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Style Guide: Date Night Outfits For Every Season

Style Guide: Date Night Outfits For Every Season

Like all things, perfecting the art of the date night outfit can only be done through experience and a tip or two from someone who knows. So here are some outfit ideas for date night:

Spring & Summer Date Night Outfits

THE HEAT IS ON. Literally and figuratively. When it gets hot & heavy with burning desire for your person (new flame or old), throw on a saucy outfit that’ll get their hearts racing. Keep it casual or dress it up a bit for each occasion, but most of all keep things interesting!

We love that Spring is so versatile with style options. You can throw on a skirt and not be called crazy ‘cause it’s cold out, or you can throw on a sweater and not die in the high temps. We love that in the spring, you’ve got options–to say the least.

Essential Denim

date night outfits for every season
date night outfits for every season

First date? Second? Casual dates call for casual outfits that you can feel ultra comfy in to calm your nerves a bit in heated situations. We’re talking cute distressed denim with light knits, or casual sundresses dressed down with a denim jacket. Get the pattern here? The trick is, denim gives the ultimate ‘cool girl’ vibes, and we’re totally feelin’ it.

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Hot Casual Date Night Outfits

date night outfits for every season
date night outfits for every season
date night outfits for every season

Denim skirts & shorts are a go-to in warmer months because they’re short, sweet, and easy to throw on and pair with any top. You’ll love the ease of pairing these with all the colors of the rainbow–even the hardest to match tops will probably go with these! For a cute date night look you can wear for evening dive bar dates, summer state fairs, for coffee, or for the movies, denim skirts and shorts will be your savior! Pair with sexy low cut blouses, or even crop tops and tanks in the sweltering months.

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Jeans Girls

Jeans are the essential we’ve all got in our closet. Pop one on if you don’t feel like wearing shorts or skirts that night. Sometimes jeans can hug your curves far better than a pair of shorts or skirt could. Show off that shapely peach in a good pair of jeans! We especially love the jeans & cute top combo for bar dates or meeting for cocktails. If you want to look like you didn’t try hard at all, this is the look.


date night outfits for every season


If it’s a tad chilly out or if you find your top to already be too revealing, opt for a sleek pair of skinny jeans or boyfriend fits for a more relaxed look. This look is perfect for going to museums, strolls downtown, or meeting for coffee. A tip here is to pair a tight top with relaxed fitting jeans or pairing a flowy top with tighter ones; this way, you’ll have a balanced outfit that shows off your best attributes, and makes you look put together!

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“One and Done” Date Night Outfits

date night outfits for every season

If things get too hot, throw on a spring romper or dress if you want to give off that girlish charm. It’s the effortless look that makes you so inviting and alluring. Oh, this? I just threw it on.

A floral shift dress is so Spring/Summer, we absolutely can’t live without it in the warmer months. It’s easy to throw on, and super lightweight so you can stay cool and collected.

We adore soft shades and vivid florals alike when it comes to rompers and dresses–the perfect one & done outfits that will take out the guesswork from outfit planning so you can worry about more important things. We love interesting necklines, details, and silhouettes for these, like an off shoulder look, or a wrap style with sleeves. Whatever flatters your body, go for it! This look is great for looking sweet and put together, so meeting the parents in one of these will make a good impression.

date night outfits for every season

A spring print we can’t live without is stripes. Actually, you can wear this little number any day of the year so you can consider it a capsule piece you can depend on for years to come! In the warmer months, wear it on its own with interesting earrings to complement the simplistic look. In the colder months, wear this with your fave coat or cardigan and over the knee boots. It’s truly so versatile, you can dress it up or down for casual dates, or slightly dressed up ones.

date night outfits for every season

Don’t want to put a whole outfit together? Rompers are a surefire way to make moves without the effort. A romper with a unique neckline shows off a little skin and adds some interest to the piece you’re wearing while showing off your best assets. One that cinches at the waist is flattering on most body types, but go for a shift silhouette if you want to go for something more flowy and loose! Whatever’s comfortable, babes!

date night outfits for every season

For an easy day to night date night outfit choice, wear a romper with deep romantic hues like reds, deep purples, etc. You can wear sandals during the day and pop on some sexy ankle strap heels to take it to night. They’re also super lightweight and keep you cool. You’ll definitely stand out in the crowd in one of these babies. The wrap style boasts a flattering v-neckline, and accentuates the waist in one go. Shine on, ladies!

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Special Occasion Date Night Outfits

date night outfits for every season

If your date suggests something a little more upscale than the usual picnic or movie date for date night, you’re gonna need a sleek and elegant ensemble to set the mood. Revive the little black dress you have in your closet and take your pick. When shopping for a date night dress, look for something that is understated and classic so that you can wear it for years to come (that’s a capsule wardrobe tip we all know and love). Something like a strapless mini is always in season. If a bodycon isn’t your thing, go for a slip dress with lace detailing that accentuates the body and keeps things interesting. It’s loose but still sexy.

date night outfits for every season

Don’t forget accessories. Pair your dressy look with understated and sophisticated heels and a light coat or leather jacket, complementing the outfit but not being too overbearing.

