With fall’s milder days, date nights call for outfits that embody a perfect blend of laid back comfort and a hint of structure.
I’m looking forward to some upcoming events, whether it’s a casual dinner or a bonfire with friends, and find it’s always handy to have some outfits in mind that feel effortlessly styled.
Today I’m sharing some of my go to date night outfits for the season. Let’s take a look at some of my top picks.
1. Overalls and a Turtleneck
Overalls are making a huge comeback, and I am so here for this trend! For a fun retro vibe on your date night, try pairing them with a long sleeve turtleneck.
You can finish the look with either ankle boots or some classic white sneakers. A baker boy hat adds such a playful touch to the whole ensemble.
2. Mini Skirt, Tall Boots, and Sweater
A ladylike mini skirt paired with over the knee boots is such a killer combination. I love this look because it works for daytime and nighttime plans.
To balance everything out, just throw on an oversized knit sweater on top. It’s a total winner.
3. Jumpsuit and Heels
A jumpsuit is one of those chic one piece options that I find myself reaching for again and again. It moves so easily from a day look to a night out.
For an effortless evening vibe, match a dressy jumpsuit with strappy or block heels and some simple jewelry. A leather jacket is the perfect piece to give it an extra boost.
4. LBD and Statement Heels
You seriously can never go wrong with a little black dress; its timeless versatility is everything.
To really make this cocktail dress pop, go for some statement heels in a vibrant color and add a box clutch.
5. Sweater, Jeans, and Mules
I love this outfit combination because it’s just so comfy and cute. A roomy knit sweater with jeans or leggings gives off such a relaxed vibe.
You can easily dress it up by slipping on some mules that have a little bit of a heel.
6. Faux Leather Skirt, Mock Neck Top, and Booties
An A line faux leather skirt gives your outfit some great structure, while a mock neck top keeps things looking sleek.
Just add your favorite booties and some dainty gold jewelry to tie the whole look together.
7. Plaid Button-Up and Jeans
This is such a classic fall combo that you really can’t beat. Pairing a plaid flannel with jeans or leggings is a must have for the season.
I like to roll up the sleeves and finish the look off with some cross strap shoes.
8. Wrap Maxi Dress and Strappy Heels
A wrap style maxi dress is universally flattering because of the way it cinches at the waist.
For a date night look that is both comfortable and elegant, pair it with strappy heels and a moto jacket.
9. Sequin Dress and Heels
I mean, nothing says glamour quite like a sequin dress! Choose a style with a midi or maxi length in a jewel tone or metallic color.
For a look that’s totally red carpet worthy, just add strappy heels and some dazzling jewelry.
10. Corduroy Pants and a Cropped Sweater
Corduroy pants are an absolute fall wardrobe staple. If you’re planning a date night, pair some high waisted cords with a cropped sweater.
To complete this of the moment look, throw on some ankle booties.
11. Sweatshirt, Leggings, and White Sneakers
Keeping it super casual? A graphic sweatshirt, leggings, and white sneakers are a foolproof choice for laid back autumn activities like apple picking or going for a hike.
I’d bring a denim or leather jacket just in case it gets chilly.
12. Jumpsuit with Cape and Jeweled Mules
If you want to make a dramatic entrance, a caped jumpsuit definitely demands attention.
To ground this bold look, finish your ensemble with some understated mules. It’s such a power move.
13. Printed Pants, Loafers, and a Cropped Sweater
Let your printed pants be the star of your date night outfit. To do this, just pair them with simple loafer flats and a cropped sweater.
This look is the definition of understated chic.
14. Sweater Dress and Tall Boots
A knit sweater dress is so cozy but still feels feminine for a fall evening.
If you want some leg coverage, you can layer sheer tights underneath and pair the dress with over the knee boots.
15. Faux Leather Pants, Heels, and a Lacy Cami
Leather pants might seem a little intimidating, but they are surprisingly versatile for a night out.
Create some contrast by combining faux leather pants with a delicate camisole and some heels.
16. Jeans and a Button-Up Shirt
Here’s a foolproof date night look: a classic button up shirt with jeans or trousers. You can tuck the shirt in or just leave it out over your bottoms.
Complete the outfit with a medium weight jacket like a denim, corduroy, or leather one. A pair of heeled booties or ankle boots will polish off the look.
17. Metallic Faux Leather Dress and Stiletto Heels
Shine bright in a metallic faux leather dress! This eye catching silhouette is a perfect match for stiletto heels. Finish the whole look with a sleek top handle bag.
18. Bodycon Dress and Pointed-Toe Pumps
A bodycon dress is made to hug your best assets. For some leg lengthening appeal, add a pair of pointed toe pumps.
You can polish off this bombshell look with a bold red lip and some chandelier earrings.
19. Oversized Pullover and Bike Shorts with Sneakers
Bike shorts were everywhere this summer, giving outfits major athleisure vibes.
You can carry that look into fall by pairing them with an oversized knit pullover or sweater. Add white sneakers and a beanie for a sporty date look.
20. Slip Skirt, Blouse, and Pointed-Toe Heels
A midi slip skirt in a jewel toned hue feels so luxurious. For some effortless sensuality, pair it with a V neckline blouse and pointed toe heels that have ankle straps.
I’d keep the accessories minimal for this one.
21. Sweater and Skirt with Tall Boots
If you’re going for an effortlessly chic vibe, try pairing an oversized sweater with either a knit skirt or a leather skirt.
Finish the outfit with some versatile over the knee or knee high boots. A scarf would be a great accessory to tie everything together.
22. Embellished Midi Dress and Block Heels
An embellished midi dress brings the perfect amount of sparkle to a date night.
I think pairing an ornate frock like this with block heel sandals is a great way to balance the look.
23. Graphic Sweatshirt and Jeans
You can give your favorite graphic tee an upgrade by pairing it with distressed jeans or leggings and a bomber jacket.
Complete this casual look with some crisp white sneakers. This outfit is perfect for outdoor autumn activities.
24. Faux Leather Pencil Skirt, Silk Camisole, and Ankle-Tie Heels
Putting a faux leather pencil skirt with a slinky camisole creates the illusion of a dress.
For some date night elegance, tie the look together with ankle strap sandals and minimal accessories.
25. Off-the-Shoulder Cocktail Dress and Ankle-Strap Heels
An off the shoulder mini dress shows just the right amount of skin.
For a stylish night out, this sultry neckline is a perfect partner for ankle strap heels and a glittering minaudière.
26. Satin Slip Dress, Stiletto Pumps, and a Fur Coat
A satin slip dress just oozes old Hollywood sophistication. You can layer a fur coat on top for some diva esque glamour.
Finish it off with sparkling jewelry and stiletto pumps.
27. Midi Skirt with Slit, Long-Sleeve Crop Top, and Ankle Boots
A midi length skirt with a dramatic slit shows off the perfect amount of leg. Pair it with a long sleeve crop top and ankle boots.
Some simple gold jewelry completes this sophisticated look.
