5 Casual but Cute Outfits Because You Never Know Who You Might Run Into

This means I can wear a hoodie, right?

New York Fashion Week - Street Style - Day 5
Getty ImagesChristian Vierig

You've seen the movie: Recently single heroine sees ex with new girlfriend in the grocery store. Heroine ducks behind a display of cereal boxes, because being single is a weird, new feeling; it makes you wear your pajamas all day while eating ice cream straight out of the quarter-size container. I'm 90 percent sure this was a scene out of How to Lose a Guy in 10 Days... Anyways, these types of situations do happen IRL—like when you happen upon your new boss on your way to Sunday Funday, or are seated next to your frenemy at a mutual acquaintance's dinner party—and when they do, it's best to be armed with a cute outfit. Here, 5 dressed-down outfits that are presentable enough for any type of encounter.

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Dress Up Your Jeans

The phrase "casual and cute" signals to me that the look took less than five minutes to put together. First you'll need jeans because they go with everything. Second, you'll need a v-neck or crewneck tee of your choice. To take this plain outfit from drab to fab, focus on the outerwear: Cover up with a blazer for a hint of sophistication and, if your outfit is lacking color, add in a bright pair of earrings or floral boots. The beauty of this ensemble is that it combines all your basic pieces together to form a fresh new look.

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Tibi plaid blazer, $895

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Madewell black tee, $19

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Banana Republic girlfriend jeans, $55

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Uncommon Matters earrings, $273

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KG Kurt Geiger floral ankle boots, $115

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Reach for Your Hoodie

Hoodies are cozy, warm, comfortable—they're amazing. I wear one at work when the AC is blasting, I lounge in one while watching The Real Housewives of Beverly Hills reruns on Sundays, and I definitely have hoodies in at least five different colors.

If you thought this casual piece was reserved for lazy days only, however, you're wrong. A simple way to elevate said hoodie is with a pair of sleek trousers (bonus points if they're silky) and kitten heel mules. The polished-ness of your pants will balance out the relaxed feel of your hoodie. If you think the outfit's still missing something, layer on accessories like a cool belt or designer bag.

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Diane von Furstenberg cropped hoodie, $155

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Juicy Couture striped pants, $108

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Schutz, $180

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Street Style: June 19 - Milan Men's Fashion Week Spring/Summer 2018
Christian Vierig
Turn Couch Sweats Into Going-Out Pants

If you associate the word "casual" with sweatpants, same. Thanks to the rise of athleisure, there now exist stylish pairs you can leave the house in. Draw inspiration from this fashion week-goer and pair your sweats with a classic button-down. The juxtaposition between loungewear and 9-to-5 work top gives you that effortless, I tried (but not too hard) look. For an extra dose of comfort, style your outfit with sneakers.

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Aritzia button-down shirt, $65

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Vetements sweatpants, $880

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Jules Smith choker necklace, $100

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Vans sneakers, $60

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New York Fashion Week - Street Style - Day 6
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Shine the Spotlight on Your Shoes

If you own a denim jacket, you already have the perfect casual-but-cute piece in your wardrobe. This versatile outerwear works with spring dresses, chunky wool sweaters, ruffle blouses, t-shirts—the list goes on and on. Freshen up your black dress and jean jacket combo with a pair of leopard print boots. Cool footwear is the quickest way to turn your look into a street style hit.

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Ksubi denim jacket, $313

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Felicity & Coco, $98

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Rollie leopard print boots, $180

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Baggu leather tote, $160

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New York Fashion Week - Street Style - Day 3
Getty ImagesChristian Vierig
Go Monochrome

For a cute and casual look that requires minimal effort, wear the same color from head to toe. All-black is typically my go-to, but for a slight twist try, navy or camel (still neutral, more interesting). Take a page out of this street style star's book and build a monochrome outfit out of two pieces: a soft sweater and a pair of sleek trousers. Add a splash of color with your footwear. What appears to be a complicated outfit, will, in reality, take you only minutes to throw together.

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J.Crew tippi sweater, $79

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Tibi wide-leg twill trousers, $174

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Le Specs x Adam Selman sunglasses, $118

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Sam Edelman flats, $56

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