blend of comfort and fashion. You’ll feel great in them, but you won’t have to worry about being over or underdressed.  

What to wear on a casual date

Shop this look: Lisa Blue & Olive Midi Jumpsuit

Casual Date Styling Tips

Soft Jumpsuit With Low Wedges  

No matter what kind of date you’re going on, a jumpsuit will do the trick. That’s why they’re such a versatile buy! Pull on your comfiest one and voila, your entire outfit is complete. Jumpsuits look especially flattering when paired with a little bit of a heel, so slip into some wedges that give you just a tiny bit of extra height. Make sure the wedges aren’t too tall though or you’ll slip from the semi-casual category straight into runaway material. 

Skinny Jeans Under a Flowy Top 

Jeans are a surefire way to keep an outfit from looking too dressy, and they’re always easy to match things with. Shrug into your favorite pair, then dawn a flowy but flattering top. Try to pick one that is nice enough to wear during an evening out but not so fancy that it clashes with your casual jeans. Pair the look with some low booties or flats, then you’re ready to head out the door. 

casual date

Shop this look: Michelle Blue Floral Choker Romper

Floral Romper and Some Sandals 

If it’s warm enough outside, rompers are a great way to show some leg without resorting to your favorite pair of jean shorts, especially a flirty floral romper. They’re equal parts girly and practical, so you can feel comfortable knowing that you can handle whatever kind of activities your date has planned. Keep the whole look low-key by stepping into simple black or tan leather sandals.

T-Shirt Dress With Sneakers 

Dresses are often risky when it comes to keeping things casual, but if you select the right style, you should be fine. T-shirt dresses are (a) comfortable enough to lounge around in and (b) cute enough to rock in front of your crush. Add a trendy jacket and your favorite fashion sneakers for a look that is as effortless as it is adorable. If you’re worried that you can’t pull off a shapeless T-shirt dress, give it a little shape with a slim black belt. This will show off your waist and keep you from looking too frumpy. 

Denim Skirt and Striped Shirt 

Who says denim has to be blue? Black, brown, and millennial pink denim skirts are all the rage right now. Pick the color that looks best on you, the tuck a matching striped shirt into it. Not only will you look totally put-together, but you’ll also look casual enough to head on any kind of outing. White tennis shoes or brown booties are a great footwear choice, and if it’s chilly outside, pair the outfit with a sleek bomber jacket. 

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