The Ultimate Guide to Dressy Casual Outfits

The perfect dressy casual look is somewhere between looking effortlessly put together while feeling completely comfortable in what you’re wearing. From heading to Sunday brunch to an after-work event, mastering the dressy casual dress code is all about a balanced ensemble. Put together a few elevated basics, learn how to stylishly layer, and top it all off with the right accessories. In this guide, we’re going to break down how to put together the best dressy casual outfits. If you’re ready to step up your dressy casual game, let’s dive in and get to styling!

Defining Dressy Casual

The term “dressy casual” may seem like an oxymoron, but, according to the fashion experts at Cosmopolitan, it’s just a way to describe an overall aesthetic that means you’re not dressing all-the-way formal, but that doesn’t mean you should be wearing old jean shorts and a hoodie. Dressy casual is somewhere between just rolling out of bed and attending a black-tie gala. You want to look polished without ever trying too hard. 

Think of nice blouses and form-fitting pants paired with chic jackets, but instead of wearing sky-high heels, swap those stilettos for flats or sneakers. No t-shirts with obvious logos or athleisure wear, here, but you don’t want anything too formal, either. Aim for that effortlessly put-together look that’s perfect for casual Fridays and dinner dates. We’re talking dressing up while keeping it comfy and fun.

Key Elements of a Dressy Casual Wardrobe

Versatility and effortless style come together in a dressy casual wardrobe. Dresses are a solid go-to when you add statement accessories or a chic jacket to complete your look. Tops and blouses are easy to dress up or down depending on the occasion. As for bottoms, you’ll want form-fitting jeans and sleek skirts. Outerwear essentials like structured blazers and trendy coats help pull the whole outfit together. Don’t forget about cute shoes and accessories to add personality and a finishing touch.

1. Beautiful Dresses

Beautiful dresses are a great choice for dressy casual looks; just layer up with statement accessories or a chic jacket! Start with a floral, midi, or wrap dress and layer on a denim jacket or blazer. Sneakers can keep it cool and comfy, while ankle booties or strappy heels play up the “dressy” in dressy casual. A statement necklace or drop earrings instantly elevate your dress, so mix and match with different pieces until you find your perfect look.

2. Tops and Blouses

Take your outfit to the next level with our ladies tops and blouses that balance a polished yet playful look. A button-down shirt can be tucked into pants yet worn with rolled-up sleeves for a more laid-back touch. For a more feminine approach, try a flowy blouse paired with a skirt or skinny jeans. On a colder day, knit sweaters go great with high-waisted trousers, while a spring or summer day may call for a silky top underneath a blazer. Add on statement jewelry to your heart’s content for dressy casual perfection.

3. Bottoms That Work

Bottoms can be tricky to navigate when figuring out a dressy casual look, but it’s all about versatility. Try dark-wash jeans dressed up with heels and a blazer or keep it on the more casual side with sneakers and a nice top. Add a flirty touch styled with a fitted sweater or a breezy blouse. For extra comfort, go for culottes or paperbag-waist pants over a sleek bodysuit.

4. Outerwear Essentials

Not sure what’s considered an outerwear essential for a dressy casual look? You’ll want blazers to elevate any outfit so you can throw it over a simple t-shirt and jeans. A denim jacket can keep things cool and laid-back, while a trench coat offers timeless sophistication. Get that cozy-chic vibe with a knit cardigan over a fitted top and midi skirt. Add a little attitude with a leather jacket to balance out more feminine pieces.

5. Cute Shoes

Cute shoes can elevate any dressy casual outfit, so consider stylish sneakers for a more laid-back look or stilettos for an instant touch of glamour. Loafers and ballet flats are great options for something classy to wear with jeans or midi skirts. Play up the glam with block sandals, or go bold with ankle boots and cropped pants. Don’t sleep on mules: they’re the ultimate slip-on shoe for any Avaraista on-the-go for effortless style.

6. The Right Accessories

Add a few magic touches to your dressy casual look with the right accessories. Elevate the simplest outfit with bold earrings or a delicate gold necklace. Belts can be cinched around a dress or blazer. A structured handbag is perfect for the office, while a crossbody bag is a practical choice for everyday wear. Tie a silk scarf to your purse for a stylish twist. Hats can take your outfit to the next level, too! Take a look at all of our accessories for mixing and matching because it’s all about having fun with fashion!

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Dressy Casual for Every Occasion

The right types of dresses make styling for any occasion a breeze: Try wrap dresses for lunch, midi dresses for your next date night, and maxi dresses for when you want to live that glamorous life. For a dressy casual day at the office, keep it relaxed yet professional with form-fitting pants, a nice blouse, and block heels with minimal jewelry. Go flirty for your next night out in a midi dress and strappy heels. Opt for trendy jeans and a cute shirt when you’re hitting the town with your girlfriends. 

For your next family gathering, you can’t go wrong with a cozy sweater dress and ankle boots. If you’re jet setting somewhere this season, prioritize comfort by wearing stretchy jeans with a relaxed blazer and fashionable sneaker for that chic yet practical on-the-go style.

