10 Chic Ways to Wear Short Shorts: A Guide for Women
Updated: Mar 25
Short shorts tend to get a bad rep. They’re generally considered a rather trashy piece of clothing due to their skimpy nature that can leave little to the imagination. I can recall the first time I wore a pair of shorter shorts when I was an early teen. My mom would not have it and did not allow me to leave the house with them on.
It was not until my early 20’s when I was living on my own, that I mustered up the college to wear my first pair of ‘hot pants.’ Before then, the shortest shorts I would wear would be Bermuda shorts or athletic shorts such as basketball shorts. Society had wired me to believe that a pair of short shorts were considered trashy.
Nowadays, you can find women across social media sporting all types of short and long shorts and contradictory to societal norm, they would not be considered trashy. When it comes to shorts shorts, it’s all about styling them as well as respecting dress codes. There is a time and place for them and that is typically a casual summer event.
There is also a classy way to style them it that is your preference or you could create sexy outfits. The choice is yours.
This blog post is not going to be shaming or policing people about whether or not they should wear a pair of daisy dukes. It would rather show you different ways to style a pair of shorts. I would be sharing both less conservative and more conservative ways to create a chic shorts outfit.
Either way, your legs are going to be on display and so you want them to look their best. You’ll also see how you can easily create both casual looks as well as dressier outfits with a pair of shorts.
Before we hop into the various outfits and looks you can create with shorts, I would like to share some sites where you can shop for great options of shorts. If you are looking to add some to your shorts collection, you should definitely check them out. If these are your first pair of shorts, you’re in good hands.
*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.
Where to buy good short shorts?
i) Old Navy
If you’re going to wear shorts often during the warmer months, you would most likely be opting for denim shorts. They’re probably the most popular type of shorts out there and maybe the easiest to style as well. Jean shorts can be paired with casual tops for a laid-back look you can rock when it’s hot outside. These cut-off jeans shorts could be paired with a simple top for some everyday wear perfect for the warmer weather.
I love wearing shorts at home. It’s easy to just throw on an old t-shirt on top to get some cleaning done or to chill and watch TV. Jean shorts could feel a little restrictive at times and so yoga shorts tend to be my go-to. They could be worn to complete a home workout or laze about all day. THESE ones from Amazon are a great choice as their elastic waistbands allow for more free movement.
You get a nice range of dressier as well as more casual shorts on Nordstrom. You can show off your long legs at semi casual events by pairing your shorts with a professional piece such as a structured blazer.
This would elevate your look and balance out the exposed leg look you’re serving. THESE tropical linen blend shorts would be a good choice for a dressier event during the warm months.
If you like to do a lot of exploring during the summer but wish to be able to enter certain establishments with a casual dress code, cargo shorts are an option to explore. They’re easy to pair with casual tops like tank tops or with button-down shirts for a more formal look. THESE ones from Shein are on the shorter end but could be easily paired with different tops.
If you are looking for shorts to wear for date night or to a birthday party, you need to check out Revolve. You can show off your best features (your legs) in a pair of flirty short shorts featuring a lace detail.
Shorts with a wider leg opening like THESE ONES are especially flattering on women with thick thighs like myself. They take some attention away from the thickness of the thighs and focus on lengthening the legs.
vi) Pretty Little Thing
PLT is my go-to website to shop for bike shorts in particular. I love how light and comfortable they are and they’re easy to with crop tops or oversized shirts. They also come in so many colors that you’re bound to find a pair that goes with your personal style. THESE white shorts would work great with a hoodie or you could slip them underneath your summer outfits to avoid chub rub.
Now that you have a good idea of where to shop for short shorts, we can dive into the different ways to style them. I would be sharing outfits you can put together with both short and longer shorts. This way, if you’re not comfortable wearing the shortest of shorts, you can still pull off some shorts outfits perfect for the warm weather.
The 10 best short shorts outfits
1) With a tank top
This is one of the most popular ways to style a pair of shorts. Create a simple casual look that you can wear all summer long by pairing your shorts with a simple tank top. A white tank top paired with white sneakers is my favorite way to style a pair of denim cutoffs. Complete your look with a pair of sunglasses and a crossbody bag.
You can add a denim jacket to your casual look if you’re dressing up for a chilly summer night. This is a look you could wear to the mall, to grab some ice cream or to chill at the coffee shop. Remember to load up on the sunscreen!
THESE Levi cutoff shorts would be the perfect choice.
2) With an off-shoulder top
An easy way to create a cute and flirty look with a pair of short shorts is by pairing them with an off the shoulder blouse. A long-sleeved blouse is a great option to go with if you want to show less skin or if you’re insecure about your arms. Choose an off the shoulder top in a neutral color for an easy summer look.
Get the look HERE
For footwear, you could opt for a pair of flat sandals or flip flops for a very casual look. If you’re feeling a little daring, opt for a pair of cowboy boots and create your own Jessica Simpson moment. Don’t forget the cowboy hat while you’re at it!
3) With a button-down shirt
The best way to create a semi-professional look with a pair of shorts is by pairing it with a long-sleeved button down. A pair of chino shorts would be a great choice to create a stylish out-of-office look during the summer. You could wear this for a work barbecue or drinks after hours with co-workers when it’s hot outside. Try to go for longer shorts if you’re dressing for a slightly more formal occasion.
