Because great shorts are a terrible thing to *waist.*
As you start to move your summer clothes out of your rotation and into storage, we have a style suggestion: Don't pack up your high-waisted shorts just yet. These shorts can work surprisingly well as transitional pieces and, when styled correctly, can be worn throughout fall and even into winter months.
That said, we're not suggesting you wear white linen shorts after Labor Day or shiver your way through your daily work commute in a pair of thigh-baring hot pants. One good rule of thumb is to consider high-waisted shorts an alternative to miniskirts when outfit planning. Another is to set aside any shorts in traditionally summery materials, but as with all things, there are exceptions to these style rules.
High-Waisted Shorts Styles
While there are loads of different high-waisted shorts styles, only a handful are transitional weather standouts. Pleated high-waisted shorts are a great choice for fall as they often appear in more heavyweight fabrics like wool and leather, in addition to cotton and linen. Denim is another top-notch autumnal textile and our reigning fave casual high-waisted shorts style. Last, but not least, paperbag high-waisted shorts are a great in-between-seasons secret weapon.
Because of their baggy fit, you can tuck in thicker tops like sweatshirts and cable knit sweaters without disrupting the lines of your look. If you plan to wear high-waisted shorts throughout the fall, we highly recommend taking advantage of summer clearance sales and getting yourself a pair of paperbag shorts so you can tuck in even the chunkiest of sweaters without feeling cinched or squeezed.
How to Style High-Waisted Shorts
Wearing high-waisted shorts in cool or chilly temps is all about layering, but that doesn't mean you have to abandon your summer go-to styling techniques. Crop tops and bralettes are still fair game, but we recommend adding a blazer or cardigan layer, plus a jacket on top. Long-sleeved tops are a foolproof option, but short-sleeved tops can work, especially when worn under a tucked-in sweater.
To give the illusion of fewer layers, try a long-sleeve thermal (fully tucked in) paired with a half-tucked button-down shirt. Worried about all these layers looking bulky around your waist? Don't fret. Just add a statement belt to redirect the eye and you'll be good to go.
With these styling types and shorts styles in mind, you'll have no trouble making these 21 high-waisted shorts ideas work for you all season long.
Try '90s Styling
We can't believe it either, but knee-length jorts — a.k.a. Bermuda jean shorts — have emerged as a celeb-loved trend. Since these high-waisted shorts already have something of a retro vibe, we suggest taking that trend and running with it by adding a graphic '90s crewneck sweatshirt.
Pair Cozy with Sheer
As we mentioned, wool high-waisted shorts are a perfect piece. Not only will they keep you snug, but they happen to look gorgeous with a matching trench or peacoat.
Monochromatic dressing is always in season, and wearing a high-waisted shorts suit or matching set is a great way to take the trend for a test drive. Not only do shorts feel a bit more playful than trousers, but they're easier to dress down for a casual outing with a pair of slides or sneakers.
Add a Rugby Top
For a casual and high-waisted shorts look, try pairing an oversized rugby top with snuggly cotton bottoms. A pair of knee-high boots gives a rugged effect while heels deliver a cheeky but luxurious high-low aesthetic.
Create Cohesion with Details
If you're unsure of how to pair a fall top with summer bottoms, we recommend looking for pieces that share design details as a starting point. Case in point: these ruffle waistband high-waisted shorts paired with a ruffled blouse.
You can also try building a high-waisted shorts outfit with a focus on contrast. Much like mixing prints, mixing textures can create a bit of high-fashion chaos (in a good way). If you have high-waisted shorts in a thicker fabric, try adding a silky, lightweight blouse and a pair of heeled mules or boots in the same color family.
Channel Vintage Varsity Vibes
Embrace the homecoming spirit with a varsity jacket and high-waisted shorts. This look can be warmed up with a preppy pullover or kept cool with an equally preppy, but less weighty, polo shirt. If you're really vibing with back-to-school spirit, add a pair of schoolcore loafers and a ribbon to your hair.
Slip on Some Sequins
Dress up a pair of high-waisted shorts for a night out with a fully-sequined blouse. The disco energy can be enhanced with similarly sparkly accessories or toned down with muted, all-black pieces.
Play with Proportion
If you have a matching bralette or crop top and high-waisted shorts combo you love for summer, you can still make it work for cooler months. Adding an oversized, slouchy cardigan and a pair of roomy rainboots creates a cool juxtaposition.
Grab a Cozy Duster
To create a look with gorgeous long lines, you can't go wrong with shorts, a duster sweater or jacket, and thigh-high boots. Not only does this look deliver a sizable amount of quiet luxury, but there are plenty of opportunities to add layers that'll keep you extra cozy.
Feature Graphic Accessories
Denim high-waisted shorts are something of a casual blank canvas you can use to try out more experimental styles. Statement bags, vibrant boots, and neon color palettes are all slightly toned down when worn with jean shorts.
We've said it once and we'll say it again: We love a shorts suit. High-waisted culotte shorts keep this look conservative enough for a day in the office, but the relatively high hemline means you can spice things up with a pair of knee-high or over-the-knee boots.
Layer Slouchy Sweaters
Can't decide between your two favorite cardigans? There's no reason not to wear both. This high-waisted shorts outfit works best with one cardigan tucked in and the other worn loose. Because the stacked aesthetic is the main element of this look, feel free to mix prints. A single shared color in both tops will keep things cohesive.
Do a Half-Tuck
We couldn't help but wonder: What's the point of high-waisted shorts if nobody can see the waistband? For a look that's effortlessly cool, try tucking just half of a button-down shirt into high-waisted shorts and adding a statement belt to accentuate your waist.
Get Playful with Stripes
While stripes can sometimes become visually overwhelming in a full suit, even dramatic stripes worn on a blazer and matching shorts are less dizzying. Less of one pattern leaves you open to add even more stripes. To keep things from feeling too busy, we recommend pairing a matching set with pieces featuring stripes in different widths and colors.
We love leaning into menswear with an oversized blazer and button-down shirt worn open, especially with high-waisted shorts. Elevate the look with luxe accessories and continue the layering theme with chain necklaces and stacked bracelets or rings.
Play Up a Bold Print
If you didn't get a chance to wear floral or printed high-waisted shorts in the summer, you've still got time to show them off. Rather than wearing a matching sweater or shoes, make your statement shorts stand out even more by choosing complementary colors in the rest of your 'fit.
Try Statement Metallics
Much like a statement sequin skirt, metallic high-waisted shorts are bottoms that will feel fashion-forward, even when worn with basics. A pair of knee-high boots keeps this 'fit firmly rooted in the realm of fall fashion.
Amp Up Athletic Shorts
Who says track shorts can't feel high-fashion? Elevate a pair you'd otherwise wear to the gym with luxurious accessories in the same color family. Adding a blazer only adds to the high-end feel of this look.
Switch Up Your Shoes
Shorts worn in the fall already subvert seasonal expectations, so it makes sense to keep that idea going strong with your footwear. Adding chunky high-heel sandals and thick socks is an elevated approach, but you can create the same aesthetic more casually with Birkenstocks or slides.
Add Sheer Stockings
If you'd rather not deal with outerwear layers but want your high-waisted shorts to feel more fall than summer, a pair of sheer tights can drive the seasonal point home. Combat boots are another oh-so-fall element you can bring into play.
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