Fall Dinner Outfits Over 50: What to Wear for a Casual Dinner or Date Night

Getting dressed for a casual fall dinner sounds like it should be easy. Then you start wondering exactly how casual “casual” is. Are we talking jeans? A dress? Do I need a blazer? If you’ve ever wondered what fall dinner outfits over 50 should actually look like, you’re certainly not alone. And if Joe is waiting on me, how many outfit changes do I get before he starts asking if we’re ever actually leaving? Lol!

I think the hardest part about dressing for dinner these days is that almost anything goes. You can walk into the same restaurant and see someone in jeans and sneakers sitting beside someone in a dress and heels. My goal is usually to look a little more polished than I did running errands that afternoon, but still be comfortable enough to sit through dinner and enjoy myself.

That balance between comfort and looking put-together is something I talked about recently in 4 Clothing Brands I Rely On for Comfortable, Polished Style Over 50. I’m at the point where I’m not interested in choosing between the two, and thankfully, I don’t think we have to.

Fall makes casual dinner dressing especially easy because we have so many good options. A dress and a nice bag can be enough on their own, while jeans, a pretty blouse, and a blazer can take something very casual and make it dinner-ready. Most of the time, you don’t need an entirely different wardrobe. You just need the right combination.

This post has been updated with current recommendations and links for a better reader experience.

How Dressy Should You Get for a Casual Fall Dinner?

My rule is simple: think about where you’re going, then go one small step dressier than your everyday running-around clothes. For a neighborhood restaurant, nice jeans and a blouse might be plenty. If you’re headed somewhere a little nicer, switch the jeans for trousers or wear a dress.

Comfort still matters. If I’m tugging at my waistband before the bread basket arrives or wishing I had worn different shoes before we’ve even ordered, I chose poorly. At this stage of life, I want to look put-together, but I also want to enjoy my dinner.

Here are some easy outfit formulas I use or would reach for when I want that middle ground between everyday casual and dressed up.

A Simple Dress and Leather Accessories

A simple dress is probably the easiest answer when I don’t feel like putting an entire outfit together. This black Frank & Eileen maxi dress is a good example because the clean silhouette does most of the work for me. The black looks polished enough for dinner, but the style itself is relaxed and easy to wear.

I added the warm leather bag because black can sometimes look a little severe on its own. Cognac or caramel leather softens it and gives the outfit more of a fall feel. Depending on where I was going, I could wear this with loafers, flats, low boots, or even a simple sneaker for a very casual dinner.

A Printed Dress With a Long Cardigan

A printed dress is another easy starting point because you already have color and interest built into the outfit. I wore this red floral midi dress with a long brown cardigan, and I like how the cardigan tones down the dress and makes the whole outfit feel more relaxed.

This is also a good formula when fall weather can’t make up its mind. You have the cardigan when the temperature drops or the restaurant decides it needs to be approximately 42 degrees inside, but you can take it off if you get warm. Lol!

You could do the same thing with almost any printed dress you already own. Pull one of the quieter colors from the print for your cardigan, jacket, shoes, or bag, and the outfit immediately feels more pulled together.

A Skirt, Sweater, and Suede Jacket

This outfit is a step dressier, but it still doesn’t feel like I’m headed to a formal event. The mix of the plaid skirt, sweater, and suede jacket gives it plenty of fall texture, and everything stays in a soft neutral color palette.

This is the kind of outfit I’d choose for a nicer restaurant, dinner somewhere special while traveling, or an evening when I simply felt like dressing up a little more. The pointed-toe booties make a difference here, too. You don’t need a tall heel to make an outfit look dressier.

Wide-Leg Jeans, a Pretty Blouse, and a Blazer

This is probably the formula most women will get the most mileage from:
jeans + feminine blouse + blazer + loafers.

I recently tried these Talbots Classic Jean Trousers in Richmond Wash. The wider trouser-style leg gives them a more polished appearance than a very casual jean, but they still feel like denim. That makes them a nice middle ground when dress pants seem like too much for where you’re going.

The Ann Taylor Seashell Eyelet V-Neck Popover adds the feminine detail I like with a more structured jacket. The eyelet keeps the outfit from drifting into office-wear territory, which is important when we’re trying to dress for dinner instead of a board meeting.

For a fall layer, the Talbots Herringbone Fitted Blazer brings in texture without requiring a lot of other accessories. Finish it with the Quince Italian Leather Penny Loafers, and you have an outfit that feels polished but still very wearable.

This is also a formula you can recreate from your own closet. Your jeans don’t have to be wide-leg, and your blouse doesn’t have to be eyelet. The idea is simply to combine one casual piece, one feminine piece, and one structured layer.

Dressier Pants With Soft Neutrals

If jeans aren’t your thing, or the restaurant calls for something a little dressier, trousers are an easy swap. These Tommy Bahama Sunset Key High-Rise Cropped Pants are a pair I tried recently in a size 8. I liked the cropped wide-leg shape on me, and that warm camel shade works beautifully with ivory, black, navy, olive, chocolate, and other fall colors.

I especially like the idea of pairing them with the Ann Taylor Seashell Eyelet V-Neck Popover and a light neutral blazer. The Talbots Shetland Blazer adds an extra layer without making the outfit feel dark or heavy.

Add the Quince Italian Leather Penny Loafers, a leather bag, and some simple gold jewelry, and you’re done. This would work for dinner with Joe just as easily as dinner with girlfriends or another couple.

A Sweater Dress When You Want One Piece and Done

Sweater dresses earn their place in a fall wardrobe because there isn’t much styling involved. You put on one piece, add shoes and jewelry, and you’re dressed. The trick is finding a shape you actually feel comfortable wearing.

The Quince Mongolian Cashmere V-Neck Midi Dress has the simple V-neck silhouette I tend to gravitate toward. The chocolate brown also makes it easy to pair with cognac, camel, cream, or gold accessories, and you could wear it with a loafer or low boot instead of a heel.

If you prefer more movement through the lower half of a dress, the Jessica Howard Long Sleeve V-Neck A-Line Sweater Dress gives you a different shape. The A-line skirt moves away from the body instead of following every curve, which some women prefer in a knit dress.

I haven’t personally worn these two dresses, so I’m looking at them as shopping options for recreating this outfit formula rather than telling you how they fit on me. I’d check the garment measurements and reviews before ordering, especially with sweater dresses where fabric and fit can make a big difference.

Comfortable Shoes Can Still Look Polished

There was a time when “going out shoes” almost automatically meant heels. I’m happy we have moved past that little rule. Lol! A loafer, pointed-toe flat, low bootie, or small block heel can look every bit as appropriate for dinner.

The Quince Italian Leather Penny Loafers are an easy example because that warm brown works with denim, camel, chocolate, navy, cream, and many of the colors we wear in fall. A loafer also gives jeans or trousers a more finished appearance than an athletic sneaker while still letting you walk from the parking lot without regretting your life choices.

Easy Fall Dinner Outfits Over 50 Don’t Have to Be Complicated

If you’re ever unsure what to wear, I’d start with what you feel comfortable in and then make one part of the outfit a little nicer. If you want jeans, add a pretty blouse or blazer. If you want a simple dress, add a great bag or shoes. If you’d rather wear pants, choose a richer fall color and pair them with a polished top.

You don’t have to wear heels, squeeze into anything uncomfortable, or buy a completely new outfit every time somebody asks you to dinner. At this age, I already know I want to look stylish AND enjoy my meal. If Joe gets a nicely dressed date who isn’t complaining about her shoes before dessert, I’d say everybody wins. Lol!

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