The best fall date night outfits

Fall date night outfits can be hard to pull together. This blog post provides inspiration for what to wear on a hot (or even mild) date night in fall of 2022.

Oh, the ole first date. Or any date for that matter in my 20s and 30s.

Deciding what to wear. Taking forever to do your hair and makeup. 

Did you stop blow drying your hair every couple of minutes to make sure you didn’t miss your date calling you a la Bridget Jones’s Diary?

Yeah, me too. You did not want to miss that last minute call with a change of plans, pick up time, or (Lord please no) the cancellation.

The goal was to look irresistible. Make your date think— I cannot let this one get away.

But if you’re like me, this not your dating goal anymore. It’s to show up ready to have fun, laugh, and connect with your date. Whether it’s your significant other or a first date.

When I started my research on fall date night outfits my Google report was full of sultry looks. Lots of tight, short dresses and skirts. And cutouts, loads of cutouts. 

I’m not sure about you, but these days my date nights are all about comfort. I want to wear something flowy as I’m eating my overpriced (but yummy) vegetarian cassoulet and drinking my red wine at the local French joint. 

Or cozy if we are going to watch a movie (which we usually do at home). But it still counts as a date in my book. We don’t Netflix and chill like the “kids”. We usually Netflix and fall asleep on the couch. 

No matter what my forever date and I are doing, I want to look cute for our special night or late afternoon (let’s be real here) out. But I do NOT need anything fitted, revealing, or even that has buttons. The outfit ideas Google fed me did not line up with my desires for a fall date night outfit. 

So what do you wear for a fall date night? 

You can look sexy and comfortable at the same time. Part of looking good is putting in the effort. It’s being intentional with your clothing choices. Not picking up the outfit from yesterday that’s thrown over the back of the chair. 

For women over 50, date night should be all about feeling like yourself. Elastic waistbands and loose-fitting dresses are the new sexy. This goes for first dates, last dates, or your millionth date with the same person. 

If you agree, then you should love the looks I’ve pulled together for fall date night outfits 2022. These are pretty, feminine, sassy, and all comfortable. Links to more details about all of the items are below the photos.

There may be affiliate links in this post. This means if you click a link and make a purchase, I may get a small commission at no cost to you. This does not affect what I include in my blogs, only the best for you.

Jeans for date night

Jeans are a date night staple, so I had to include them. These are soft cotton more like denim pants. I paired them with a cashmere tank top and a corduroy double-breasted blazer for warmth and texture. The floral earrings take this look over the top and tie together the shades of pink. I added a dusty rose vegan leather clutch (we used to call this pleather back in the day) and velvet rose gold sandals. These add a bit of sass and sexy to this get-up. 

Pink double breasted corduroy blazer, stone colored cashmere cami, long floral drop earrings in shade of pink, light pink vegan leather clutch with chain strap, rose colored velvet sandals makes a great fall date night outfit
Pink corduroy blazer/ cashmere tank top/ denim pants/ flower drop earrings/ pink vegan purse/ velvet sandals

A sweater and skirt

A classic cashmere polo sweater with a rose gold slip skirt are great basics that you can wear over and over. If you add a fun magenta faux fur with a coordinating sparkle clutch, and kitten heels (can these please be in style forever and ever) it becomes a pretty date night outfit. I would keep the jewelry simple and in the gold family. Not only is this a great date night outfit idea, but it also shows you how to spice up your closet basics. 

Ivory cashmere polo, magenta faux fur coat with gold buttons, rose gold slip skirt, magenta crystal clutch, nude colored kitten heels.
Cashmere polo/ faux fur jacket/ rose gold slip skirt/ shimmer clutch purse/ nude kitten heels

A statement dress (mumu style)

This is something I wore recently on a date night. It’s easy to wear, and in no way confining. You can tie it up at the neck, but for a sassier look, I left it open. I wore this with gold low heeled slides and flower earrings. You could also wear this with a belt, a sandal that has a higher heel, or chunky loafers.

Please notice my furry friend in the corner of the picture. He would not get out of the way. He’s not for sale (at the moment anyway).

black dress with white flowers, and pink outline. Gold sandals and cute dog in the corner of the picture. One of my recent fall date night outfits
Housecoat (similar style)/ gold woven slides

The sweater dress

This paprika-colored knit dress is so cozy and pretty. I put it with a similar colored boot for a monochromatic look. This also elongates your legs so they don’t look chopped off with a change in the color of the boots. Add these gold bauble earrings and a chocolate woven bag and you’re off to dinner. For a sexier look, you could wear black strappy sandals. This dress would also be a great option to wear Thanksgiving dinner.

Gold bauble earrings, paprika colored wrap front sweater dress, chocolate woven bag, tall boots is one idea for fall date night outfits.
Gold bauble earrings/ paprika wrap knit dress/ chocolate woven bag/ tall boots

A casual fall date night idea

Need a cute movie date night outfit? Try a puffy-sleeve top with coordinating wide-leg pants. The elastic waist allows for plenty of popcorn consumption and won’t dig into your stomach as you sit through the movie. I put this with green sneakers from a fun new brand out of LA that I’m loving. 

The shades of green in the purse pull in the colors from the shoes. This is a sweet look that is also comfortable. You don’t have to look like a vixen to feel pretty or sexy. You can wear something that feels good, is comfortable, but shows that you put the effort in. 

Bronze glitter sunnies, black and white puff sleeve sweatshirt, matching wide leg sweatpants, green cross body bag and green and white leather tennis shoes. This is a great option for a casual fall date night outfit.
Glitter sunnies/ puff sleeve sweatshirt/ wide leg sweatpants/ green cross body bag/ green and white tennis shoes

Sexy is a state of mind. As you head out for your date nights this fall, I hope you can find ways to dress like yourself. To be comfortable and confident. Nothing is hotter than confidence. 

You can recreate these outfits with items in your closet. A lot of these items are basics or work wear that I spiced up. Or if you’re in need, pick up a thing or two. I also have some great fall pieces in this blog about my favorite fall pieces. Or, this blog about building out you fall capsule wardrobe. You can find date night ideas all over the place, you just have to accessorize to make them sassier for that one-on-one time with your significant other or someone you’re interested in getting to know. The key is to make the outfits your own.

And by all means, if you feel sexiest when wearing tight short clothes with lots of buttons, then do it. Go forth and enjoy your date night outfits this fall. 

Wishing you much success in love, style, and comfort. 



I show women over 50 how to get noticed, stay relevant, and be connected through their wardrobe. Getting dressed is something you have to do each day, why not make it fun.



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