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Easy Summer Outfits Day to Night 2019

I HATE Complicated Outfits, but These Day-to-Night Looks Are So Easy to Wear

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Day-to-night outfits are always spoken about in theory, but when it comes to figuring out formulas that actually transition from the morning to after hours, the challenge is real. For me, common trouble areas include shoes that aren't built for all-day comfort, sneakers or sandals that work for day but feel too casual at night, lightweight pieces of clothing that, while comfortable in the heat, require an extra layer in overactive AC or after sundown, mini accessories that are great for a night out but feel impractical during the day, and casual staples that work for low-key outings but feel a little underwhelming for a dinner, drinks, or a party.

An obvious solution to these dressing conundrums is changing at some point during the day, but I live in New York City and rarely have an opportunity to switch out a piece of my outfit let a lone do a full-on wardrobe change without lugging around an overstuffed tote bag (not exactly chic). I also hate overcomplicated outfits that require too many pieces, which means I have to think super creatively to land on a formula that feels just right (a real Goldilocks predicament, if you will).

If you, too, struggle with day-to-night outfits that actually work day to night, ahead, I've put together 8 Summer formulas that can truly do both. From top-and-skirt combos to all-in-one jumpsuits and versatile dresses, these outfits are not only easy to wear and but star affordable clothing from the POPSUGAR collection at Kohl's. That's what I like to call a win-win.

Image Source: POPSUGAR at Kohl's / Matthew Kelly

1. Day-to-Night Outfit Formula: A Breezy Dress + Denim Jacket

Breezy dresses — like this POPSUGAR Button-Front Dress ($37, originally $50) which is also available in Plus Size — are perfect for a day in the sun while a white denim jacket is the perfect transition piece whether you're in and out of AC or dealing with a post-sunset chill. Woven sandals with a block heel and a canvas bucket bag are the ultimate Summer accents that are both comfortable and practical all day long. Modern pearl earrings make a for darling finish.

Image Source: kohls.com
POPSUGAR Button-Front Dress
$37
from kohls.com
Buy Now

2. POPSUGAR Denim Cropped Jacket

POPSUGAR Denim Cropped Jacket ($32, originally $64)

Image Source: kohls.com
POPSUGAR Denim Cropped Jacket
$32
from kohls.com
Buy Now

3. Pull&Bear Natural Jute Mid-Heel Sandals

Pull&Bear Natural Jute Mid-Heel Sandals ($50)

Image Source: pullandbear.com
Pull&Bear Natural Jute Mid-Heel Sandals
$50
from pullandbear.com
Buy Now

4. Staud Bissett Leather-Trimmed Canvas Bucket Bag

Staud Bissett Leather-Trimmed Canvas Bucket Bag ($295)

Image Source: Net-a-Porter.com
Staud Bissett Leather-Trimmed Canvas Bucket Bag
$295
from net-a-porter.com
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5. Donni June White Pearl Drop Earring

Donni June White Pearl Drop Earring ($134)

Image Source: shopdonni.com
Donni June White Pearl Drop Earring
$134
from shopdonni.com
Buy Now

6. Day-to-Night Outfit Formula: A Camisole + Printed Shorts

On a weekend day or for holiday, a camisole like this POPSUGAR V-Neck Cami ($18, originally $36) is comfy and cute with just about any bottom from jeans to skirts. For a bit of interest, pair this chambray style with printed shorts and finish the look with lace-up sandals, a bright mini bag, and dainty gold rings for day-to-night ease.

Image Source: kohls.com
POPSUGAR V-Neck Cami
$18
from kohls.com
Buy Now

7. POPSUGAR Printed Pull-On Shorts

POPSUGAR Printed Pull-On Shorts ($33, originally $44)

Image Source: kohls.com
POPSUGAR Printed Pull-On Shorts
$33
from kohls.com
Buy Now

8. Massimo Dutti Tubular Flat Sandals

Massimo Dutti Tubular Flat Sandals ($110)

Image Source: massimodutti.com
Massimo Dutti Tubular Flat Sandals
$110
from massimodutti.com
Buy Now

9. Urban Outfitter Super Mini Trapezoid Crossbody Bag

Urban Outfitter Super Mini Trapezoid Crossbody Bag ($24)

Image Source: urbanoutfitters.com
Urban Outfitter Super Mini Trapezoid Crossbody Bag
$24
from urbanoutfitters.com
Buy Now

10. The Last Line Three Set Dainty Gold Band

The Last Line Three Set Dainty Gold Band ($189)

Image Source: thisisthelast.com
The Last Line Three Set Dainty Gold Band
$189
from thisisthelast.com
Buy Now

11. Day-to-Night Outfit Formula: A Feminine Tee + Jeans

You can't go wrong with a t-shirt and jeans during the day and this POPSUGAR Ruffle-Sleeve Tee ($22, originally $30) is a fresh and feminine version that's ultra-lightweight in the heat. To give this simple combo and fashion-forward spin, a colourful bag and heels make for a standout look that's as perfect for a lunch outing as it is for dinner and drinks. Statement earrings are the ultimate finish.

