I was thinking recently about how much things have changed now that the kids are grown and we’re in this new season of life. Even though they’re all still living at home in some capacity, Paul and I aren’t running from band practices to ball games or planning our weekends around school schedules anymore. Our social lives have simplified, too. These days, “going out” really just means going out to dinner.
While that may sound ordinary, it’s often the one time all week it actually feels fun to get dressed. The thing is, most places we go are pretty casual. Even at nicer restaurants, I rarely see anyone dressed up—and I don’t ever want to feel like the dressiest person in the room. The trick is figuring out what to wear to dinner so you look elevated, but not overdressed.
J.Crew Chiara Topcoat (6) – splurge (spend option / save option) // Jenni Kayne Flynn in Oatmeal (S) (similar for less) // AGOLDE Harper (29) (similar for less) // Vince Hillside suede ankle boots (similar here and here) // similar belt // Mulberry bag (option) // Tom Ford sunnies (option) // Jenny Bird Florence Hoops // Jane Win HOPE Pendant
For me, elevated doesn’t mean uncomfortable or over-the-top. It simply means looking pulled together and intentional, even when the outfit starts with jeans. And let’s face it… my outfits almost always start with jeans.
What to Wear to Dinner (Without Feeling Overdressed)
I have a feeling many of you are in the same boat, so I thought I’d break down how I put together “going-out” outfits that feel special without feeling overdressed.
Start With the Right Foundation
Jeans are usually the most practical starting point, but not every pair works for this kind of outfit.
What jeans work best for going out looks:
- Clean hems with minimal distressing
- Straight-leg, wide-leg, or subtle flare silhouettes that pair well with a dressier shoe
- Denim that holds its shape and doesn’t feel sloppy
- Medium to dark washes, as well as black or white denim
- Light washes can work, as long as the cut feels modern and it makes sense for the outfit
These details help jeans feel more like date night and less like something you just threw on to run errands.
In this case, I went with light-wash jeans because I wanted to build an outfit using all light neutrals. I chose a more structured pair in a full-length, relaxed straight-leg silhouette that feels current right now. They’re also long enough to require a heel, which helps dress up the lighter wash and keeps the look from feeling too casual.
Upgrade the Top
When you’re wearing jeans on the bottom, it helps to be a little more thoughtful up top—something beyond an everyday tee or sweatshirt.
Tops that tend to work well for dinner or date night:
Even very minimal tops can feel elevated when the fit is right and the fabric either feels luxe or has a bit of structure. It’s often the easiest way to take a jeans outfit from daytime casual to dinner-ready without overthinking it.
For this look, I wore a fine-gauge cashmere V-neck in a soothing oatmeal shade, which always feels a bit dressier to me than a crewneck. It’s a simple piece, but the quality of the fabric creates a luxe contrast against the more casual vibe of the light-wash denim.
Shoes Set the Tone
When you’re wearing jeans to dinner, the shoes are usually what make or break the outfit. The right pair can turn an everyday look into something dinner-ready in seconds.
Shoe styles that tend to elevate denim:
- Pumps or slingbacks
- Pointed toe flats or Mary Janes
- Sleek ankle boots with a narrow toe and/or a bit of a heel
These styles strike a nice balance between looking put together and still feeling wearable.
When I’m worried an outfit might veer into overdressed territory, I often reach for a pointed-toe flat or a Mary Jane. The lack of a heel keeps things from feeling too fussy, while the refined shape still feels appropriate for dinner.
In this case, the sweater is a simple style and the denim is a more casual wash, so I opted for suede ankle boots with an almond toe and a 3.5″ heel. That little bit of height helps the outfit read more like a date-night look without feeling overdone.
Add a Polished Layer
A good third piece can instantly make your date night outfit feel finished. When you’re wearing jeans, it’s often the difference between looking like you’re headed out for errands and looking ready for dinner.
Instead of defaulting to a cardigan, which can read more workwear than dinner out, try something with a bit more structure, like:
In this case, I’m dressing for winter in the Northeast, so my top layer is my coat—a long, relaxed style in a luxe wool-blend fabric with a touch of cashmere. The camel color works beautifully with the oatmeal sweater and light-wash denim, and it also ties in with the boots for a cohesive finish.
