She was looking for fresh outfit inspiration that blends casual comfort with a touch of chic? Whether it’s a stroll in the city or a day on set, Anna Kendrick knows how to make street style look easy. Her looks mix everyday essentials with trendy pieces, showing off her effortlessly cool vibe while staying relatable and stylish.
From bold color choices to laid-back layers, Anna Kendrick’s wardrobe offers a little bit of everything. Each outfit feels carefully curated but never overdone, perfect for busy girls who want to look fashionable without the fuss. If you’re craving outfit ideas that balance practicality with flair, you’re in the right place!
Leather Jacket + Ripped Jeans + Ankle Boots
Anna pairs a rich brown leather jacket with ripped jeans for that perfect blend of cool and casual. The ankle boots give the outfit a chic edge, while her large sunglasses add a touch of streetstyle glam. This look is perfect for running errands or a casual day out, and it gives off a laid-back vibe while staying effortlessly stylish.
Lace Blouse + Denim Skirt + Faux Fur Slides
This outfit is all about contrasts with the delicate lace blouse paired with a casual denim skirt. The faux fur slides add an unexpected, playful twist to the outfit. Anna Kendrick rocks this comfy and cute combination while keeping it practical for a busy day on set. This is a fun take on laid-back yet polished street style, making it perfect for transitional seasons.
Quilted Jacket + Leggings + Running Shoes
Nothing says “on the go” quite like this athleisure-inspired look. Anna opts for a quilted jacket paired with black leggings and grey running shoes, making it a perfect fit for an active lifestyle. Whether you’re out for a jog or just running errands, this outfit is functional and stylish at the same time. Athleisure trends have been huge, and this outfit is ideal for staying fashionable while on the move.
Black Turtleneck + Mini Skirt + Sandals
Anna Kendrick dazzles in this sleek all-black ensemble. The fitted turtleneck complements the mini skirt, which features a subtle pattern. Pairing it with black sandals adds a touch of elegance. This is a great look for evening events or dinner outings. It’s chic, stylish, and comfortable—perfect for making a subtle yet impactful fashion statement.
Floral Skirt + Button-Up Top + Heeled Sandals
In this street-style look, Anna goes for a feminine floral skirt paired with a black button-up top. The heeled sandals elevate the outfit, giving it a dressier feel. This combination is perfect for a casual lunch or day out in the city. The floral print adds a fun, youthful touch, while the black top balances the outfit with sophistication.
Trench Coat + Midi Skirt + Pumps
This is Anna Kendrick showing how to nail a classy fall look. A trench coat paired with a midi skirt and pumps creates a classic silhouette. Perfect for transitioning from a day at the office to an evening out. The neutral tones are easy to mix and match, making this outfit both versatile and timeless.
Striped Polo + Denim Shorts + Sunglasses
For a casual day out on the water, Anna rocks a striped polo tucked into denim shorts. Paired with classic sunglasses, this laid-back outfit is perfect for warm summer days or vacations. It’s simple, comfortable, and effortlessly cool—making it a go-to look for weekend adventures or beach outings.
Red Coat + Striped Top + Skinny Jeans
A bold red coat paired with a striped top and skinny jeans gives off a chic yet relaxed vibe. Anna Kendrick takes a classic color combo and adds her own flair with ankle boots and a crossbody bag. Perfect for colder days when you want to stand out, this look effortlessly blends warmth and style, making it an ideal street style inspiration.
Sheer White Dress + Scenic Vibes
Out in nature, this sheer white dress is all about effortless elegance. With the flowy material catching the wind, Anna Kendrick channels a dreamy, bohemian vibe. This look is great for those relaxed days outdoors where comfort meets style. Ideal for a beach vacation or sunset photoshoot, it captures a carefree, ethereal mood.
White Jacket + Black Skinny Jeans + Burgundy Heels
For a polished yet casual day out, Anna rocks a structured white jacket over black skinny jeans. The burgundy heels add just the right pop of color, elevating this simple yet stylish ensemble. This outfit is versatile for a brunch date or even office errands, proving that basics can still be fashion-forward with the right accessories.
Suede Button-Up Skirt + Textured Top
Suede is having a moment, and this button-up skirt paired with a textured top is a great example. The light neutral tones work beautifully together, creating a subtle but stylish look. Anna Kendrick gives off a laid-back yet sophisticated vibe, making this outfit ideal for transitioning from day to night.
Plaid Coat + Mini Skirt + Nude Heels
This plaid coat paired with a mini skirt exudes fall fashion vibes. With nude heels and a statement mini bag, Anna Kendrick brings a modern twist to classic layering. The plaid pattern adds visual interest, making it a perfect look for a city stroll or casual meetings when you want to look put together without too much effort.
Floral Shirt + Green Ripped Jeans + Tan Tote
Traveling in style, Anna pairs a light floral shirt with green ripped jeans and a tan tote. This look is all about comfort while staying cute, making it a great airport or casual day option. The rolled-up sleeves and sunglasses complete the laid-back, travel-ready vibe, perfect for girls who love to stay on-trend even on the go.
Red Coat + Striped Top + Skinny Jeans
A bold red coat paired with a striped top and skinny jeans gives off a chic yet relaxed vibe. Anna Kendrick takes a classic color combo and adds her own flair with ankle boots and a crossbody bag. Perfect for colder days when you want to stand out, this look effortlessly blends warmth and style, making it an ideal street style inspiration.
Sheer White Dress + Scenic Vibes
Out in nature, this sheer white dress is all about effortless elegance. With the flowy material catching the wind, Anna Kendrick channels a dreamy, bohemian vibe. This look is great for those relaxed days outdoors where comfort meets style. Ideal for a beach vacation or sunset photoshoot, it captures a carefree, ethereal mood.
White Jacket + Black Skinny Jeans + Burgundy Heels
For a polished yet casual day out, Anna rocks a structured white jacket over black skinny jeans. The burgundy heels add just the right pop of color, elevating this simple yet stylish ensemble. This outfit is versatile for a brunch date or even office errands, proving that basics can still be fashion-forward with the right accessories.
Suede Button-Up Skirt + Textured Top
Suede is having a moment, and this button-up skirt paired with a textured top is a great example. The light neutral tones work beautifully together, creating a subtle but stylish look. Anna Kendrick gives off a laid-back yet sophisticated vibe, making this outfit ideal for transitioning from day to night.
Plaid Coat + Mini Skirt + Nude Heels
This plaid coat paired with a mini skirt exudes fall fashion vibes. With nude heels and a statement mini bag, Anna Kendrick brings a modern twist to classic layering. The plaid pattern adds visual interest, making it a perfect look for a city stroll or casual meetings when you want to look put together without too much effort.
Floral Shirt + Green Ripped Jeans + Tan Tote
Traveling in style, Anna pairs a light floral shirt with green ripped jeans and a tan tote. This look is all about comfort while staying cute, making it a great airport or casual day option. The rolled-up sleeves and sunglasses complete the laid-back, travel-ready vibe, perfect for girls who love to stay on-trend even on the go.