Image Source: kohls.com
POPSUGAR Ruffle-Sleeve Tee
$22
from kohls.com
Buy Now

12. POPSUGAR Straight-Leg Midrise Jeans

POPSUGAR Straight-Leg Midrise Jeans ($25, originally $50)

Image Source: kohls.com
POPSUGAR Straight-Leg Midrise Jeans
$25
from kohls.com
Buy Now

13. A New Day Kayce Strappy Stiletto Heeled Pumps

A New Day Kayce Strappy Stiletto Heeled Pumps ($30)

Image Source: target.com
A New Day Kayce Strappy Stiletto Heeled Pumps
$30
from target.com
Buy Now

14. Emily Levine Dumpling Knotted Floral-Print Cotton-Voile Tote

Emily Levine Dumpling Knotted Floral-Print Cotton-Voile Tote ($145)

Image Source: Net-a-Porter.com
Emily Levine Dumpling Knotted Floral-Print Cotton-Voile Tote
$145
from net-a-porter.com
Buy Now

15. Corita Mambo Earrings

Corita Mambo Earrings ($78)

Image Source: shopcorita.com
Corita Mambo Earrings
$78
from shopcorita.com
Buy Now

16. Day-to-Night Outfit Formula: A Linen Dress

Is there anything better than a linen dress in the Summer? This POPSUGAR Button Up Midi Dress ($45, originally $60) is a flattering silhouette on all body types and feels quintessentially Summer with white sandals, a unique basket bag, and colourful drop earrings.

Image Source: kohls.com
POPSUGAR Button Up Midi Dress
$45
from kohls.com
Buy Now
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17. Journee Collection Colette Sandals

Journee Collection Colette Sandals ($42, originally $49)

Image Source: kohls.com
Journee Collection Colette Sandals
$42
from kohls.com
Buy Now

18. Ulla Johnson Raya Trapeze Bag

Ulla Johnson Raya Trapeze Bag ($295)

Image Source: shopbop.com
Ulla Johnson Raya Trapeze Bag
$295
from shopbop.com
Buy Now

19. Sophie Monet Wood & Jade Aurora Drop Earrings

Sophie Monet Wood & Jade Aurora Drop Earrings ($150)

Sophie Monet Wood & Jade Aurora Drop Earrings
$150
from sophiemonetjewellery.com
Buy Now

20. Day-to-Night Outfit Formula: A Cute Tank + Colourful Skirt

Up the ante of your standard tank top-and-miniskirt combo with bright colours and playful prints. This POPSUGAR Smocked Tank Top ($27, originally $36) makes a splash when paired with a yellow skirt and feels especially fashion-forward with trendy (and comfortable!) kitten heels, a minimal woven bag, and a cute anklet.

Image Source: kohls.com
POPSUGAR Smocked Tank Top
$27
from kohls.com
Buy Now

21. POPSUGAR Button-Up Mini Skirt

POPSUGAR Button-Up Mini Skirt ($37, originally $50)

Image Source: kohls.com
POPSUGAR Button-Up Mini Skirt
$37
from kohls.com
Buy Now

22. Zara Pleated Mid-Height Heeled Sandals

Zara Pleated Mid-Height Heeled Sandals ($40)

Image Source: zara.com
Zara Pleated Mid-Height Heeled Sandals
$40
from zara.com
Buy Now

23. Hunting Season Trunk Mini Raffia and Leather Shoulder Bag

Hunting Season Trunk Mini Raffia and Leather Shoulder Bag ($395)

Image Source: Net-a-Porter.com
Hunting Season Trunk Mini Raffia and Leather Shoulder Bag
$395
from net-a-porter.com
Buy Now

24. Ariel Gordon Figaro Anklet

Ariel Gordon Figaro Anklet ($170)

Ariel Gordon Figaro Anklet
$170
from arielgordonjewellery.com
Buy Now

25. Day-to-Night Outfit Formula: A Printed Jumpsuit

Take your jumpsuit — like this POPSUGAR Wrap Jumpsuit ($34, originally $68) — from work to drinks by teaming yours with sleek mules, a woven shoulder bag, and gold hoops. The result is polished yet playful.