Finish With Thoughtful Details
When the outfit itself is fairly simple, as mine tend to be, adding one standout detail or a few subtle points of interest can go a long way toward making it feel finished. That might be a great belt, a piece of jewelry, a statement bag, or even a standout shoe.
The goal is balance: choose one focal point or two complementary pieces, and keep the rest of the look clean so nothing feels busy. This matters even more if you’ll be taking off your coat—you still want to feel like you’re wearing an actual outfit.
In this case, I added a few elements that work together rather than relying on one main statement piece. A bold gold pendant necklace draws the eye up toward my face, with gold double-hoop earrings that complement it nicely—they’re noticeable without competing.
The belt is in the same color family as the shoes and coat, but slightly darker, which helps anchor the look and define my waist. I tied it all together with a cognac leather handbag and finished the look with brown tortoiseshell sunglasses.
A Few More Elevated Outfits to Wear to Dinner
I focused on breaking down one outfit in detail because I think that’s often the most helpful way to see how all the pieces work together. But to show how this approach can translate to different looks, here are a few other dinner outfits I’ve worn that follow the same basic formula.
Washed Black Jeans + Short Cardigan + Black Boots + Gold Jewelry
MOTHER Hustler Roller Sneak (30) (similar for less) // similar Vince cardigan (budget option) // Madewell cardigan (M) // similar boots // Jane Win HOPE Pendant
Even though the featured look includes light-wash jeans, black denim is my go-to starting point for most dinner-out outfits, and these MOTHER Roller wide-leg jeans in washed black are a favorite. I especially love them paired with a shorter cardigan worn buttoned up like a pullover—it feels simple, but still put together.
In both of these outfits, I added black boots to keep the bottom half cohesive, then finished things off with gold jewelry and a long black wool coat (not pictured).
Black Jeans & Sweater + Black Boots & Belt + Faux Fur Leopard Jacket & Animal Print Bag
leopard jacket (S) // Jenni Kayne Flynn (S) (option) // FRAME The Lax (29) // Sam Edelman Saige Bootie (8.5) (option) // FRAME belt (M) // Clare V. Petit Moyen // Jenny Bird hoops // Jane Win HOPE Pendant // Lili Claspe Adva Cuff
I wore this look to dinner with friends at Christmastime, and this is about as dressy as I get these days! I started with a simple black base of washed black jeans and a black sweater.
Style note: Washed black denim feels more modern to me than inky black jeans, and in this case, I especially like how it creates a subtle contrast against the sweater and boots.
I added sleek black leather heeled ankle boots and a faux fur jacket that is both the top layer and the statement piece. A black leather belt with gold hardware and gold jewelry add interest and help tie everything together. True confessions: I originally planned to carry the animal print bag, but paired with the faux fur jacket it felt like a bit much, so I swapped it for a plain black bag before leaving the house.
Light Wash Jeans + Plaid Coat + Brown Sweater & Boots + Animal Print Bag
EVEREVE Wesley Plaid Coat (S) // Nordstrom Cashmere Crewneck (M) // AGOLDE Harper Straight (29) // Sam Edelman Saige Bootie (8.5) // Clare V Petite Moyen Messenger // Tom Ford sunnies
This look started with the brown-and-blue plaid coat. I used the same light-wash jeans as the featured outfit, then added a brown sweater and brown suede boots to bookend the look. The leopard bag brings in a bit of pattern mixing, and I finished it off with a brown belt with gold hardware, the gold pendant necklace, and brown sunglasses.
Medium-Wash Blue Jeans + Brown Top + Leopard Mary Jane Flats + Beige Trench & Statement Jewelry
London Fog trench (S) // Harper Matte Coated Tee (S) // MOTHER Insider Flood (30) // Dolce Vita Roslyn (8.5) // similar woven crossbody // beaded necklace // link necklace // FRAME belt (M) // Tom Ford sunnies
Finally, an example with flat shoes. The mesh leopard Mary Jane flats are what take this outfit from errands to dinner or date night, although I’d totally wear this to run errands, too.
