Every week, David and I pencil in a date night. It doesn’t always happen (sometimes we find ourselves with takeout and our of-the-moment Netflix show), but when it does, I’m usually racking my brain for fall date night outfits. Maybe it’s for lack of time (fall schedules are busier) or predictability (mild one day and freezing the next). Whatever the cause, in fall, I’m more likely to be found staring cross-eyed at my closet one hour before a reservation thinking, “What in the world do I wear?”
If you’ve ever done the same, you know how indecision can dampen an entire evening. After all, date night should be fun, not frustrating. To help you (and me!) arrive at an outfit quicker, I came up with five back-pocket fall date night outfit ideas for those busy weeks. Whether you want to look cute, classy, or sexy, will be indoors or outdoors, and whether it’s warm, mild, or properly cold, there’s a fall date night look to fit the bill below!
Note: Click any collage to shop the date night look.
Fall Date Night Outfit Inspiration
1. Dark Jeans, Silk Top, Moto Jacket, & Shoe of Choice
This is a classic going out combo and my personal go to for hitting the town in autumn. Dark denim has a dressy feel, and I recommend ankle-length skinny jeans as they go with nearly any shoe, from flats to heels and boots in most shaft heights. I usually opt for strappy heels to show some skin, but if it’s cold, try pumps or stiletto boots. On top, a blouse, bodysuit, or camisole in silk, satin, or a similar drapey material will elevate the denim even further. There are thousands of tops out there to suit your preferences, from sexy lace-embellished camis to long-sleeve bodysuits and halter tops in moody fall tones. If it’s chilly out, a chic suede or leather jacket will complete the look!
2. Fall Dress, Outerwear of Choice, & Shoe of Choice
There’s nothing more romantic than dresses. And bonus: they’re incredibly easy to style. I love floral dresses for fall as they pair equally as well with knee high boots for a nice dinner date as they do with loafers for casual dates (think outdoor brewery) and sneakers for active dates (apple picking). If you layer a jacket for warmth, pay attention to its length. Cropped jackets look best with long dresses as they accentuate the waistline, but you can pull off a longer coat, coatigan, or cardigan as long as it’s roughy 3/4 the length of the dress or reaches past its hemline.
3. Knit Dress & Comfortable Shoes
There are so many opinions about what to wear on a first date, but my number one piece of advice is to wear something that feels truly you. Feeling natural in your clothes will translate into easier conversation, less tension, and a more enjoyable experience. If you’re stumped on what best represents your personality, here’s a no-fail fall date night outfit that flatters every body type: a knit dress (like this, this, or this) and block heel pumps or booties. A sweater dress is a one-and-done piece, giving you more mental space to think about more important things (like what you’re going to talk about!) and block heels fare well in most date situations if you don’t know where you’re headed. Finish the look with a moto jacket, duster cardigan, or layering coat if it’s chilly out.
4. Sweater, Dark Bottoms, Pumps, & Outerwear of Choice
Black jeans and faux leather leggings are a great way to rise to the occasion if you’re headed somewhere dressier or want to make a statement without being too over the top. If you go the leggings route, I recommend Commando because they have a slight sheen. L’AGENCE makes excellent coated jeans if faux leather leggings are too trendy for you. My favorite jeans in black are by Everlane and Paige. On top, wear a v-neck sweater (the décolletage area is so feminine), and any outerwear. Everything from a neutral shacket to a luxury blazer or drapey camel coat is game. Finish the look with classic heels. I love Sarah Flint pumps for dates as they have a wider toe bed and added padding to keep you comfortable!
5. Slip Skirt, Fitted Top or Sweater, Boots or Heels, & Blazer
In neutrals or a monochrome palette, this look screams sophisticated and elegant. A maxi slip skirt is ideal for dressy occasions, but a midi skirt can work as well. I like to wear an open-toed shoe for a little skin, but if it’s freezing, a pointed-toe bootie can work as well. There are two routes you could take for the top: a fitted bodysuit, which will counter the flowy nature of the skirt, or lean fully into fall textures by contrasting the satin skirt with a chic sweater. The sweater shouldn’t be too long or oversized. With either, layer a double breasted blazer.