27 Chic Outfits to Wear with Shorts with Styling Tips

There is no doubt about it that shorts are one of the most comfortable and versatile clothing items out there. They are especially great to wear in the hot summer months. However, with the right styling and added layers, they can definitely be worn during the fall and spring as well. Regardless of your body size or shape, it is possible to find a pair of shorts that works for you. And hey, not only are they versatile clothing pieces but they provide the perfect means to show off those beautiful legs of yours!

Best Shorts Outfit Ideas

Styling Tips

  • Always buy shorts that flatter your unique figure. Don’t opt for Daisy Dukes if they don’t flatter your particular assets. There are all kinds of stylish options which women of all shapes and sizes can choose from.
  • Longer shorts create the impression of shorter legs, while short shorts lengthen the leg, giving the impression of height.
  • Shorts that flare out toward the bottom, rather than hugging the thigh, are flattering for bulky girls and curvy women alike.
  • Floral or tropical print shorts can be a fun and flashy addition to your wardrobe, especially in the summer months.
  • Increasingly stylish, fashionable, and flattering, high-waisted shorts are making a big comeback. Adding one or two pairs of high-waisted shorts to your wardrobe can result in several gorgeous outfits.
  • Avoid plaid or similarly printed shorts if you are very curvy; stick to streamlined shapes and dark or neutral colors.

↓ 27- Leather Shorts

These studded leather high-waisted shorts are an eye-catching, trend-setting piece that is sure to show off your gorgeous gams! Pair with a simple white tee (tucked in) and a pair of knee-high black slouching boots. A simple necklace, a couple of rings, and a single bracelet are all you need to accessorize. Here are some more Cute Leather shorts outfits.


↓ 26 – Super High-Waisted Shorts

This amazing outfit (worn by the beautiful Selena Gomez) perfectly blends style with professionalism and elegance. Sleek hair, open hoop earrings, and nude heels are the perfect accents to this look. This little matching set of shorts and crop top can be worn to a party or other dressy affair. The added blazer (fitted with cropped sleeves) provides the perfect balance to keep this look from being too revealing.


↓ 25 – Holiday Outfit

As the warm season draws to a close, this outfit could not come at a more perfect time. Maybe you are headed out for a holiday before school starts; maybe you are all set to hit the beach! Whatever the occasion, this outfit is versatile enough that with just a few tweaks, you can make it suit your every need!

Simply pair a blue tank with your favorite pair of white shorts. Accessorize with a matching belt and purse, and add in some cute elements like a cute and feminine scarf and sunglasses. Pop on a pair of sandals and you are good to go!


24 – Autumn Outfit

Here is a great example of an early autumn outfit that perfectly captures the essence of the coming season!

What we love about this look is that it’s both feminine and practical. You can wear this to go shopping, to grab lunch with friends, or as a weekend walking ensemble. Simply match your shoes with your shorts and layer a maroon colored sweater over a white collared blouse. Accessorize with sunglasses and a red lip.

↓ 23 – Paperbag Shorts with Top

A trendy version of shorts these days is the super cute paper bag shorts.

You can grab yourself a pair of these pretty much anywhere, whether online or otherwise. They ruche around the waist with a belt and they are a modest length. They are great for beach parties, boating, shopping, or simply grabbing a coffee.

For this look, these neutral blended shorts are paired with a cute white camisole and beige sandals. Accessorize with a round straw bag and a necklace.

↓ 22 –  Summer Street Style

This a cute outfit that women of all ages could easily pull off!

Pair a loose, dark-colored tee with some white shorts. Sleek hair and black combat boots provide a fun contrast to this look. Accessorize with the purse of your choice!


↓ 21 – Printed Shorts with Denim Shirts

For a casual day or a beach party, printed shorts work really well with a denim or chambray. They are crazy, funky, and fashionable indeed. Since denim is a relatively simple material, you can usually get away with wearing a full print on your shorts, but make sure to streamline your look with the louder prints if your denim is too simple.


↓ 20 – Funky Festive Outfit

This ultra-stylish and trendsetting look features a pair of green leather shorts paired with a glittery sequined top! Give it a try today for your next birthday bash or holiday celebration! It’s chic and eye-catching and when paired with some beige or calf-colored sandals, it becomes quite elegant, too! Accessorize with a tote bag and celebrity-style sunglasses. For more ideas, do have a look at these Sequins Outfits.


↓ 19 – Party Girl Look

A blazer with matching shorts can be a super high-end look for the daring girl who likes to push her fashion to the edge!

You can go with or without a shirt underneath (we recommend a bandeau or crop top!) and opt for a sleek hairstyle to pull your look together.

Add some extra inches to your height by choosing from peep toes, pumps or platforms. Make sure you go for one solid matching color for your suit as well. SO21

18 – Celebrity-Inspired 

When in doubt over any given wardrobe piece, look no further than our modern celebs!

Celebrity fashion might seem a little out of reach for us normal gals. But what is great about these looks is that they can be easily adapted to suit almost any body shape or lifestyle out there!