The chocolate-brown coated tee with its flattering V-neck and center seam, feels a bit more elevated than a typical cotton T-shirt. The beige trench adds structure, and the contrasting buttons and plaid lining pick up the brown tones from the top and shoes.
I finished the look with a textured camera bag in chocolate brown, a bold brown beaded necklace layered with a gold link necklace to dress up the neckline, and a belt and sunglasses.
Style note: It’s easy to overlook those final details, but they’re what really pull the look together.
The Takeaway
If you’re ever unsure what to wear to dinner, this is the framework I come back to—modern denim, an elevated top, a great pair of shoes, a finishing layer, and a few thoughtful details.
Your turn! What outfit formulas do you rely on to make your going-out looks feel special?
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44 Responses
I like the look of the main outfit you shared! Very cohesive and well thought out. Ecru denim would also look pretty or even a flowy cream pant in place of the denim. (Looking at you Aritzia Thesis or Lodge)
One thing that caught my attention is not wanting to be the most dressy outfit at the restaurant. That made me pause and think if I would mind being the most dressed? I don’t think so. I think many of the places we go, some might interpret as their “nice” choice and possibly go before theatre (which also leans casual anymore🤷♀️) so they may show up in a more formal outfit when the restaurant might be more “everyday” for me so I show up in an outfit similar to your examples. I don’t know… it simply made me pause to think about my own approach and I think I’d be okay being the most dressed. Phew! I hope this overthinking so early today is not where my head plans to spend the day!
Lovely post, excellent advice as always!
I don’t think you’re alone in that. I feel like, when asked, most women would say they’d rather be overdressed than underdressed. That’s where I’ve always felt a bit like the odd man (woman?) out… lol. I generally feel the opposite. Unless it is a wedding or a business event or something. But for my day to day, I tend to prefer to focus on the fit and quality and have fun with color combinations, while keeping the general formality more understated. I think knowing that about yourself (whichever side you fall on) is really important as far as finding outfits that make you feel happy and confident. Maybe that’s a post topic in and of itself!
To each their own, although I tend to agree with Shelly. I don’t mind being slightly overdressed. But am I the only one that sometimes gets tired of everything being more casual? I like dressing casual on a daily basis, but for special occasions it seems that there’s so few places to dress up anymore! For something like an anniversary dinner or even fancy Christmas date night, I miss being able to put on a nicer dress and heels without feeling awkward since everybody else at the (supposedly) fine dining restaurant has on jeans and sweats! 🤦🏻♀️
To clarify, I’m talking about “special” occasion dinners. I absolutely wear outfits like the ones you show here for a random Tuesday night dinner! But even on a random weeknight, I prefer to wear nicer jeans with a nice sweater or blouse as opposed to a tshirt with casual jeans or sweatpants!
Yes, I totally feel that way. I WANT a reason to dress up beyond jeans… I am always surprised when we go to nicer restaurants, how casual everyone still looks.
I definitely get tired of most things being so causal and also miss the opportunity to dress up more! There are times where I will dress up when going somewhere nicer than normal just because I think it’s important.
I 100% agree with other you , then again I tend to over dress . LOL . I just can’t get on board with leggings outside of the gym or walking the dog . To me they aren’t really pants .
I just went through this Friday night! I had dinner out with friends and really didn’t know what to wear… I didn’t want to feel overdressed and of course our weather was bitter cold with flurries!
I decided after a few wardrobe changes 😂 to wear straight leg jeans, long sleeve brown tee shirt( it’s a luxe very soft shirt) and my mini ankle Uggs ( for warmth) and topped it off with an oversized brown dress coat from Zara!
I probably should have worn my pointed toe dolce Vita boots with slight heel but my feet just weren’t feeling it that night!
The weather really influences me. I still want to look put together but warm and cozy!
I wish I had worn my faux leather pants with casual sweater ( tee underneath for contrast at neckline) pointed toe boots and dress coat.. but with the weather I just wasn’t feeling it! And it might have been too much… I often like my lifestyle sneakers with my faux leather as it keeps them a bit more casual.
Thanks for these ideas! I’ll definitely be referring to them !
