I feel like the world of fashion has been announcing Y2K influence “is back!” for multiple seasons now, but somehow, for some reason, this time it actually… feels real.
Maybe it’s just the circle of influence I follow on social media, but lately I can’t seem to escape every item that was in my 2006 teenage closet:
Long shorts.
Gauchos.
Capris.
Noticing a pattern here?
The layering of tanks, bandanas used for headwear AND tops, chunky platform sandals, the list goes on.
But those longer shorts, that’s what my mind is really focused on. Because for the last handful of years I buy them – bermudas, jorts, whatever you want to call them – and every year they collect more dust than I’d like to admit.
THIS is the year I want to really figure out how to wear them…but, you know – as an adult, not a junior in high school.
What I Bought: Gap Midrise Loose Bermuda Shorts
Gap’s Midrise Loose Bermuda Shorts are a cautious 8” – not short by any means, but certainly not the longest or baggiest style that we’re going to be seeing this summer. They felt like an easy starting point before diving off into the world of rolled waist gauchos (gulp).
shorts (29)
These are a super soft, lightweight bermuda short. We’re talking paper thin – but in a good, surviving-southern-heat-waves kind of way.
I sized up one, from my regular 28 to a size 29, and they fit very comfortably, however next time I’d probably even go for a size 30 as I really love a loose fit denim in hotter weather.
If you haven’t sized up in denim shorts yet: you have to. It will lowkey change your life.
5 Easy Ways To Wear Bermuda Shorts
In my emotional whirlwind of putting outfits together each morning, when I’m haphazardly throwing on bermuda shorts something can often feel off. It’s as if I don’t understand longer shorts very well, or how they fit within my wardrobe.
shorts (29) | tank (L) | sweater (L) | shoes
Since I found this new pair of longer shorts I’m excited to wear, I thought I should really pause and do some homework.
Find a few solid styling options that work within my closet.
Less formulas, if you will, and more like my personal notes on what parts of my closet I can pull from + play with when wanting to wear longer shorts.
1. Minimal footwear is the winner
I’ve never subscribed to the belief that when wearing something baggy in my outfit I need to balance it out with something fitted, but I DO find myself gravitating towards more minimal footwear when wearing baggier clothing.
shorts (29) | tank (L) | sweater (L) | shoes
Think: flip flops, strappy sandals, thin heels, a ballet flat, etc.
Even at 5’10” I find myself wanting to elongate my legs when wearing longer shorts, and a minimal shoe helps create the illusion that your leg keeps going, whereas a chunkier sock or shoe can chop up your height (see: “what I’m skipping” at the bottom of this article).
shorts (29) | top (L) | similar flats
2. Little tops work
shorts (29) | tee (L) | sandals
Fitted tank tops and cropped linen tees look great with a relaxed bermuda short. It’s that effortless summer outfit I’m always hoping to create when the weather gets hot and sticky.
shorts (29) | tee (L) | sandals
3. But big tops work, too
shorts (29) | top (XL) | similar flats
There’s no need to stick to exclusively to small tops, however. Looser, longer tops match the long nature of jorts perfectly.
Sweaters are easy for spring days and cooler summer mornings. Oversized button downs paired with flats would be a great choice for brunch, and oversized hoodies are an easy go-to for busy days and lounging.
shorts (29) | hoodie (XL) | shoes
4. A crewneck + flip flops is the easiest
shorts (29) | sweatshirt (XL) | similar sandals
What feels the most like ME is a relaxed crewneck sweatshirt and flip flops. This is truly the easiest, throw-on-and-go outfit I know I wouldn’t even have to look twice in the mirror for.
5. A sweater + ballet flats are the perfect chic balance
shorts (29) | similar sweater | similar flats
For something a little sweeter, ballet flats and a sweater feels spot on.
You can find the same “sweet spot” balance with a minimal loafer + polo top, too.
shorts (29) | sweater (XL) | similar loafer
Achieving this look in hotter temperatures is do-able, too, thanks to open-weave linen sweater options (my fave right now are at Banana Republic).
What I’m Skipping: Chunky footwear and/or a big sock.
shorts (29) | hoodie (XL) | sneakers
I didn’t hate this socks + dad sneaker NEARLY as much as I thought I would, but it probably won’t be my first or even second go-to for an easy outfit grab in the AM (unless I’m headed straight to a Disney park). A quick fix: opt for a minimal sneaker.
And although I love how the masculine leaning loafer + socks looks paired with baggy shorts when I see it on Pinterest, it takes work when doing this in real life. A quick fix: find a loafer you can skip the sock while wearing.
The Verdict: Don’t Overthink Long Shorts
I was pleasantly surprised with how much I liked paired with these bermuda shorts, even with my ghostly white winter legs.
I’m not sure if it’s because I’m wearing a relaxed midrise style, or if because I sized up so they were extra comfy, or if my mind has simply, finally come back around to a longer short, but styling these this year didn’t feel nearly as hard as they have felt in the past!
Xx
Amy
Wanna keep hanging? Let’s be friends on Instagram or come find me on TikTok !!
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I love Bermuda shorts because they hide my saggy upper legs. They also bring me back to the 80’s.