Shopping·8 min read

The Best Summer Dresses and What to Layer Them With

Design: theSkimm | Photos: Hill House Home
July 12, 2023

Products you buy through our links may earn us a commission. Oh, and if something's out of stock, oops, it was there (and all prices were accurate) at time of publication.

We can all agree the easiest thing to wear to the office during the summer months is a dress. It’s a one-step outfit that’s breezy, comfortable, and layers nicely with a jacket when the office AC is blasting full force.

Need help matching your dress with the right layering piece? We got you. We’ve handpicked dresses you can wear to work, brunch, or while running errands. Add a lightweight jacket, cardigan, or blazer and you’ll be all set for the inevitable change in temperature when you step indoors. Your mornings, hacked.


A tank dress that’s extremely comfortable…

Target forever. Let us put you on to some of the most comfortable clothing we’ve ever put on our bodies, thanks to the ribbed cotton. It’s lightweight and feels like wearing your favorite worn-in tee. It comes in five colors and sizes XS–4X. ($15, Target)

Buy it
Hill House Home

A midi dress that’s giving picnic vibes…

We love a colorful stripe pattern for the summer. With how breezy this dress is, you just can’t go wrong. Wear this with a jacket for work, then shed your outer layer for post-work plans. Win-win. ($150, Hill House Home)

Buy it

A Lucky Brand denim jacket that comes in white…

A crisp white denim jacket always pairs well with a flowy summer dress. This one is made with rayon so it can stretch and move with you. It’s a wardrobe staple and comes in sizes XS–XXL. Customers suggest sizing up for a roomier fit. Psst…how cute would this be over the Target tank dress? ($79.50, Amazon)

Buy it

A black midi dress with a twist…

This midi dress may look ordinary, but thanks to the back cut-out, your waist will be  slightly accentuated. The jersey material, cap sleeves, and breezy skirt are sure to keep you cool. It also comes in a cherry color and sizes XS–XL. ($198, Reformation)

Buy it
J. Crew

A cardigan that can also be worn on its own…

Undo all the buttons on this cardigan, and you’ll have a light overshirt layer. Close them back together and wear it solo when the seasons change and the temp drops a bit. It comes in eight colors and sizes XXS–3X. PS: If you’re looking for a chic pullover option, check this one out. ($79.99+, J.Crew)

Buy it
Abercrombie & Fitch

The perfect strapless dress to take you to after-work drinks…

Strapless dresses are synonymous with summer and rooftops. We don’t make the rules. This one is made of stretchy, breathable satin that’s smocked at the back for a comfortable, snug fit. Add a jacket for the office, then peel it off when it’s shoulder-baring o’clock. It comes in three colors and sizes up to XL. ($57.60, Abercrombie & Fitch)

Buy it

A shirt to pair with any dress for a coastal grandmother moment…

Stun and stay cool when you throw this button-up over any dress. This shirt is slim-fit, so it won’t look overly baggy with an already flowy dress. You’ll find yourself reaching for it to wear with shorts as well. We love the French Blue. Classic for a reason. ($79.99+, J.Crew)

Buy it

A structured sheath dress for a more polished look…

The humble sheath dress is peak professionalism. This one hits just below the knee and has a twist at the shoulder that’ll set it apart. The black is a staple in any wardrobe, and it comes in sizes 14–28. Customers love that the fabric is lightweight but won’t bunch as you wear it. ($49.97, Eloquii)

Buy it

A smocked dress with spaghetti straps…

From the airy fit to the smocked bust to the delicate straps, we foresee this being worn at the office or while out to dinner on vacation. It pairs well with a denim jacket or linen blazer, and comes in sizes XXS–4X. Praise. ($128, Madewell)

Buy it

A summer blazer in a not-so-typical color…

This blazer is made of a lightweight linen, so it won’t make you sticky during your commute. It comes in a delightful pale blue that will go nicely with almost any dress. Plus, it’s machine-washable. Sold. ($178, Everlane)

Buy it

A V-neck slip dress that allows for optimal airflow…

If you wake up feeling particularly fancy, try this minimal (yet eye-catching) slip. It looks great paired with low block heels or flats, and comes in sizes XS–XL. Just pick from nine hues. ($79.90, Quince)

Buy it

A mini dress that’s sure to become your new favorite…

Between the flattering fit, soft jersey knit, and wide range of colors, what’s not to love? The V-neck isn’t too revealing and the fabric will move (but never stretch out). It comes in sizes XS–6X, and customers love that it isn’t too short as it hits right above the knee. ($18.68+, Amazon)

Buy it

A trucker-style denim jacket because it’s important you have one…

The most iconic light layer of all. This one is a little roomier but not too oversized (we recommend sizing up if you want a larger fit). It’s made from 97% cotton and 3% elastane, which means it won’t be so stiff that it requires extensive breaking in. It comes in several washes and sizes XS–4X. Happy layering. ($31.98+, Amazon)

Buy it

Live Smarter

Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.