Image souce here
If it’s a particularly hot today, choose a pair of linen shorts instead. Linen absorb sweat, leaving you nice and dry on a hot day because who wants sweat stains in their groin area? Even in casual situations, we want to put out best foot forward.
4) With a sweater
If it’s not exactly a warm sunny day but you are bent on rocking a pair of short shorts, you could pair your short shorts with a sweater to create a chic yet casual look. Choosing a sweater means you get to play around with your footwear. You could opt for a pair of boots, heels or white sneakers to complete your look.
Get the look HERE
A chunky knit and shorts works to run some errands around the neighborhood or a quick trip to the mall. You could also add a pair of tights under your shorts to make your look more interesting. Add a pair of combat boots to complete this casual look.
5) With a crop top
A crowd-favorite on the hottest of summer days is this classic pairing. Crop tops have come a long way and they can now be flattering on all body types. If you do not wish to show your belly in your crop top, choose a pair of high-waisted shorts and perhaps a slightly longer crop top.
Get the look HERE
Feel free to play with crop tops in bright colors, especially if your shorts are in a solid color. You could also add a kimono on top to make your shorts look more fashionable. Throw on a pair of sneakers and you’ve got yourself a stylish summer festival outfit. Check out my post: How to wear a kimono with jeans and other items for more kimono outfits inspo.
6) With a hoodie or sweatshirt
Looking for a cute outfit you can put together within seconds to walk the dog? Pair any of your old oversized hoodies with a pair of short shorts and head out the door. You’ll be able to stay slightly warm, especially if you’re someone who tends to feel colder on your upper body.
Get the look HERE
This is also a good look you could wear to a university lecture on the weekend and you have nothing to wear. Feel free to add a pair of black leggings or tights for an extra layer of warmth. Sneakers or boots are the best choices of footwear to go with to complete your look.
7) With a bomber jacket
Make your shorts outfit more high-end and trendy by pairing it with a bomber jacket. A comber jacket is a cropped jacket that is typically on the puffy side. The cropped style would give the illusion of a small waist while also keeping you warm. This look works best with more casual shorts such as biker shorts or denim shorts.
Get the look HERE
A cropped top or simple tank top could be worn underneath your jacket. Sneakers are most commonly worn as footwear and you can complete your look with a fanny pack and oversized shades. Face caps and bucket hats are other accessories you could use to really make your look stand out.
8) With a blazer
If you want to stand out at your next brunch or pool party, try pairing any top of your choice with your short shorts and then adding a blazer on top. Oversized blazers are my favorite type of blazer to create this look with. This is such a chic look you could wear to the airport, for drinks and even for a night out.
Get the look HERE
If opting for a pair of bike shorts, try going with a tank top or crop top. On colder days, you could even wear a cropped sweater with this look. If you own a pair of Nike’s now is the time to throw them on.
9) With a leather jacket
We all know leather jackets are a wardrobe staple and so it makes sense that they should be able to be styled with a pair of short shorts. You can recycle your shorts from last year and create different outfits just by changing your choice of outerwear. A brown or black leather jacket works best during the fall.
You should play around with different colors of jackets during the summer days. For footwear, opt for a pair of combat boots to create an edgy look. You could also wear a pair of more formal ankle boots such as Chelsea boots to create a sleeker look. You could wear a simple graphic tee underneath your jacket to make your look more streetwear.
10) With an oversized t-shirt
This is probably my personal favorite look on this list. I revert to a big old tee and shorts when I feel bloated. It’s really easy to make this look trendier by throwing on a pair of cool sneakers and a cap. Rock this look to head to the grocery store, the mall or just to relax at home. It’s also a look you can pair with a fanny pack and look trendy in.
Get the look HERE
A pair of black shorts are a good choice to go with. The would be so easy to pair with any other colors of tops. Throw on an oversized blazer or jacket to elevate your look with minimal effort. I also love how you could swap your sneakers for a pair of high heels and it would transform your look completely.
Over the years, we have seen how short shorts have been oversexualized. While it is true that they tend to be a more risqué piece of clothing, it does not mean you can’t wear them on a regular day. It’s all about choosing the right shorts for the right occasion. Start with shorts that compliment your skin tone.
Short shorts could be worn to a pool party or a trip to the mall, but I would not recommend wearing a pair to go visit a museum or embassy. I hope that you have gotten sufficient inspiration that you can refer to for a long time once shorts season is upon us. Try playing around with different styles of shirts or tops to see what works best for you.
Do check out my post: The top 7 tops to wear with a skater skirt if you are looking for ways to style a mini skirt during the warmer months.
I also have a post titled The 5 best ways to wear high waisted skirts which serves as a great guide to pairing the right tops with different styles of high-waisted skirts.
If lace shorts are your shorts of choice, check out my post: 6 Outfits to Wear With Lace Shorts.
Headed to Disneyland? Check out this post: The Ultimate Guide on WHat to Wear to Disneyland.
If you're a part of the thick thigh community, check out my post: 12 Tips on How to Wear Shorts With Big Thighs.
Until the next post,