My Summertime Dress-Buying Philosophy

Jul 10, 2019

I have a simple plan when it comes to summertime dressing: Buy dresses that look more expensive than they are, wear them til they fall apart, repeat.  I hunt for dresses that will draw compliments, that I can dress up or dress down.  Here are a few dresses to boost your wardrobe, and tips for how to spot them.

Whether it’s a work dress or a casual dress I want impact that outpaces the price.  When people ask who made my dress, I want the to be shocked when I say where I got it.  Think of it like a shopping Easter Egg Hunt.

Earlier this year, I bought an eyelet wrap dress at H&M that has since sold out.  Every time I wear it, I get “Cute dress” and “Love the dress” as I walk down the street.  It’s breezy, cute, and looks like I spent a fortune when I spent $99.

This eyelet dress also from H&M is a close cousin to the one I bought.  It has the same summery feel, and the same easy sophistication.  H&M also has this $49 eyelet off-the-shoulder dress and this pretty yellow puff-sleeve dress for $99.

Plus-size?  This J.Crew dress is a great option.  I also love this Calvin Klein dress in white.

Now, what drew me to these three dresses.  Eyelet is a great, feminine material for summer dresses.  It always feels pretty and a little fancy.  The styling is inspired by pricier brands like Alexis and Zimmermann.  And the dresses are versatile — casually you could wear them with dry-shampoo-hair and a flat sandal, for a nicer occasion, you could lift them with a tan block-heel sandal and a statement earring.

This dress from Ecowish ($35) is a great option for weekend or casual weddings.  It comes in black, white, or a breezy blue color.  The ruffle shoulder keeps it from being boring, the a-line skirt is flattering on almost anyone, and like the H&M dress, it’s easy to dress up or down.  I bought this dress last week, wore it once, got stopped three times to ask where I got it.

Okay, let’s talk about a semi-casual work option. This Donna Morgan Dress ($39) is one I have in two colors.  The fit-and-flare shape is feminine and a little relaxed.  Also, a sleeve.  Heaven knows, I love a sleeve.

While they’re not the most exciting brands in the world, Donna Morgan, Adrianna Papell, and other department store brands are the most reliable options.  If you want to find these brands at more affordable prices, Nordstrom Rack is my first choice.

Plus-size?  I really like this Kimono Sleeve Dress from Eloquii.  It’s a good color, with fun details.

As for what to look for, I always want knee-length, some kind of sleeve, and a heavy-ish fabric.  These qualities make the dresses wearable, but they also make them look more expensive than they are.

What do you look for in a summer dress?  And what are your best dress-shopping tips.

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  1. Lisa says:

    How would you style the Donna Morgan dress? I bought it when you first posted it and have had trouble figuring out how to wear it for work. Thanks!

  2. strin012 says:

    The Easter Egg Hunt philosophy is honestly how I shop most often. I go places like Nordy Rack and Dillard’s clearance centers and shift through a lot of things I’d never wear, but so often find affordable gems that I keep for years. It’s pretty rare that I search for something very specific, even staples, as I generally keep an eye out for staples on sale, even when I might not be ready quite yet to replace one.

  3. Sarah says:

    This dress is on repeat for me this summer. I got it in petite and it fits like a dream. Not too short and not too long. At my age, I am over mini dresses, but I hate maxis. I got it on sale for $17.50 and have it in red and navy polka dot. It is easy to dress up or down and it is a weekend staple for me. I get tons of compliments.

    https://oldnavy.gap.com/browse/product.do?pid=416590032#pdp-page-content

  4. Denise says:

    It’s ‘summer’ for about 6-7 months straight in Houston, ha ha. I find I adopt far less restrictive clothing just due to sheer necessity in super high temps

    I opt for sleeveless dresses, because sweat will happen, and your sleeved dresses will get pit odor / stain which will triple your dry cleaning bill

    No dresses with belts. No pencil skirts. definitely no skinny jeans. Nothing that ‘clings’ to the skin or waistline because that’s uncomfortable when you’re melting. No wool!

    Outside of dresses I wear nd loose skirts with a little volume, midi length but light. My favorite summer dress is a black eyelet sleeveless A-line that I picked up for next to nothing at Ann Taylor a couple of years ago. If I must wear slacks, I keep the tops long enough to cover the waistline which eliminates the need for a belt. And its important that the tops be somewhat flowy and machine washable.

    The life of a professional living in a swamp… 😉

    • Janine says:

      Houston probably wins over DC in terms of swamp-like conditions, but I don’t find much difference in sweat odor between sleeveless and short-sleeved dresses for work. It could be because I don’t spend much time outside in work dresses, other than a short commute or to head outside at lunch.

      I wanted to comment to say that I am wearing a dress today that is the product of both this blog and reader comments! I have been reading the blog for awhile and have long agreed with your preference for short-sleeved dresses (and shirts) in order to save my blazers and, when not wearing one, to keep my shoulders professional and warm in chilly A/C. Based on some reader comments about the washable Ann Taylor suiting, I snapped up a short-sleeved navy dress on sale a few weeks ago and love it. My summer work dress uniform is pretty simple – short-sleeved, structured dresses in a variety of neutral and bold colors. For casual dresses, I have been living in colorful maxi dresses this summer. Love the idea of buying dresses that look more expensive than they are.

    • Julia says:

      Excellent description of Houston summer weather and strategies for clothes.

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