Question? Would leggings and riding boots with a nice sweater topped with oversized coat have worked where it was such a bitter cold evening out? I haven’t worn anything like that out just wondering?
The weather totally affects me too. We had tickets to a play last weekend, and it was soooo cold. I just wore my straight black jeans, an old black sweater, and black ankle boots and put on my black wool coat and plaid scarf. It was an outfit I would normally throw on to go to the mall, but I knew no one would be looking at me and I just wanted to be comfy and warm. Leggings and riding boots isn’t a very current look, and I feel like leggings are cold (unless they’re fleece lined, I guess.) I would be more likely to just wear jeans and ankle boots.
Thank you! Yes I feel like the leggings are best kept for exercise and a more casual look with sneakers:)
I find this very helpful. It’s true dressing up is much less formal now.
My question is taking this guide line to the next level. No jeans but still smart casual.
I really like reading your whole thought process in wardrobe building. It’s been warm and lovely – not gonna lie 😉 – here over the past week that my outfits have looked different, but your advice about using fabrics and textures to signal winter, even if it’s a short sleeve sweater, has been stuck in my mind and so helpful. Mary Janes and pointed toe flats are usually my shoe of choice to wear lately.
I would love to see you style the Gola light blue sneakers that are on the Evereve site right now. I’ve had them in my cart – I think they’re incredibly cute – but hesitating because I’m not sure how much wear I’d get out of them. I thought I saw them on one of your lists of things you’re eyeing.
I think those sneakers would look amazing with white denim. And they would be great with your coloring too!
Very timely article for many of us. One other consideration I find myself going through is what other women in our dining party will wear. We often go out in a group and I wear the look you showed while others in my group are wearing leggings or sweatshirts. I never feel overdressed though, I feel like they probably feel underdressed. Sometimes I feel like part of a Motley Crew when we’re out. LOL. P.S. No one should wear atheleisure out to dinner, unless they are having dinner in an airport.
Interesting, my friends never go out in leggings or sweatshirts. And we live in a very causal area, but if we go out to dinner, everyone is at least in jeans and a sweater.
My sentiments exactly !
My husband & I are SO in the same stage of life as you & your husband with both of our kids out of college and now in their careers… yes, having dinner out is the way we go too and I really appreciate your ideas of what to now wear in this life stage!
I truly enjoy your inspiration!! Please know how much your efforts are appreciated!
Happy (cold) Monday here in Ohio too!
Thank you, Lisa!
Love the looks. Where I live this is about as dressy as it gets for me too. Someday you will be totally empty nested and it feels very strange at first. You are easing into it for sure. Hope Becca feels more at home at her new college.
She is loving it!
Thank you so much for this post. You break it down and make it easy to put an outfit together when you have someone like me that struggles to do so. Do you happen to have the links for the fifth outfit idea with the coated chocolate brown shirt with the leopard flats?
Ooops, sorry about that! I will link it now. Sadly, some pieces are sold out.
I love all of your outfits! You always look so put together. I’m a jeans girl also. I finally purchased my first pair of wide leg jeans. They are so comfortable. I started adding that third piece and that made my outfits look so much nicer. I’m really casual mostly but my husband and I always go out on weekends. Going out to dinner is our going out. Thank you for the post! Have a great day! 😀
I love the belt you’re wearing in the main look, but the link isn’t working for me! Can you share what it is? Thanks!
Sure, mine is a Ferragamo, total splurge! And no longer available, so I was trying to link this Madewell that is a similar size and color.
I’m pretty adept at putting an outfit together that is “leveled up” but not dressy. I’m certain that I am frequently one of the best dressed women when I am out at a casual event or dinner, but I’m fine with it. Sometimes it’s not me that’s “dressy” but everyone else is, well, not elevated at all, shall we say, wearing sweats, athleisure, leggings. I’ve also noticed that friends and family who used to dress pretty well do not seem to do so much now, maybe because it’s a bother or they don’t know what the current fashion is. I was raised not to dress fancy but to look appropriate for the occasion so that’s what I hope I’m doing. Where I DO need help is with outfits that are dressy, like a fancy dinner or graduation, or some other event. That’s when I get stumped, especially in the winter because I don’t want to reveal any skin and I’m very pale. I feel sometimes like a sweater and nice pants are boring but I don’t know what else to wear and stay warm.
