Shorts are one of my favorite summer staples. In fact, I wear them as long as I possibly can. They’re great for soaking up the much-needed sunshine before winter puts my legs into hibernation.
The one issue I come across finding cute outfits with shorts is dressing them up. Shorts look amazing with any casual top or shoes, but for a night out, things get more complicated.
One of the ways I style my shorts for a dressier look is a french tuck and a pair of heels. Sometimes it all comes down to attitude. If you’re interested in new ways to wear your shorts, check out my fave looks for inspiration.
1. High Rise Cut Offs With White Peasant Top
These light blue distressed cut-offs look so fresh and airy with a white peasant top. The high waist looks amazing with a crop-style top, bearing just a hint of midriff. Buy these shorts at Lulus.
2. Paperbag Linen Shorts With Black Tank
A casual black tank makes these linen paper bag-style shorts stand out. The tan and black retain neutrality, making this a look for casual or dressy wear, depending on the accessories. Buy these shorts at Pink Lily.
3. Brown Vegan Leather Shorts With Mock Turtle Neck and Blazer
The brown vegan leather makes this outfit shine. It’s business casual with an edginess I adore. A tan mock turtle neck and beige blazer tie the look together. Buy these shorts at Lulus.
4. Daisy Yellow Shorts With Matching Puff Sleeve Crop
White cowboy boots and a straw sunhat help these shorts steal the show. Daisy yellow with a matching puff sleeve crop top screams country girl in the city. I’d definitely wear this look. Buy the shorts at ASOS.
5. Pleated Red Paperbag Shorts and White Tank
I’m in love with these pleated paper bag shorts. The texture and volume create a skirt-like effect. Paired with a white tank, it looks like a recipe for Valentine’s Day romance. Buy these shorts at Lulus.
6. Pale Blue Shorts and Vest Set With Black Crop and Sandals
This pale blue short and vest set gives me safari vibes, but in the best possible way. Paired with a solid blank crop top and puff sandals, this outfit easily flips between casual and business casual. Buy these shorts at ASOS.
7. Green Drawstring Lounge Shorts With Matching Ribbed Top
Loungewear never looked so good. These spring green shorts and matching peek-a-boo top are both comfy and chic. Perfect for lounging at the pool or wearing out for lunch with the girls. Buy these shorts at Lulus.
8. Light Wash Denim Overall Shorts and White Long Sleeved Shir
Transitioning to fall is simple with the right shorts. These light wash denim overalls slay with a long sleeve white shirt and plaid button-up tied around her waist. A pink hat and white boots keep things sunny. Buy these shorts at Pink Lily.
9. White on White Shorts and Tied Top
If you’ve got a white party to attend, consider these paper bag shorts and a matching white top. The front tie and billowy sleeves on this top give the look light, airy energy. Buy these shorts at Lulus.
10. Pink Polka Dot Shorts and Taupe Bodysuit
Paper bag shorts look so good with a bodysuit. It accentuates all the right places on any shape. This square-necked taupe bodysuit adds serious feminine energy to pretty polka-dot pink shorts. Buy these shorts at Pink Lily.
11. Casual Chambray Shorts and T-Shirt
These dark blue chambray shorts are keeping it casual. Matched with a cute graphic t-shirt and classic Adidas runners. I love this combination for an afternoon of hometown tourism. Buy these shorts at ASOS.
12. Sage High Waisted Shorts and Ribbed Top
The ruffled sleeves on this ribbed top give these high-waisted shorts a touch of feminine whimsy. I love the color! Sage is so in right now, and it softens the crop top short combo. Buy these shorts at Pink Lily.
13. Brown Shorts and Black Top
The one-sided sleeve top gives this outfit a “devil may care” quality, it would absolutely pass for business casual. I love the softness of these brown shorts. Buy these shorts at ASOS.
14. Fringed Dressy Shorts and Matching Top
This fringed short and tank ensemble is to die for. I love how skirt-like the shorts look with the beaded tassels. A beaded clutch and stiletto strappy sandals make this outfit perfect for a night out. Buy these shorts at ASOS.