1. Dressy Casual at the Office

Any office that has a Casual Friday day is a great opportunity to show off your dressy casual prowess. Begin with form-fitting pants like our Avara Exclusive Mila pants in black. with a classic silhouette — both options are perfectly professional. Pair them with a structured blouse or knit top to get that put-together look. A blazer can elevate your ensemble, but you can swap out a more formal blazer for a stylish cardigan instead if you’re going for a more relaxed look. Keep it classy and comfy with loafers, block heels, or pointed-toe flats. Accessories should be kept to a minimum. Think structured totes and dainty jewelry.

2. Dressy Casual for Date Night

Add a hint of romance to your next date night when you wear a midi dress with heels — instant glam! For something flirty yet comfortable, try dark-wash jeans with a silky top and ankle boots. A wrap dress is always a win since this dress type flatters every body type and moves beautifully. Layer it up with a jacket or a blazer. Keep your date night jewelry simple and add a bold lip color for a little extra flair.

3. Dressy Casual with Friends

The best nights with friends are the ones where you’re busy making memories, so you’ll want an outfit that looks great but feels effortless. Start with skinny jeans like our Becca jeans in a dark wash or our best-selling Kelsey flare jeans in white by KUT from the Kloth paired with a fitted top or cute blouse. Dial up the fancy with a flowy midi skirt and knit top, but keep it comfy by wearing stylish sneakers or mules. Accessorize with layered necklaces and sunglasses for that extra pop. From Sunday brunch to a casual Friday dinner, you’ll look totally put together with just a few simple pieces.

4. Dressy Casual for a Family Gathering

Get comfy at your upcoming family gathering by wearing a sweater dress with ankle boots for something cozy yet polished. Keep things classic by wearing dark denim with a nice blouse. For extra zhuzh, go for a flowy midi skirt with a tucked-in top layered with a structured blazer for warmth and style. Wear fun accessories like a cute headband or statement jewelry.

5. Dressy Casual for Travel

All aboard the dressy casual express! It’s time to learn how to style your dressy casual look for planes, trains, and automobiles. For comfort with a side of chic, wear comfy jeans or leggings paired with a fitted tee and layer with a light jacket for warmth. The forecast can change unexpectedly when traveling, so you’ll want to layer up just in case the weather turns for the worse. When you’re going on a long walk in a new city or just running to catch your flight at the airport, wear comfortable sneakers to get where you need to go.

Dressy Casual Dos and Don’ts

Remember: Mastering the art of dressing dressy casual is all about balancing the different pieces together. Pair structured pieces like a blazer with more relaxed ones — jeans, please! Invest in versatile staples like neutral-toned tops and bottoms. Never underestimate the undeniable power of cute shoes. Keep things chic with thoughtful accessories and well-fitted outfits. 

On the other hand, you don’t want to go too casual, either. Just because it’s dressy casual doesn’t mean you need to break out your college hoodie and that old pair of sneakers you’ve had for too many years. The goal is to look effortlessly put-together so you look and feel totally comfy and confident. Stick to these dos and don’ts so you can be a dressy casual pro in no time.

1. Do: Mix the Right Pieces

What do we mean about mixing the right pieces? Balance out any outfit. A relaxed blouse goes great with more fitted bottoms. A chic dress can be dressed down with sneakers or a denim jacket. Layer statement outerwear with simple accessories so only one piece is the true statement piece. That way, you’ll be polished and ready for any moment.

2. Do: Accessorize Thoughtfully

To accessorize your outfit thoughtfully, consider your base outfit, whether that’s a nice dress or a top and jeans. Layer with an outerwear piece like a denim jacket or cozy cardigan, and then finish off the look with stylish shoes and one statement accessory like our Nadine earrings or Devon headband.

3. Don’t: Overdo It

Keep your outfit simple. Don’t overload on accessories. You should just have one statement piece, whether it’s a pair of bold earrings or a standout jacket. Be sure to balance your dressy casual elements like heels with casual jeans or a structured blazer with laid-back sneakers. Too many layers can overload your look, and clashing patterns distract from your overall outfit.

4. Don’t: Go Overboard with Trends

As tempting as it can be to keep up with each and every passing trend, don’t let them take over your outfit. Stick to one trendy piece like tweed fabrics for loud luxury or a pop of pistachio as a throwback to the early 2010s staples. Avoid mixing extreme styles or too many patterns at once. You want an outfit that feels stylish but still remains totally you. If you’re not sure which trends to start with, check out our best sellers and new arrivals to see what’s on trend.

How to Shop Dressy Casual Pieces at Avara

Shopping for a dressy casual wardrobe at Avara is a total breeze. From flattering dresses to must-have accessories, we have everything you need to get the dressy casual look. Mix and match our trendy yet timeless pieces to complete your outfits. They’re easy to wear, oh-so-fashionable, and versatile for wearing wherever you go.

Get the Dressy Casual Look

We hope you’ve been inspired by our ultimate guide on how to put together dressy casual outfits. Whether you’re dressing up your jeans or layering a beautiful dress, the key is to keep your look balanced and fun. Refresh your wardrobe and create effortlessly stylish outfits. By mixing and matching different pieces and accessories, you can make any dressy casual outfit totally your own. You’ve got this!

 

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