Inside: 11 perfect grey short outfits for summer style 

Some of the best fashion trends have all been very street heavy and street focused. And the best thing about that isn’t just how cool it looks and how much we can value it, but it’s also how comfortable all of the styles are!

Slouchy jeans? Yes. A chunky sweater with a skirt? Absolutely yes. Sweats being made trendy and classy? Yes PLEASE!

So as we move into summer and keep rocking with the summer temps wherever you are, as we start to look into different cool and trendy outfits, just remember that sweats are trendy! Sweatpants and sweat shorts are cool and totally fair game when it comes to dressing and styling outfits in a more street style.

Now, this goes for any color of course, but realistically the most classic sweats color is grey. We all love a good pair of slouchy grey sweats in the most basic branding, but what if we made it a little more fashionable? There are so many options for this and ways to make it happen. So if you’re on the sweats train and really want to go with the grey shorts that are everywhere these days, here are the best grey ideas to combat those bright colorful short outfits & spice up your street style this summer.

Four women in outfits with grey shorts

What To Wear With Grey Shorts

Grey shorts are so easy to style, it’s simply a combination of greyscale neutrals that make up the perfect outfit. You can totally pair colors with grey, but it’s definitely more of a cool neutral so you’ll want to keep to a few specific colors and shades.

Since it is a cool tone, when you put color with grey, light blues tend to go the best with it, but you can use any bold and basic color like a deep purple, a bright red, or a pastel yellow to make a statement. These colors can be accented by the grey really well, creating a nice balance of neutral and color. It can be really refreshing to the eye to use a neutral that isn’t straight black! So this is a perfect option for mixing with some colors.

You can also totally go full grey sweat set, which is a classic sweats look. How many of us remember the staple baggy grey sweats that we or our parents had in the 90’s and 2000’s that were just always pulled out on snow days? And they of course always had the matching zip up hoodie to go with! Light grey is just always a staple sweats color, so there’s no better color to get the matching sweats set in.

My personal go to for these looks is so simple. While I love color and while I love a good matching set, my favorite top to wear with a pair of grey shorts is a plain white baby tee. It’s too perfect, too flattering, and too classic. It gives the perfect off duty model look, and it’s super easy to dress up or dress down. But either way, you’re looking pretty chic.

Whether you’re rocking grey biker shorts, sweat shorts, or anything else, there’s a ton of ways to wear these staple pieces and look stylish while doing so.

Let’s look at two different ways to really style some grey shorts. Cool street or dressed up.

Tips To Look Cool In Sweats

If your whole goal is look like the cool street style version of yourself while rocking these grey shorts, I’ve got some styling tips for you. While dressing them up and dressing them street might be two very similar processes, there are some details that you can definitely make changes to that will change the entire style of your look.

Street is all about urban styles and trends, as well as what’s trending with younger generations. While it’s a lot of recycled trends from the 90’s and 2000’s, the peak of street style, this is what’s trending here and now on the streets of 2023.

The big sneaker trend of the last few years came from the uprising of the street style. In major urban cities, everyone wears sneakers with their work clothes because they are likely to walk to commute to and from work. And this is what made sneakers acceptable with nicer clothes. We are so thankful for this trend… At least I am!

So throwing on your favorite pair of sneakers, whether they’re a basic white leather staple sneaker or a trending limited edition of New Balances or Nike, sneakers are the first step. Another current big trend in street style is the baby tees. You can get a plain basic one or even a vintage logo one. Either way, a baby crop is perfect with these shorts.

A baggy vintage tee shirt always wins the crowd, or even an oversized white or black button down is a cool idea to make this a little interesting with a contrast of style and formality. Contrast is always a really cool element to play with especially with casual street style and making it a little cooler.

Adding a cool jacket like an oversized denim or a vintage racing jacket is one of the coolest ways to add something new and fresh to this look.

Throw on your over the ear headphones and the coolest pair of sunglasses you own and you’re good to hit those streets and look oh so cool while simply rocking your sweats.

Tips To Dress Up Sweats

Dressing up in sweats has definitely become a really fantastic phenomenon in the latest few years. Of course we’ve loved the resurgence of the Juice tracksuit, but when you’re in a classic pair of sweats, how do you feel a little more dressed up than normal?

I would start with turning this into a matching set. This isn’t absolutely necessary, but a monochrome moment, even in sweatpants, is just an elevated moment for this outfit. Even with a sweatshirt, you can layer a leather jacket over it, and pull the hoodie out if you have one, and it’s an elevated jacket moment.

Throwing on some cool loafers with some white scrunched crew socks makes this a little preppy and trendy.

Don’t forget a good pair of chunky hoop earrings, and a corresponding necklace or even a necklace stack.

Using a trendy hair style like a slicked back bun or mini braids at the face framing can help elevate this into something more than just an errands outfit.

Two girls wearing sweat shorts and cute outfits

Grey Short Outfits

1. Vintage Logo
2. Baggy
3. Baby Tee
4. Biker Shorts

A girl in grey shorts, white button down, and a belt bag

Cute Grey Short Outfits

5. Matching Set
6. Urban
7. Draped Sweatshirts

Three cool girl styles with athletic shorts

Style Ideas

8. Graphic Tee
9. Leather And Swim
10. Earthy
11. White Bodysuit

Street is my favorite style, even though I totally identify my style as more of a girly and fun style. It’s so nice to be able to put some attention on a more cool and casual style and it not only be acceptable but trendy.

Wearing sweats as normal street clothes has to be my personal favorite trend and definitely makes me feel like I have my life together when I have a matching set on and it’s all styled and dressed up.

However you prefer to wear your grey shorts, maybe it’s even just for a cute movie night or your day off running errands, but either way it’s going to be a cute outfit that you can break out for anything you have ahead of you.

Personal style can still shine in your sweats, even if you have the cleanest and preppiest style, it’s still a move to throw on some sweat shorts and style it like you’re not even in comfy clothes. That’s a flex.

If you want some more comfy outfit inspiration, try these 47 comfy outfit ideas to wear anywhere.

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