15. White Frayed Shorts and Knitted Tank Crop
A brown knit tank crop gives me major 70s vibes. I love this top paired with white frayed denim shorts. It says, “Summer in the Hamptons, anyone?” Buy the shorts at Lulus.
16. Olive Ruffled Shorts and White Camisole
A white camisole, white sandals, and a beige sunhat make these olive-ruffled shorts a summer dream. I love textured shorts. It takes something mundane and creates something new and fresh. Buy these shorts at Pink Lily.
17. Faux Leather Black Shorts With Stars and White Sweater
This is a great short outfit for cooler months. Faux black leather shorts with white stars on the back pair surprisingly well with a white sweater. Mid Calf black combat boots tie the look together. Buy these shorts at Nasty Gal.
18. Just Peachy Lounge Shorts and Matching Zip-Up Hoodie
Matching joggers and hoodies are so cute and very trendy this year. This summery take on the style includes peachy lounge shorts, a white tank, and a matching hoodie crop top. Buy these shorts at Pink Lily.
19. Distressed Denim Cut-Offs With Loop Button Cardi
The 90s cardigan craze is back. This loop button design looks fresh and hip with a pair of light wash distressed cut-offs. A metallic handbag and white sneakers complete the look. Buy these shorts at Lulus.
20. High Waisted Black Shorts With Quilted Purse and Black Heel
Black is the new black. These high-waisted black shorts look amazing with black strappy heels, a quilted purse, and a white crop top. Simple silver jewelry and black shades pull the ensemble together. Buy these shorts at Pink Lily.
21. High Waisted Nutmeg Shorts and Crocheted Top
Her look has flower child written all over it. The crocheted top is super nostalgic with high-rise nutmeg shorts and beige cowboy boots. Colorful beads and long beachy waves add to the hippie vibes. Buy these shorts at Nasty Gal.
22. Purple Running Shorts and White Sports Bra
For an athletic look, these purple running shorts add a feminine flair to her white sports bra and sneakers. The lilac hue softens the look, making it great for the gym, yoga room, or a walk on the boardwalk. Buy these shorts at Pink Lily.
23. Navy Nylon Drawstring Shorts and Harvard Sweatshirt
Graphic university sweatshirts are back, baby! I love this casual and slightly academic look. The navy drawstring shorts and white sneakers make this outfit great for lounging or an early evening outing. Buy these shorts at Nasty Gal.
24. Beige Soft Knit Shorts and Top Set With Brown Sandals
Brown and beige have a comforting aesthetic. It’s like sand on a beach. This matching short and top set is made from a soft knit design. Paired with brown sandals, they make a perfect picnic outfit. Buy these shorts at Pink Lily.
25. Mid Rise Jean Shorts with Striped Button Up and Heels
The extra-long button-up shirt looks comfy and stylish with mid rise jean shorts and heels. A black quilted purse with a chain strap makes this look nice for the day or evening. Buy these shorts at Express.
26. Pink and Green Tropical Shorts With High Neck Taupe Tank
I’ve never seen tropical shorts look so sophisticated. The pale pink and green match well with her understated high-neck taupe tank top. Braided sandals and an oversize sun hat make this beachy look pop. Buy these shorts at Pink Lily.
27. Flowy Ribbed Jersey Shorts and Band T-Shirt
Band shirts are huge right now. This Metallica graphic tee looks edgy and stylish with flowy black shorts. The ribbing on the jersey material adds texture and a hint of dressiness to the look. Buy these shorts at Nasty Gal.
28. Denim Overall Shorts With Stripe Top
I love the simple bliss of denim overall shorts. This medium wash looks super good with a red stripe top. Leaving one strap down amps up the casual Sunday vibes. Buy these shorts at Pink Lily.
29. Mid Rise Pink Shorts With Lace Bralette and Blazer
If there’s such a thing as too much pink, this isn’t it. I’m in love with this rosy look. The mid rise shorts with covered button fly are dressy and oh so chic with a lace bralette and matching blazer. A nude strappy heel would make it shine. Buy these shorts at Express.
