While going on dates is something almost everyone will have no problem looking forward to, the accompanying shenanigans can make you go overboard with anxiety – where to go, what hairstyle to wear, what outfit would fit the occasion, and a concurrent list of what-ifs.

You want to maintain a relaxed aura for a casual date while at least putting some effort into how you’ll look. You also want to keep a fashionable ambiance without looking like you came out for a red-carpet event.

So how do you achieve this?

Keep scrolling for fantastic outfit ideas that will make planning a date more enjoyable and less stressful.

It’s all about Maxis and Midis

Add some color to a daytime date by wearing a strapless or off the shoulder flora maxi or midi dress and wrap up your look with a pair of ankle boots, trainers, heels, or classic flat sandals. You can always wear your sleeveless maxi dresses during cold temperatures by layering up with a cardigan, a coat, or a fall scarf. It’s one piece that can be worn round-the-year and never gets old. Midi skirts are not left out as they can be worn in any season too. With a fitted top or a button-up shirt, a light sweatshirt, or a chunky knit, midi skirts got your back when your date’s waiting and you haven’t figured out what to wear yet.

Blazers can be Casual Too

Away from the board meetings and formal gatherings, blazers are an excellent choice for a casual hangout, especially if they come in more casual fabrics like cotton or flannel. To drop the office-look for a date-night – look, in blazers; pair them with skinny jeans and colorful or graphic-printed tees.

Denim is a Life Saver

A tee tucked in into denim can never go out of fashion. It’s the classic casual hang out ensemble that you can always fall back on. While you may be used to your blue denim only, you can actually go for white, pink, black denim and love it for a casual date. Denim on denim combo is a safe bet if you are unsure of how to style your denim. A long robe dress or an open front kimono jacket over boyfriend jean + a cami paired with strappy heels and some laid-back accessories will give you a soft ritzy look. And your everyday denim jacket can be worn over a bodycon dress with sneakers for a breezy date night.

Turtlenecks are Everything

Turtlenecks are wardrobe essentials and can be dressed up or down to accommodate any desired look. If you want something classier, then drop your tees and go for a turtleneck instead. Keep it casual with solid silhouettes and simple accessories. For a one-piece turtleneck ensemble, rock a short turtleneck dress with boots and a crossbody purse.

That LBD will Turn Heads

Diamonds may be a woman’s best friend, but they are not the only items on the list of a lady’s fashion BFFs. A little black dress is a must-have, and when everything seems to fail, you can always rely on your LBD. You can wear it on sheer tights and with any footwear of your choice. To play down your LBD, – especially if it’s sophisticated – pair it with sneakers or casual sandals and a shoulder bag, and you’ll get a classic casual allure.

Feel Comfy in Wide Leg Pants

The freedom that comes with wearing wide-leg pants is unmatched. Relaxed, comfortable, and a loose silhouette, wide-leg pants can give you a casual but sophisticated feel when styled to suit the occasion. Rock high waist wide-leg pants in neutral colors by pairing with bodysuits or short cropped tops. Complement this look with wedges or platform heels and fashionable jewelry.

How about a Jumpsuit

Jumpsuits (and rompers) are the only all-in-one clothing there is, except, of course, you want to go a’ layering, which is totally acceptable. With just the right twitch to a jumpsuit, you can go from coffee date material to a fashionable runway celeb. So, it can be quite tricky rocking the one-piece ensemble to a casual date, but it is not hard to pull off.

A jumpsuit paired with a jacket or long coat is a casual chic staple ensemble that can be worn to the movies. You may also opt to layer with a tee or a long-sleeved shirt under your jumpsuit. As a rule of thumb, never wear a jumpsuit with excess material at the waistband to prevent you from looking frumpy or losing your waist in the piece.

Mini Skirts are Sexy

You may want to show that you had your legs shaved, *grins*, or just be in the mood to flaunt those toned legs. Whatever the reason, miniskirts are the right choice for you – without going overboard and showing too much skin. Printed, checked, frayed, wrapped, button-down, suede, metallic, or leather, you can’t go wrong with a mini skirt on a casual date. Wear your minis with any top of your choice and pair with boots, heels, or sneakers. Do not forget to accessorize, of course!

Why not your Favorite Dressy Tops

Go for a dressy-casual look with dressy tops. These fashion staples will put you in check, so you do not do too much or do too little. They can be worn over jeans, skirts, shorts, pants, or any other bottoms of your choice. Just go for the right footwear and dope accessories and watch your date complement your style over and over again!


While it is true that you will look absolutely gorgeous in any of these fashion staples, nothing will be sexier if they are worn with confidence. Also, opt for what you feel most comfortable as this will put you more at ease and make you look forward to enjoying your time to the fullest. With that said, we wish you a successful date time out!

What other pieces do you love to wear on a casual date?

Photo by Laura Chouette on Unsplash