I’ve always been someone who is overdressed for occasions and will always err on the side of dressing up a bit more rather than dressing down. Even my casual outfits tend to look more elevated because I love to add extra touches to style them in a more put together way. That could mean adding certain accessories, doing my hair/makeup or ensuring all the pieces are free of wrinkles or creases. I feel my best when my outfit is well thought out and put together and it can definitely create a good impression when meeting people for the first time. I’ve had questions over the years about how to look dressy without dedicating a ton of extra time and energy to it which is possible but does require a bit of planning. I am strategic when buying new items for my closet making sure I choose pieces that are easy to style, fit well and can be worn over and over. And accessories may seem like an afterthought but they can truly take an outfit from casual to dressy in a second. Here’s a roundup of dressy outfits that will keep you looking chic all summer long!

How To Look Chic This Summer – 10 Dressy Outfits For Women

Black Midi Dress with Rattan Bag

Dress | Cardigan | Shoes | Bag | Sunglasses

Most of my closet is neutral tones and that is definitely a conscious choice. Neutral items are easier to style (in my opinion) and can alleviate the stress of wondering if all the colors in your outfit are working well together. A black midi dress is something that can be worn with virtually any accessories so there are endless ways to style it. I bought this rattan bag nearly 7 years ago when it was SUPER popular and though the buzz surrounding it has died down, I still wear it every single summer. It’s a unique shape yet looks great with all my spring and summer looks.

Short Sleeve Shirt Dress with Scalloped Hem

Dress | Bag (code: MAREE15) | Shoes (similar) | Sunglasses

Dresses are always an easy option for summer to instantly look dressy with little to no effort. And a shirt dress has the ability to be dressed up or down so it’s a timeless style that you can rely on year after year. The reason I chose this dress as a perfect “dressy outfit” option is the added scalloping and eyelet detail near the hem. Those extra details add something to this dress which instantly elevates it no matter how it is styled.

All White Outfit with Neutral Accessories

Sweater | Jeans | Belt | Shoes | Bag | Sunglasses

An all-white look for summer is something I go back to year after year because it always looks chic. Once again I’ve kept the accessories neutral though not necessarily all matching in exact tones. You can definitely choose beiges or browns in the exact same shade but I personally like to mix different ones together to give the all white outfit a bit more interest.

Wide Leg Jeans with Chic Accessories

Tank | Jeans | Belt (code: MAREE20) | Sandals | Bag (similar) | Sunglasses

In its truest form, this casual outfit is just jeans and a t-shirt. But adding the right accessories and ensuring your clothing fits well (not too oversized or too tight), a simple jeans/t-shirt look can be dressy. I have actually come to think of a wide leg jeans outfit as more elevated than a look with tighter or more fitted jeans. And even if you don’t want to wear heels, choose a more structured flat sandal over rubber flip flops or athletic sneakers.

Tailored Shorts with a Vest

Vest | Shorts (similar) | Sandals | Bag

You may not think of shorts as a dressy option but this outfit is a perfect example of how the right type of shorts can really look polished. Choose a longer style pair of shorts in a crepe fabric that have a trouser like fit to them. Though the fit is loose, the waist is usually a bit more fitted and creates a more business casual/professional look than a regular pair of shorts. I was never a huge fan of shorts until I found a style like this. They are super comfortable but still look more put together.

Belted Shirtdress in a Bold Color

Dress | Bag (code: MAREE15) | Shoes (similar) | Sunglasses

Another example of how a shirt dress really can look dressy with little to no styling. This dress has been a top seller with my readers for nearly a year and I personally find it to be one of my most worn dresses. The fabric is stiff and has a slight sheen to it which instantly elevates the outfit. I usually choose neutral accessories to wear with it and it’s an outfit I don’t put a ton of effort into styling. The dress IS the outfit.

Striped Tank Midi Dress with Neutral Shoes

Dress | Bag | Belt | Shoes (similar) | Sunglasses

Stripes are one of the safest prints to wear because it’s always in style and automatically looks dressy in regards to certain clothing styles. A striped midi dress like this one has a classic look to it and even styled with sneakers and a casual bag, it would still have an elevated dressy vibe. Also consider the fabric of certain items when shopping because certain fabrics can look dressier than others. This particular dress is a heavier stretch fabric so it holds it shape nicely.

Cardigan Set with Wide Leg Jeans

Cardigan | Tank | Jeans | Belt (code: MAREE20) | Shoes | Bag | Sunglasses

Mixing prints can be a bit daunting but when purchasing a set that already mixes them for you is an easy way to do it effortlessly. I love the look of this cardigan and tank that are meant to be worn together but can also be styled separately. I wore the same cardigan in a few photos above with the black midi dress. And if you are hesitant about trying wide leg jeans this is a great pair that has a slim fit through the hips and a slight wide leg without being too loose. There is something about wide leg jeans and trousers that does instantly make the outfit appear dressier without adding anything extra. I like to have my jeans/pants come just below my ankle so that I can wear flats or heels with them but they don’t drag on the floor. Overly long pants are having a moment right now but I find they can easily look messy so I choose a safer option with a length that always looks polished.

Wide Leg Linen Pants and a Fitted Tank

Tank (similar) | Pants (similar) | Shoes | Bag (similar) | Sunglasses

Here is another great look with wide leg pants instead of jeans and I love how comfortable they are while still looking dressy. Linen is a tricky fabric because it can become wrinkled as the day goes on so it’s a good idea to ensure the item fits well and try to add some nice accessories which will offset a bit of wrinkled look that will be inevitable. At the end of the day, we still have to live and move around in our clothes so they will show signs of wrinkling and creasing which IS OK! Linen is also incredibly lightweight and comfortable to wear during the summer so I will sacrifice some wrinkles in order to not overheat. LOL

White Linen Blouse with a Denim Midi Skirt

Shirt (similar) | Skirt (similar) | Sandals | Belt | Bag (similar) | Sunglasses

This outfit is a perfect example of how accessories can instantly elevate a look. A linen shirt and denim skirt are fine together but adding the black belt, black bag and simple strappy black sandals makes this outfit look more styled and dressy. Adding these extra touches are what can take your outfits from boring to instantly polished. You may notice that I have also worn these accessories with a few other outfits in this post so this helps explain my statement about being intentional with my purchases. I want to find items that be worn with various outfits and looks.

How To Make Casual Clothes Look Dressy

Add accessories – adding a belt or jewelry can immediately elevate a look

Steam all your pieces – be sure to give a quick steam to all your pieces before you wear them. Wrinkles can make or break an outfit.

Focus on fit – if something fits too tight or too loose, it can really detract from the overall look of an outfit.

Hem anything too long – if pants or jeans are too long, it can make them look messy or ill-fitting. I personally cut nearly all of my jeans leaving a raw hem but if it is pants, I will go have them tailored to a length that works for heels or flats.

Do your hair or makeup – you don’t have to do both, but spending the time to style your hair or add a bit of makeup can instantly make any outfit look dressier.