30. Ivory Tweed High Waisted Short With Cropped Blazer
Silver buttons and nude kitten-heeled sandals make this short ensemble stand out. I like the business vibe of the cropped blazer and high-waisted tweed shorts. Ivory is light and bright but softer than stark white. Buy these shorts at Lulus.
31. Super High-Waisted Light Wash Jean Shorts With Floral Blouse
Puffy sleeves on a floral blouse add elegance and feminine flair to these denim shorts. The super high-waisted fit draws the eye to where she’s most slim. This would pair well with a beige strappy sandal. Buy these shorts at Express.
32. Long Army Green Shorts With White Crop Top
I’m digging the long shorts with a short top. Army green toughens up this ensemble, while a white crop top and sneakers keep things casual. Buy these shorts at SHEIN.
33. Denim Shorts, Beige Blazer, and Lace-Up Strappy Heels
Jean shorts are popular this year, and there are so many ways to style them. This ultra-dressy look pairs distressed denim with a beige blazer, white shirt, and nude lace-up strappy heels. Buy these shorts at Express.
34. Lavender Ribbed Shorts and Halter Set
Two-piece short sets are ruling summer ensembles this year. I adore this lavender color and the ribbed textured aesthetic. It’s super soft and feminine. Buy these shorts at Lulus.
35. Yellow Pleated Shorts and White Crop Tank
I love yellow, especially when it’s paired with the right colors and textures. These pleated shorts totally elevate her white crop tank top. Add a blazer or button-up for a business casual vibe. Buy these shorts at SHEIN.
36. Cross-Cross Back Denim Overall Shorts With Sun Hat
These adorable raw hem overalls shorts with criss-cross back look warm and summery with her sun hat. I love the colors in the hat. They work so well with the light wash of the denim. Buy these shorts at Lulus.
37. Off The Shoulder Two Piece Shorts and Ruffled Crop Top
This coral pink ensemble is dressy and light. I love the flowy textured shorts. They’re ultra-feminine when paired with the crop. Buy these shorts at Lulus.
38. 90s Baby Graphic Shorts and Tank Top With Sneakers
A little athletic, a lot casual, and very 90s. This graphic top and shorts combo looks great with black sneakers. You can’t have too much black, and this fun outfit is proof. Buy these shorts at SHEIN.
39. High-Waisted Pink Shorts and Button Up With White Tank
Soft pastels are ruling the shorts scene this year. This pale pink combination of high-waisted shorts and button-up looks airy and light. I’d wear this for a day in town or lunch with the girls. Buy these shorts at SHEIN.
40. White and Brown Gingham Crop and Shorts
Gingham always makes me think of picnics in the park. I’m living for this cute little matching combo. The ties in front give the look a playful energy. Buy these shorts at Lulus.
41. High Waisted Army Green Shorts With a White Top
Thes wide-leg shorts in army green look comfy and light. Perfect for a warm day. Sunglasses and simple jewelry are the perfect accessories. Buy these shorts at SHEIN.
Summary and Top Picks
Shorts come in a variety of colors, patterns, textures, and lengths. Mixing and matching styles to create new looks is a fun way to keep this staple fresh all year long. When in doubt, grab some accessories. Belts, shoes, and purses really make or break a look.
I’m living for all of these gorgeous short outfits, but my top three have to be:
- #5 Pleated Red Paperbag Shorts and White Tank: This outfit screams, “Be my Valentine.” I love the way the pleated shorts blend together like a skirt.
- #14 Fringed Dressy Shorts and Matching Top: A beaded clutch and strappy stiletto sandals make this fringed short and top combo a hit. I’m in love.
- #33 Denim Shorts, Pink Blazer, and Lace-Up Strappy Heels: The lace-up strappy heels and pale pink blazer turn these denim jeans into a night on the town. I love how versatile these individual pieces are.
Creating dressy looks with shorts is a fun way to spice up a wardrobe. How do you like to wear your shorts? Comment below and fill me in!