9 New Outfits to Try If You're Overwhelmed by the Concept of Dressing Up Again

Earlier this year, I realized that I'd become less savvy at quickly putting together a cool outfit. I think this is mainly because I'd kind of forgotten what clothes I own (aside from comfy lounge ones, of course). Just like any skill, the ability to put together a good outfit can get a little rusty without practice. When you spend many months just deciding which matching sweatsuit to wear with which slippers, that's enough to throw anyone out of outfit-planning practice.

As vaccination rates have thankfully increased in the U.S. over the past couple of months, venturing back out into the world is something many of us have started to be able to do, and I think we've all come to realize that we need outfits to do so. If—on top of everything else—that has you feeling overwhelmed, I 100% get it. So I took some time to search for easy outfit ideas that are a bit dressed up, but not in a complicated way. Read on to steal them for your own outfit arsenal this spring and summer and to shop pieces that capture the vibe of each outfit.

casual-cool-summer-outfits-293102-1620330486137-image

Short-Sleeve Button-Down + Pleated Trousers + Flats
(Image credit: @tylynnnguyen)

This back-to-business look is chill enough to wear pretty much anywhere.

Shop the Vibe

casual-cool-summer-outfits-293102-1620330476663-image

Cardigan + Slip Dress + Kitten Heels
(Image credit: @tamaramory)

A dress and heels may seem intimidating, but not when the dress is comfortable and the heels are low.

Shop the Vibe

casual-cool-summer-outfits-293102-1620330489430-image

White Dress + Socks + Sneakers
(Image credit: @champagnemani)

You can't go wrong with a midi dress and sneakers, especially when those sneakers are New Balances and are styled with socks.

Shop the Vibe

casual-cool-summer-outfits-293102-1620330478173-image

Tank Top + Printed Pants + Loafers
(Image credit: @emnitta)

Take a break from jeans and opt for a pair of flowy printed pants paired with low-key items (e.g. a tank and loafers).

Shop the Vibe

casual-cool-summer-outfits-293102-1620330490171-image

Tiered Dress + Platforms Sandals
(Image credit: @alyssainthecity)

Dare I say this two-piece outfit is even easier to throw on than a sweatsuit and slippers?

Shop the Vibe

casual-cool-summer-outfits-293102-1620330483010-image

Cardigan + Knit Pants + Retro Sneakers
(Image credit: @chloepierreldn)

This comfortable outfit is perfect for travel days, errand days—you name it.

Shop the Vibe

casual-cool-summer-outfits-293102-1620330484697-image

Tube Top + Jeans + Heels
(Image credit: @jennymwalton)

Remember jeans? This is exactly how to wear them out at night this summer.

Shop the Vibe

casual-cool-summer-outfits-293102-1620330486607-image

Ruched Top + White Pants + Sandals
(Image credit: @vikilefevre)

A cool ruched top in a pretty hue is the perfect counterpart to a pair of utilitarian pants.

Shop the Vibe

casual-cool-summer-outfits-293102-1620330488333-image

Tennis Dress + Chic Accessories
(Image credit: @cassdimicco)

Might as well embrace the crisp tennis look while it's still trending. Just be sure to pair it with chic accessories so that it doesn't look like you're actually heading to a match.

Shop the Vibe

Next up, The Summer Shirt Style Every Fashion Girl Owns in Multiples

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.