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9 Summer Dresses that are Easy, Comfortable & Versatile

Dresses are so easy to wear, can be light and comfortable and feel perfect for everything from work to a warm summer evening get-together.

Summertime screams for dresses!

Theoretically dresses are an easy solution to getting dressed every morning, but finding the perfect dress can be an exercise in patience and tenacity.

Last winter a client knew her work schedule for the next three months would be more demanding than usual.  The last thing she wanted to think about in the morning was what top went with what pair of pants.  She was getting up at the crack of dawn and would have long days, seven days a week.  She wanted to get dressed in a flash and be out the door AND know that she looked great.  Dresses for her were a blessing.  She had several dresses she rotated regularly and never was there a day she had to worry about what she was wearing.  She just felt pulled together.

What could be more relaxing in the summer than a few beautiful dresses that make your life easy?  But, how do you navigate the world of dresses to find one that suits your personality, body shape and the occasion without taking all summer to find what you want?

After walking the stores (or searching online) looking for dresses with a lot of my clients this spring, I’ve seen everything that’s out there.  Some are too fussy or the pattern is too busy while others are too dressy.  You’ll find some that are shapeless or too short and others that are too sweet—in many styles it is easy to look like you are trying hard to be twelve again (that raised waist line and short full skirt is not a good combination!).

How to Choose a Summer Dress You Love

Before you give up on finding the perfect dress, here are five factors I assess when dress shopping:

  1. Length – so many are many inches above the knee.  Generally speaking a length that hovers right above or just below the middle of the knee is most flattering and can go anywhere.
  2. Sleeve Length — Dress designers must all live in the tropics with no air conditioning because an unreasonable number of dresses are sleeveless.  Cap sleeves are not always the answer since they aren’t usually flattering (hitting the arm at an awkward length).  See if you can find short sleeves or ¾ sleeves or be sure to have a cardigan, jacket or wrap to keep you warm.
  3. Neckline – There’s a trend right now for dresses to have a high neckline.  While this isn’t terrible, it is not always a good look when you put a jacket or sweater over it.  The neckline will buckle, the interesting detail of the dress is obscured as soon as you put something over it, or you look like you are being strangled by the dress!  And, since so many sleeveless dresses are accompanied by a high neckline, this leaves you in a quandary about how to allow the beauty of the dress to be expressed and stay warm.
  4. A-line vs. Straight – Despite the popularity of the television show, Madmen, an inordinate number of dresses still have a straight skirt.  For women with wider hips or thighs this can be so frustrating whereas a simple A-line dress would alleviate the problem in a heartbeat.
  5. Prints vs. solid.  Not only do you have to find a color that is flattering, but so many dresses have a print or pattern and some of them are pretty wacky!  It is very important to hold out for a print that works for you whether it’s geometric, floral, digital, watercolor, stripes…just to name a few.

Rather than leaving you to wade through the jungle of dresses out there, here are some of my favorite looks that work for a lot of women.

Dresses for Work

While wearing dresses to work in the summer can feel cool and easy, they aren’t always a breeze to find!  Here are three that are super versatile.

Sleeves, please:  This one, by Donna Ricco, actually has a flattering ¾ sleeve and v-neck (you can always wear a lightweight navy cami under it if it comes too low.  The colors are generally flattering and the pattern is understated enough to look good on a lot of women.  And, you can have fun accessorizing it to suit your personality and your office environment.

Work dress Donna Ricco

The Elusive A-line:  Especially when it comes to the office, A-line dresses are hard to find.  This one is a simple style that can easily be office appropriate with a simple short cardigan or jacket in black, white or even a color like a mid-toned pink or muted teal.


Talbots A-line dress

A Summer Staple:  This dress can easily go to the office.  Of course, the color is intense so it will be overpowering on many women (it works well on the model so if you have similar coloring go for it) and the beige/black color option is very difficult to wear without completely disappearing.

Shirt Dress Talbots

Dresses for Casual

When it comes to casual, you want to be able to move freely, feel comfortable, look great and get dressed with ease.  These three dresses offer all of those things.

Long is so easy: A maxi-dress is a delicious way to look feminine and feel comfortable in the summer.  You don’t have to worry about your legs showing and if you add a simple flat sandal you’ll look great.  These colors are beautiful on many women.  And, if you are petite, you can still wear a maxi like this because it creates a long vertical line: Maxi Dress Pyramid

Flirty: If you look at this style on the hanger it looks like it wouldn’t work on anyone.  But, surprisingly, it looks great on many body shapes!  The soft tiers ease nicely over hips and tummies and it feels fun to wear.  The dress is made of a casual jersey fabric, so you can even pair it with a pair of flipflops and go to the park with the kids! You can find styles like this with short sleeves and in a maxi-style as well.

Short Tiered Dressbarn Dress

Traditional sundress:  This style looks great on a lot of women and the raspberry pink color is flattering on many skin tones (except for redheads).  The straps are bra-friendly and because it is made from cotton, jersey and spandex you can easily wear it to the grocery store or to a picnic.

Dress Dolce_Vita

Dresses for a Summer Garden Party

There is nothing as delicious as a summer garden party with the warm air giving way to a balmy breeze.  Yum!  So, what you wear should have the same delicious feel.

Versatile: This is an easy dress to dress up or down depending on how you accessorize it.  If the party is summer casual, wear a pair of flat sandals and fun earrings and you’re all set.  If it’s a bit dressier (or you just feel like being dressier!), wear a fun heeled sandal and a sparkly or statement necklace.

Garden Dress WHBM

Summer Elegance: When I was recently pre-shopping for my New York City client, Heather Dominick, I saw this dress on the rack at Lord & Taylor and HAD to show her.  I could picture her wearing it at a seaside vacation, to a summer wedding or having dinner with her husband at an outdoor café in New York City.  Since one of her four inner beauty words is ‘elegant goddess,’ this dress says it all!

Heather Shopping Long Dress 2014

She looks gorgeous AND she can always decide to cut the dress to knee length and make it even more versatile if she tires of it being long.

Vintage: Love a retro look?  Then you’re in luck because vintage garden party dresses are all the rage.  You can’t beat this look!  The background turquoise is a complimentary color on so many skin tones and the flowers are a mix of pink, peach and watermelon—something for everyone.  The fit and flair style minimizes hips, thighs and a tummy.   Available in sizes xs to 5xl:

Vintage Garden Party Dress

With the entire summer still ahead of us, now is the perfect time to add a dress or two to your warm weather wardrobe.  Find what inspired you above and keep those ideas fresh in your mind as you shop.  Which style speaks to you most?  Please comment and share below.

Note: All styles pictured here are vegan-friendly (made from fabrics that didn’t harm any animals).


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Ginger Burr is a fashion stylist and personal shopper serving clients worldwide from metro Boston.