Getting all dressed up to go out and being in love, are two things most of us can agree are a pretty good time. Getting dressed up to go out because you’re in love can be even better, especially when you’ve mastered the date night outfit to the extent of being able to look your flirty and fashionable best at a moments notice; remaining open to spontaneity and looking amazing while you’re doing it.

Fall First Date Outfits

The best thing about a first date is the thrill of potentially finding a long-term S.O. Most often, these dates are super casual, so you don’t want it to seem like you’re trying too hard. Pair classic basics with chic pieces to elevate an otherwise simple everyday outfit. A sweater dress is the perfect go-to when it comes to merging casual with slightly dressy. Try a romantic hue like a wine colored knit dress, and pair with your fave ankle booties. You can even opt for sneakers to dress it down!


We’re also really into a comfy flannel and short combo for a casual date–you can never have too many flannels! Plus, they’re super versatile and the ultimate laid-back cool-girl piece to have in your collection.

Casual Winter Tops


  1. Dinner Date Outfit

    This can mean a lot of things so keeping it simple and chic goes a long way. Flirty basics like slip dresses, which are back in all of their 90’s glory, in a wine or deep olive color, can make for great staple pieces for the fall; looking back a little, something in a blush could be great for when the weather feels a little warmer.

    Add a little attitude to a very feminine dress style with something classically chaotic, like a slightly oversized camo jacket. It’s the sort of outerwear that can go from optional to essential like that. Show you’re date that you’re totally comfortable in your own skin by being bold—mix it up on your night out. We also love statement outerwear like this with classic skinny jeans and a simple blouse.

    Let the accessories set the tone from there; throw on your favorite necklace, earrings, or rings to kick it up a notch.

    Dinner Date Outfits

    Happy Hour or Bar Hopping Outfit

    For happy hour or bar hopping, you definitely want to keep that laid back vibe in your outfits. Especially if you’re going to be dancing and drink, you probably want to be comfortable, but still want your personality to shine through. A blouse and trusty black jeans that are appropriate for the office can also be perfect for happy hour or drinks after. With a quick switch of your shoes and accessories, you can be bar-ready!


    Gallery hopping or Museum Date Outfit

    If you’re doing this right, it usually means hitting a bar or club once you’ve passed through each show, so fashion and function are important because long hours of lots of moving around is what it all comes down to, and you want to be cute and comfortable. A dress is perfect for this occasion since you can wear it dressed down or styled up! The right dress with heels that you look great and feel good in, creates a romantic look that can be dramatized or sweetened with the help of strategic makeup choices. Emphasize your artsy side with a fashion-forward piece with eye-catching patterns and/or colors!

    A date in the great outdoors

    Maybe you’re going somewhere like the Hi Line in New York, a modern park in the middle of a big city, maybe you’ll take a hike or do something totally random like visit a botanical garden, whatever the case, denim is the answer; as it so often is. Pairing a casual pair of boyfriend jeans with a top that comes across high fashion and fun will always be a winning look, and ankle booties or slip on sneakers with a slight platform are all you need to perfect that vibe.

    Concert date

    There’s basically a uniform that exists for concerts, and there’s really no need to stray too far from what has been established. Wear your best jeans, maybe a leather skirt, and a simple T-shirt, and update outfits like this with stylish embellished denim outerwear which seems instantly timeless in the height of its trendiness. Embrace and then mix up the double denim look with denim heels or booties in a contrasting wash and you’re good to go!

    Formal Date

    Formal dates are inevitable in any relationship. Whether you’re a plus one for a company party, or someone’s wedding date, be ready for what’s to come! In these cases, you’ll want to make a good impression on more than just your date. Dresses veering on the more classy & conservative realm do a great job of doing just that. Find out what silhouette works for your body type, your color of choice, and don your favorite dressy heels & earrings.

    Meet the parents

    Meeting the family or friends of your special someone (they’re probably pretty special if you care about meeting their parents or friends) is a big event, and it could be said that the type of outfit you style for something like this could be a blueprint for any commemorative dates going further; like holidays and birthdays. As a matter of fact, that’s exactly what’s being said here and now. A blouse is the way to go when you want to look put together. Pair with your fave pair of denim or black jeans, and you’re ready in a pinch!

Whatever you’ve got planned for date night, let these outfit ideas be the spark. Get your creative juices going, and get in front of a mirror. You’re expressing yourself as much as you’re making an impression, and that’s the best part.