Image Source: kohls.com
POPSUGAR Wrap Jumpsuit
$34
from kohls.com
Buy Now

26. & Other Stories Criss Cross Tortoise Buckle Mules

& Other Stories Criss Cross Tortoise Buckle Mules ($129)

Image Source: stories.com
& Other Stories Criss Cross Tortoise Buckle Mules
$129
from stories.com
Buy Now

27. Cult Gaia Kaia Bag

Cult Gaia Kaia Bag ($298)

Image Source: shopbop.com
Cult Gaia Kaia Bag
$298
from shopbop.com
Buy Now

28. Laura Lombardi Duo Earrings

Laura Lombardi Duo Earrings ($92)

Image Source: lauratlombardi.com
Laura Lombardi Duo Earrings
$92
from lauratlombardi.com
Buy Now

29. Day-to-Night Outfit Formula: A T-Shirt + Shorts + Cardigan

For coastal activities from beach days to sailing and strolling the main street, a comfortable t-shirt like this POPSUGAR Babydoll Swing Tee ($22, originally $30) is idyllic with a cute pair of shorts. When the chill sets in, a striped cardigan is key to have on hand while lace-up espadrilles, a leather-and-straw bag, a chainlink necklace give this look an elevated, fashion-girl effect.

Image Source: kohls.com
POPSUGAR Babydoll Swing Tee
$22
from kohls.com
Buy Now

30. POPSUGAR Printed Pull-On Shorts

POPSUGAR Printed Pull-On Shorts ($33, originally $44)

Image Source: kohls.com
POPSUGAR Printed Pull-On Shorts
$33
from kohls.com
Buy Now

31. POPSUGAR Nautical Cardigan

POPSUGAR Nautical Cardigan ($25, originally $50)

Image Source: kohls.com
POPSUGAR Nautical Cardigan
$25
from kohls.com
Buy Now

32. Mango Laces Slingback Espadrilles

Mango Laces Slingback Espadrilles ($60)

Image Source: shop.mango.com
Mango Laces Slingback Espadrilles
$60
from shop.mango.com
Buy Now

33. Hereu x Net Sustain Alqueria Leather-Trimmed Woven Straw Tote

Hereu x Net Sustain Alqueria Leather-Trimmed Woven Straw Tote ($240)

Image Source: Net-a-Porter.com
Hereu x Net Sustain Alqueria Leather-Trimmed Woven Straw Tote
$240
from net-a-porter.com
Buy Now

34. Uno de 50 Chain 6 Gold

Uno de 50 Chain 6 Gold ($120)

Image Source: unode50.com
Uno de 50 Chain 6 Gold
$120
from unode50.com
Buy Now

35. Day-to-Night Outfit Formula: An Eyelet Top + Jeans

Another fresh alternative to a t-shirt and jeans is an eyelet top like this POPSUGAR Eyelet Tee ($33, originally $44) with true-blue denim. Bright block-heel sandals, a minimal bag, and a chainlink bracelet take this combo from simple to sophisticated.

Image Source: kohls.com
POPSUGAR Eyelet Tee
$33
from kohls.com
Buy Now

36. POPSUGAR Straight-Leg Midrise Jeans

POPSUGAR Straight-Leg Midrise Jeans ($25, originally $50)

Image Source: kohls.com
POPSUGAR Straight-Leg Midrise Jeans
$25
from kohls.com
Buy Now

37. Charles & Keith Yellow Mesh Mini Block Heel Sandals

Charles & Keith Yellow Mesh Mini Block Heel Sandals ($69)

Image Source: charleskeith.com
Charles & Keith Yellow Mesh Mini Block Heel Sandals
$69
from charleskeith.com
Buy Now

38. Medea Prima Short Small Leather Tote

Medea Prima Short Small Leather Tote ($440)

Image Source: Net-a-Porter.com
Medea Prima Short Small Leather Tote
$440
from net-a-porter.com
Buy Now

39. Gorjana Parker Bracelet

Gorjana Parker Bracelet ($60)

Image Source: gorjana.com
Gorjana Parker Bracelet
$60
from gorjana.com
Buy Now

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