My Favorite Way to Wear Shorts — With Something Long


The saying in Portland is that summer doesn’t actually arrive until after July 4th. Well, it’s the 5th as I’m writing this and it is sweltering hot…so, Hi Summer! And with its arrival comes “what the heck is this jeans girl going to wear now?” I honestly have the hardest time with summer outfits…save one. I shall now share with you my favorite outfit (many years tested now) when summer temps do heat up.

I love my cutoffs (#denimrelationship), but sometimes when I wear them with a tank or tee I just feel…hmm…I don’t know. Too casual mostly, too young maybe (maybe not though), or like I can only get away with them when I’m headed to the lake or the pool. Ya know? Depending on the plans for the day, sometimes I just feel too bare.

You may have seen in years past my fix for this…wearing a side split dress or high-low dress half-tucked into shorts. I lurve it. Have no fear because I’ve found an updated top that still works with this scenario. But first, let’s take a look back…

First Version of My Favorite Way To Wear Shorts

Whew. First of all, look away from that hair color. Ha. What was I thinking? This DIY maxi dress into side split tee was my favorite, favorite way to wear my cutoffs, feel more covered but still cool, and feel a little more… shall I say dressed up? Dressed-up for summertime anyway. This was great, but it’s still a lot of fabric y’all. So…

Second Version of My Favorite Way To Wear Shorts

Yes…yes. Here we go. I found this high-low dress two summers ago and thought ‘what if I do the half tuck and wear this with shorts?’ And it was over. As in, the search for the perfect summer outfit was over. No more trying and thinking. THIS. But…of course I can’t find the same dang dress or even the exact same shape this year. Of course. But check it out. We came really close, friends.

Current Version of My Favorite Way To Wear Shorts

Hooray! Though slightly different in shape, this cute dress from Amazon gives totally the same vibe as my high-low dress from years past. It’s still a little off-the-shoulder making it just glam enough to rev up the vibe of the cutoffs. The Pons sandals are nice and leg-lengthening, on-trend and comfy.

Outfit Details

Haola Women’s Loose T-shirt Dress – This very reasonably priced tee dress is super soft. Wearing size Small and it’s pretty oversized, especially in the neckline/shoulders. It’s available in a ton of colors besides black, too. This is a similar style with more of a sleeveless thing going on. I think it runs a little smaller though, so consider sizing up here.

rag & bone Shorts – I love love these and never thought I’d buy a ‘fancy’ pair of cutoffs. There’s just something amazing about them…the color, the wash, the soft fabric. They’re just good, you guys. Wearing size 28, one size up from my normal size.

Pons Avarcas Classic – Love how these break in, and the heel strap is just so comfy soft. They’re just a great leg-flattering flat sandal. Whole sizes. They will stretch a bit, so if you’re a half-size, I’d go down.


Have you tried a longer top with shorts? I’d love to see if there are other ideas like this that have been successful for you! Send ’em over.



Be sure to follow me on Instagram @elletrain to see daily outfits, what I’m currently whipping up in the kitchen, and of course, Sienna’s dance moves. And don’t forget about LikeToKnow.It for easy peasy shopping of the looks I’m wearing!


  1. Yes! I’ve been wearing a FP city slicker tee (sold out, boo hiss) that is a long tunic with these exact shorts. I tuck in the front part and keep it super loose. It covers the backs of my legs that I don’t like very much and adds some dimension. Throw on a cool necklace and sandals and call it good. I also have a few high low tees I got from Revolve a few years ago that come almost down to my knees in the back. And I just got this light cotton kimono from Anthro that I love for the same reason. Tie it in front with some shortie shorts and call it good. The two color ways I ordered are sold out but the pastel one is cool too. I love this look.

    *** Ignore the unconstructive rude folks commenting further up. Some folks have no manners. Geez.

  2. This was a useful post – I quite like this idea and probably wouldn’t have thought of it myself. I have recently started wearing shorts invisibly under shorter dresses though and I love it. It removes the icky feeling of sitting down to find your dress doesn’t quite cover your bum, so your thighs stick to whatever you’re sitting on, and means I don’t have to worry about flashing my undies if I’m on a bike, or playing with my kids, even if my dress is on the shorter side.

  3. When you posted about this look a few years ago, I immediately went out and got a maxi dress and extended the slits on the side to hip height to imitate this look! Its just something fun and a little funky and…cool, I guess. It works for me! Love it! Thanks for the inspiration. As always!!

  4. @ CS – My comment was referring to Jess’ rude comment — as in, I thought, “Really?” after seeing that someone would post something so rude here. I liked the post.

  5. Laura – apologies if my post (#2) wasn’t immediately clear. I was saying that I thought “Really?” that commenter #1 would post something so not-nice. I love the look. 🙂

  6. Really, is right. Sorry but that looks ridiculous. I’ve lived in 4 warm weather cities -currently live in FL and have never seen anyone walking around like that….

  7. I’m having a flashback. I went to a private school when I was a kid and wore a uniform. I hated skirts and dresses, so I always wore shorts underneath. I do enjoy experimentation and can appreciate your efforts. It’s just an odd look that hides your cute figure. Dress alone, cute. Shorts alone, cute. Dress and shorts together? Not for me! Chacon a son gout!

  8. The outfit is not ridiculous, your attitude definitely is though. So what if no one walks around like that? Since when does style have anything to do with wearing what everyone else does?

  9. And yes everyone is entitled to their own opinions and tastes, but being rude about it is unnecessary and intentionally mean. Some of these commenters seem like they’re still in middle school.

  10. I love this look. In fact, at church on Sunday, I saw a similar look on a friend but with skinny crops instead of shorts. My friend is in her 80s, petite, and is one of the most stylish women I know. I love that this style works for different ages and body types.

  11. Yessss. This is exactly why I keep coming back here, for Laura’s RAD punk style, which no other blogger nails in quite the same way. Thanks for the inspiration! ⚡️

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