I struggle with those too, truth be told! I usually end up in a sweater dress because I don’t really like non-denim pants.
I say Amen to all you said here. Me too.
I don’t know where else to report this. I have stopped getting your daily emails. Are you still doing them?
I sure am! I moved them over to Substack. It looks like your email address is “pending” so maybe you just found the link and signed up? LMK if you need help.
I’ve been following your blog and getting the email updates for 2-3 years now. I *think* I signed up for your substack when you moved over to it. The emails stopped 1-2 weeks ago.
Jo-Lynn I had a dream this past weekend that I met you. You were staying in the hometown where I grew up. You came to my brother’s house since he still lives there. It turned weird when your dogs showed up and were jumping on me. I was trying to tell someone get them off me without being rude. Then I woke up. It seemed so real. Lol.
That is hilarious!
I know. I ate dinner early too and no spicy food. I guess reading your blog caused your pictures posted on my brain. 😊
Good subject for a post. I think the main key is footwear and jewelry — they can elevate the casual look–while still not being over done.
I like your v-neck sweater on the first picture–but too $$$ for me. I also like the leopard fake fur–I like that its darker and more subtle then other spotted leopard jackets out there. Two things I’d like to find or see you find-heh heh–are cute crocodile embossed leather loafers (black or brown) or suede loafers and double hoop looking but one pierce earrings–like you show here–but in silver. Have you ever sported loafers–did I miss that?
Yes, that Jenni Kayne sweater is $$$ – although it does go on sale at times. As an alternative, the Quince one I linked as similar up top is very nice. I would just recommend sizing up for a more relaxed fit.
I don’t wear loafers as much these days, although I’m not opposed. I especially like a loafer mule. The Florence earrings are available in silver, by the way!
OK, I checked out the florence earrings–unfortunately there were too many comments about them being heavy. I need light weight everyday ones. But–hey–thanks for the reply!
Great ideas for date night outfits! I agree that most people do not dress up anymore. We went out to an expensive restaurant for our anniversary and so I dressed up in nice pants and a nice cashmere sweater. As I glanced around there were several people more casually dressed.
We have a casual lifestyle but I do enjoy dressing up for dinner out.
Thank you!
Very helpful post as always! One question about the accessories… I have seen you wear the Jane Win Hope necklace in several posts, but haven’t heard your thoughts on it. I think her jewelry is lovely, but it is on the higher end for plated gold, so I’d love your thoughts before possibly purchasing one… does it feel or look bulky? How does the gold color look mixed with other gold jewelry? What chain did you get with yours? How do you feel about the quality? Any other thoughts would be appreciated! Thank you
I’m of the “rather be overdressed” persuasion. If an outing is meant to be more special, at a minimum, dark wash trouser jeans and a dressy top/shoes. But usually, I would wear a non-jeans outfit with smart accessories.
My mother always taught me it is better to be overdressed than underdressed if you are unsure of your venue
That said I like to dress like “me”
Do I LOVE these jeans, Yes indeed I do. Am I going to add this blouse i love -Yes indeed I am. And I feel Great.
I have developed my own style around and with current trends….I love being me.
If you enjoy dressing up, you are good company. Most of our US presidents enjoyed dressing up for dinner.
The most dedicated to doing so was President Hoover. Men at big name colleges in those days dressed for dinner. He adopted the habit and wore a tux to dinner the rest of his 91 years. Lou Henry Hoover, his wife of 45 years, also a Stanford graduate, dressed for dinner daily with him. She was the first Stanford woman to earn a geology degree, same degree as the future President.
I graduated from West Point; back then, we dressed up for dinner every day, six days a week, following a tradition that dated back nearly two centuries.
I really appreciate the effort you put into your posts . It takes alot of thought and planning. I enjoy the explanations as to what works and why . Thank you for helping us all look more put together !
I found similar ankle boots from Frankie4 in a smooth cappuccino color. I waited until they went on sale. They were still a splurge. They fit perfectly with zero break-in and felt great even having heels.