24 Dress to Impress: From Casual to Chic

Impress your friends/date/mom/literally anyone. Dress to Impress: From Casual to Chic

We enjoy dressing for the office as much as the next person, but the “casual event outfit,” where you get to impress everyone with your exceptional style (usually while eating food or having drinks), is a fun level up. A casual dinner can be with friends, the person you’re seeing (or would like to date), family, work buds, or casual acquaintances—and it’s one of the easiest places to inject some style into your outfit. The vibe can be “I’ve just come from work” all the way to “I went home, changed, and now you’re getting a whole new outfit,” but all along the spectrum there are opportunities to look and feel cool.

A cool dinner outfit is about thoughtful layering, depending on the circumstances. In colder weather, a coat gets you there but then is taken off; a vest, sweater, or even a sweater vest can be added or taken off depending on the temperature of the restaurant, and the whole look has to work no matter which layer you have on. Probably the most important part: You have to be comfortable enough to eat and move around. I maintain that a casual dinner outfit should be functional so that you can actually eat.

If you’re so bored with your latest dinner outfits and need some fresh takes, or you’ve got an important event coming up (a date you’re excited about, perhaps!), keep scrolling for the casual dinner outfits you can emulate immediately.

Double Denim

Starting with the classic Canadian tuxedo, a double denim look (with two pieces that are close in color but not exact) is such a fun, surprising fashion choice. A tweed blazer is the perfect outerwear.

A Crop Jacket

There’s just a hint of “polished professional” here, but when combined with the jeans and cool shoe, it’s a toned-down kind of vibe. The surprise here is the crop top, but if that feels like too much, opt for a white tee or tank.

Thoughtful Layering

This look contains multitudes: The structured shirt and chinos feel workplace adjacent, but the mules and cap skew more casual. The plaid bag and sweater over the shoulders tie everything together (pun not intended).

A Great Coat

If you want to look stylish but aren’t interested in spending hours in front of your closet, pick easy base layers (white turtleneck and jeans), then go with a cool coat and contrasting bag to feel instantly elevated.

A Statement Collar

Alternatively, if you don’t want to go big on the coat (or it’s warmer weather), pick one aspect of the outfit and maximalize it. I love that this collar is absolutely huge, but the rest of the look is basic—and works for transitional weather.

A Puffer Coat

Puffers don’t have to be boring! This one is in the style of a shearling bomber jacket, but looks like it was inflated like a balloon. The extra width makes a fun statement…plus you’ll be super warm.

A Big Vest

If a coat feels so basic, an oversized vest is your pick. It’s an underrated layering piece: It provides some warmth when you’re outside, but it’s breathable enough so you might not have to take it off when you’re inside. But it’s easy to take off and stow away if you need to!

A Contrasting Bag

If you’re starting with a simple base layer like a dress but don’t want to add a ton to it (or if the weather is warmer and you can’t layer) go for a statement bag and shoes instead. One way to uplevel is to match your lipstick to your purse!

A Casual Button-Down

In warmer months, you can still layer by using an Oxford shirt worn open as a jacket. Wearing a tee you like underneath allows you to take the outer layer off when you need to—you could even tie it around your waist—but maintain some structure in the outfit when it’s on.

Cool Boots

With the caveat that you need to be able to walk in whatever footwear you choose, a casual dinner can be a nice way to break out your statement shoes. This is particularly true if you don’t have to walk a mile to get to the restaurant, but you do you regardless of the context.

A Tonal Look

A casual dinner look that might have started out as a casual workwear look, this outfit goes from the office to the restaurant with ease. The relaxed element comes via the jeans, and the professional chic elements come from the matching long coat and satchel.

A Mini

If you want to feel cute and stay as warm as possible (a cold weather date, perhaps?!), pair your miniskirt with tights, a matching cardigan, a big coat, and stiletto boots. Once you take your layers off, it gives a very different vibe.

A Crop Top

Weather and restaurant permitting, the crop top can absolutely be dressed up. Just make everything else in the look a tiny bit more dessy, from the coat to the non-distressed jeans to the leather fashion sneakers. The earmuffs give an unexpected fashion flair.

Interesting Headgear

Who knew that a studded French beret is the finishing touch your outfit needs? This is clearly a cold weather look—and the lace-up boots are functional as well as fashionable—but your accessories can add an edge to your outfit even when you’re dressing to be warm. (And you can leave the hat on when inside!

A Maxi

In warmer weather, your casual dinner look should still be fun but functional. This pretty maxi skirt still allows for freedom of movement as you share apps with friends. If you spill your food all over yourself as I do, though, maybe opt for a color other than white.

Fashion Slippers

Just because you’re outside doesn’t mean you can’t be cozy! If you’re swapping out your work heels for something flatter and more comfortable, just make sure they’re not old and tattered. The socks help make the shoes feel more thoughtful instead of haphazard, too.

Statement Jewelry

The best, easiest way to dress up a simple outfit? Accessories! The big chunky necklace is obviously the star, but don’t sleep on the studded quilted bag to add some dimension too. Rings and a matching mani take it over the top.

Sparkle

Speaking of jewelry! This base layer here is very simple white-on-white (make sure you layer with a tank underneath if the restaurant might be warm). Then the gorge butterfly bag, chunky rings, and layered chokers instantly add a cool-girl factor. Opt for sliiiightly shorter heels if you’re going to walk a lot.

Black Leather

When in doubt, layer a leather or vegan leather jacket over your outfit. It’s rarely a bad choice, and it usually adds a “tough” vibe that might be missing. This is a smart layering outfit, so the jacket and sweater can come off if the temperature inside is warmer.

All-White

If a black suit feels too boring, just switch it to another color. This cream suit set doesn’t feel as heavy as a black suit; The rolled up hems also feel a bit casual, but the suit itself is structured enough to not look sloppy. (Wear a tube top underneath for layering purposes.)

A Surprising Color

I kind of want to be invited to a nice dinner so I can literally replicate this exact outfit. Silver/gray are cool colors at the moment (but they’re also just cool colors in general, trendiness aside) so going tonal with a pearl-studded cardi and silver-coated denim is an unconventional and amazing choice.

Some ’90s Inspo

Opting for a handbag, scrunchie, and split hem jeans will take you right to 1997. So to avoid looking costume-y, bring in some classic pieces like a brown bomber, button-down shirt, and pointed-toe heels. It’s a really nice balance.

A Thematic Bag

I will admit that I first thought of this look for a dinner date, and I stand by it. Is it a little corny to wear your intentions on your shoulder? Sure, but how cute is that bag?! The right person will understand immediately and think it’s funny.

Dress to Impress: From Casual to Chic