Take a look at these four outfits below and then go have a wander through your closet. Chances are, you have at least something similar to one of these ensembles that you can pull from. Whether it’s a funky printed tee or a patterned blazer, high-waisted shorts or a pair of black pumps, there’s something here for everybody! Get creative and do some experimenting. Dressing up a good pair of shorts has never been so simple. SO20

↓ 17 – Date Night Outfit

Keep your date night outfit budget-friendly. An ethereal chiffon blouse laced with a collar looks impressive with gold metallic textured shorts. Keep your accessories to a minimum and opt for a sleek brushed-over hairdo. Pop on a pair of strappy heels and you are ready to hit the town with your honey!


↓ 16 – With Boyfriend Blazer

This is an easy and comfortable outfit that looks more complex than it really is! Score.

All you need is to pop on your favorite graphic tee with a pair of lighter-colored metallic shorts. A boyfriend blazer and glam black heels add a layer of sophistication to this look. Accessorize with a chic watch and oversized black sunglasses. This is a great look for a casual lunch or a trip to the theater.


↓ 15 – Denim and Sequin Shorts

Why not get patriotic and try out this look?

For the all-American gal who loves to show off her love for her country, give this flag-styled top a try. Pair with sequined denim shorts for added glitz and pile on the necklaces and bracelets to keep the look fun and youthful! This is a great outfit for Independence day, an outdoor barbecue or a music festival! Here are some super Cute Outfits Ideas to Wear with Denim Studded Shorts.


↓ 14 – Shorts with Knee High Boots

This is a great look for the girl who likes to look a little goth while also remaining feminine. All black is sleek and stylish and for a lot of us, our preferred color palette of choice! For this look, pair some lace-trimmed shorts with knee-high boots and a top. Feel free to go a little bold with your jacket. This edgy piece is eye-catching and super fashionable. Accessorize with a small purse and a statement ring for your hand.


↓ 13 – Fashion Blogger Style

Who among us doesn’t want to live the fashion blogger life every now and then?!

Well, this look will let you do just that. This is a gorgeous ensemble that really lets you show off your sense of style as well as your gams! Pair some white FAV shorts with a sea-green blouse and some statement heels. Retro shades and an eye-catching necklace ties the look together and makes you summer-party ready!



↓ 12 – Plus Size Shorts for Curvy Girl

Size does not matter when you are comfortable with your body.  Casual shorts with a blazer and tee is a cute and stylish look on curvy girls. Also, check out our earlier post on How to Wear Shorts for Plus Size.


↓ 11 – Hipster Look

Here is a great example of how to wear shorts in winter or autumn. Simply layer them with leggings or tights and boots. A white tee with a jacket and short cape-style coat is perfect the hipster college girl!


↓ 10 – Summer Beach Party

It’s all about the colors with this look. Go bold with some peach-colored shorts, paired with a turquoise or sea-green top. Matching shoes and sunglasses give this ensemble a preppy vibe, but it’s instantly made classy with a gorgeous statement bag. Add some gold earrings to accessorize!

↓ 9 – Chic Street Style

One of our favourite looks hands-down is this chic, edgy street-style outfit!

An off-the-shoulder black blouse is tucked into a pair of short denim shorts and paired with some super strappy heels! Accessorize with round sunglasses and a black bag.


↓ 8 – Celeb Summer Style

Here is a great example of how to wear some basic denim shorts!

Pair with a fun top or a tee with a cardigan. Bohemian styled sandals and a cute backpack purse pull the look together. Don’t forget your sunglasses!


Do have a look at 32 beautiful denim dresses to inspire your daily fashion

↓ 7 – Spring Outfit with Leather Shorts

This is how you wear leather shorts in the summer! Keep the rest of your look bright with light, breathable fabrics and opt for colors that are summery and fresh. A casual top with a cardigan and ballet slipper shoes really pulls this ensemble together. Great for spring, too!


Also, check out Leather skirt outfit ideas 

↓ 6 – Distressed Shorts for Every Figure

Basic doesn’t always mean boring. This simple but gorgeous look is one you could easily wear today! A boyfriend top is tucked into some cut-offs with a thin black belt. Accessorize with some gold bracelets, and have fun with your footwear. Headed to a party? Pop on some combat boots or Doc Martens. Going for a casual dinner with friends? A sandal or small heel will dress up this look.


5 – Linens

These split detail linen shorts are comfortable and affordable for all. Pair them with a light-colored blouse and statement sandals. Accessorize with cat-eye sunglasses and a cute over-the-shoulder bag.


↓ 4 – Sheer Outfit

Rendered in rich brocade or gleaming satin, these luxe-looking shorts are ready for a night on the town paired with a silky camisole and strappy high heels. Just remember the shinier the better! Here’s the ultimate guide on How to Wear Sheer Outfits.

↓ 3 – Embroidered Outfit

Inject a shot of color and embellishment into your summer wardrobe with a pair of embroidered shorts. These punchy designs beg for a music festival outing when paired with a diaphanous top and studded sandals.

↓ 2 – Party Look with High-Waisted Shorts

Here is a celeb who knows how to rock a good pair of high-waisted shorts. Like Miley, basic black high-waisted shorts with a white blouse looks glamourous if paired with a sequined blazer. SO27

↓ 1 – Runway

When in doubt, wear black. There’s nothing more versatile, sophisticated, sexy, and conservative—all at the same time.


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