6 Dresses You Can Wear Anywhere With Heels, Flats, or Boots

When it comes to summer outfits, a dress is probably the simplest way to go. You may love your jeans just as much as the next girl, but you have to admit that sometimes, a breezy one-piece outfit makes for a much more comfortable summer ensemble. The problem with dresses, though, is that they all seem to require different shoes. Wedges, pumps, espadrilles, ballet flats, booties, and sandals: There are tons of options when it comes to footwear, and some dresses just don’t look right unless you wear them with a specific style.

But there are plenty of dresses that will look polished and flattering with many styles of shoes, whether you’re in the mood to wear the same ballet flats that you’ve been wearing day in and day out or get some more use out of the booties that you haven’t worn since late spring. We’ve chosen six dresses that can style with heels, flats, or boots, and wear just about anywhere you need to go this summer. Read on for our top picks.

1. Denim shirt dress

Brooks Brothers denim pullover dress

A denim shirt dress is a more casual take on the trend, and is a lot easier to dress up or down than you might imagine | Source: Brooksbrothers.com

Another variation on the shirt dress — and one you can wear with heels, flats, or even sneakers — is this denim dress from Brooks Brothers. With a half-placket, this is a pullover or popover style, which is super easy to style for the summer. Just add your favorite pair of shoes, and perhaps a belt or a clutch to accessorize, and you can completely change the look day to day.

2. Plaid fit-and-flare dress

Brooks Brothers plaid dress

The fit-and-flare silhouette is a classic for a reason, and this one does a masterful job of showing off a great plaid print | Source: Brooksbrothers.com

If a shirt dress isn’t exactly your style, another classic silhouette that you should try is the fit-and-flare. This silhouette is perfect for showcasing a summery pattern, like the plaid on this Brooks Brothers number. If you keep the length flattering, usually within a few inches above the knee, you can wear heels, flats, or sandals with this style of dress.

3. Gingham fit-and-flare dress

Kate Spade gingham fit and flare dress

For a sundress you’ll want to wear again and again, choose a flattering fit-and-flare silhouette and a crisp cotton gingham | Source: Nordstrom.com

For those who love sundresses, Kate Spade’s gingham fit-and-flare dress is a great style to try. Constructed of crisp cotton, this dress will look great styled with pumps and a cardigan for the office or paired with a simple sandal for running errands. And when the weather cools down, you can add a light jacket and a pair of ankle boots to get even more mileage out of the style.

4. Striped dress

Kate Spade striped dress

Three-quarter sleeves offer some protection against over-enthusiastic air conditioning, and stripes keep the look classic | Source: Nordstrom.com

If you’re less of a sundress kind of girl and more interested in a style that’ll keep you from freezing in an over-air-conditioned office, then perhaps a striped dress with three-quarter sleeves would be a better match. This Kate Spade style is a flattering option, with a hemline that will work well with heels, flats, or even your favorite pair of ankle boots.

5. Striped knit dress

Tory Sport striped dresses

Whether you’re traveling or just running errands, wrinkle-proof knit dresses are an easy and comfortable style for summer | Source: Barneys.com

Another easy-to-style silhouette is a form-fitting knit dress. This striped dress from Tory Sport will look great with anything from a pair of polished pumps to your favorite pair of canvas sneakers. This style is also ideal for traveling, since it won’t wrinkle as easily as many other dresses do.

6. Little black shift dress

T by Alexander Wang dress

Every girl needs a little black dress, even for summer, and this style stands out with some unexpected details | Source: Barneys.com

Our final pick for a style that’s easy to wear, plus simple to pair with all of your favorite shoes? A little black dress, of course. We’re partial to this layered style from T by Alexander Wang. Sure, it’s a summer-ready LBD with a great bandeau detail. But its shift silhouette and flattering length make it easy to dress up or dress down, and you’ll be layering with it well into the fall.

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