How to style shorts
Pushing beyond "shorts and a t-shirt" with a little help from contrast and tension
Welcome to the Esther Studio newsletter! I’m Carly, PhD, a marketing professor and jewelry designer living in the Midwest. This newsletter is my bold, sincere, down-to-earth take on personal style. Thanks for being here. Please subscribe so you don’t miss a post!
Shorts are a bit of a pain point for me in my wardrobe. I’ve had years when they’re all I want to wear, but lately, more often than not, I reach for… anything else.
I’ve heard I’m not alone in this, so what’s going on?
I think there are a few “upstream” and “downstream” issues at play. “Upstream” issues are inventory problems - when you’ve got the wrong thing. “Downstream” issues are styling problems - when you’ve got something that technically works, but don’t know what to do with it.
Considering that many of us are navigating one or both problems, in today’s post, I’m offering some solutions. First, I’ll break down some key considerations around fit and style. Second, I’ll craft a game plan for styling, followed by examples of shorts-centric outfits from my wardrobe.
Before we get started, please know that no part of this post is meant to read as “rules.” I’m just here to troubleshoot a bit and share some ideas. If you’ve got something going that works for you, I’m thrilled! I’m not the style police, I’m your style cheerleader.
With that in mind, let’s dive in.
Fit and style
There are three make-or-break considerations when it comes to shopping for shorts or auditing what’s already in our closets: size, shape, and fabric. If one of these considerations isn’t working with your shorts, you’ll likely be sacrificing comfort, which means they’ll go unworn. Conversely, if you can wear something without thinking about it constantly, that’s a win.
Size
Shorts tend to bring up “body stuff.” We go the whole winter with our legs covered, and then all of a sudden we’ve got to expose them to the elements! This can make us think and do some pretty unkind things to ourselves, which I’d love for us to collectively resist.
My biggest recommendation for shorts is to pick a generous size. Acknowledging that no one is looking at your size tags, and sizes are a figment of our imagination, do yourself this one favor and choose a size that gives you room to enjoy a burrito lunch.
I’m also thinking ahead to hot summer days. Having a bit of extra room will be the difference between enjoying some air flow or being trapped in your own sweat (sorry for the visual).
Shape
With so many silhouettes to choose from, look for cuts that work for your body shape. I don’t mean cuts that “flatter” your body shape. I’m talking about comfort here.
As a gal with muscular legs, I’m drawn to A-line denim shorts with a generous leg opening. This means they flare out a bit from the hips, rather than flowing straight down. As Devon observes, while A-line shorts might look oversized or baggy on a brand’s model, they look pretty “normal” on sturdy legs and feel much more comfortable than a slimmer pair.
Coverage is part of cut. Are you cool showing off a lot of leg? Awesome, I love that for you. If not, don’t try to force it. Buy a longer pair! Pay attention to inseam when you’re shopping online. The difference between five, six, and seven inches, for example, can mean the difference between feeling self conscious and feeling ready for anything.
Lastly, let’s talk about rise. All my shorts go up over my belly button, but something tells me it would be quite freeing if they didn’t. With lots of mid- and low-rise options on the market these days, it might be worth experimenting if you’re not sure what feels best.
Notice that none of my shape-related recommendations have anything to do with following trends. You don’t need to know what type of shorts are trending right now, or next week, if that sounds exhausting. You just have to know what works for you.
Fabric
Choose garments made of natural fibers, for reasons once again related to sweating. You won’t be able to enjoy the cooling potential of shorts if you’re encased in a fabric that doesn’t breath. Cotton, linen, and summer-weight wool are our friends!
Moving beyond this important point, though, are other fabric-related questions I can distill down to the matter of flow and movement. On one end of the spectrum, we’ve got denim. It’s sturdy. It’s not moving in the breeze. On the other end of the spectrum, a light cotton poplin that feels like a pair of boxer shorts will move with you and let some air flow. In the middle, I think of linen, or summer-weight wool. Each fabric will have its benefits and drawbacks, so make sure to select shorts made of fabrics that work for the way you want to feel and move.
Fabric types also translate into their own vibes. Heavier fabrics also tend to visually anchor an outfit, and can look sleek or polished, while breezier ones present a more carefree summer attitude.
The game plan
Let’s say we've all found some denim shorts that work for us. What next?
Shorts and a t-shirt is a classic combination for folks of all walks of life, and it’s still a viable option. Unfortunately for me, my brain yearns for variety and I find myself wondering, “Is that all there is?”
This is where I’d like to lean heavily on the twin ideas of contrast and tension. In art, when we’ve got two items, or an assortment of items, contrast refers to the visual difference between them. This difference, when used strategically, can create both interest and balance. In other words, it’s interesting when things don’t entirely match. Something that’s a bit off-kilter can actually feel right.
Contrast and tension apply to our outfits, too. When we dress head-to-toe in pieces that match perfectly, there is a lack of tension that almost reads as boring. Conversely, when we use a “pop” of difference - or sprinkle in little pops throughout an outfit - they create something really special.
As I re-commit to wearing shorts, I’m clinging to contrast and tension as a style North Star. That is, if my shorts are saying one thing, my top is saying something else. Then, I can tease out the themes in more detail with accessories.
There are infinite ways of thinking about contrast in an outfit, but consider this list (and examples) as a starting point:
Color: I love pairing light and dark colors for a high-contrast moment, but what about colors that don’t normally “go together”? Breaking rules is fun.
Fabric: We’ve got lightweight and heavyweight fabrics, or fabrics that are soft and smooth versus fabrics that are “nubby.”
Volume: I’m thinking about silhouette (the shape our garments create on the body). What about a slim-fit item on top, and something loose on the bottom? What about loose on the top and slim on the bottom?
Formality: Bring your dressy items down a notch by pairing them with casual items, and vice versa.
Essence: Take a style adjective - sporty, feminine, modern - and pair it with its opposite - polished, masculine, classic - for instant tension.
Finish: Matte versus shiny. Most of our clothes are pretty matte, so I like wearing accessories that bring a bit of shine. My everyday gold chains and earrings are reliable faves, but I also love metallic bags and shoes lately!
Thinking in terms of contrast and tension asks us to look carefully at the items in our wardrobe, really see what they’re telling us, and consciously use adjectives to describe it. This takes some practice, but it’s definitely worth it because it allows you to see your clothing as tools that you can mix and match according to your needs.
Let’s look at some examples.
A little lookbook
This week, in the name of newsletter research, I challenged myself to wear shorts three times, which is three more times than I’ve worn shorts in the past month. When I was styling each shorts-centric outfit, I used the principles of contrast and tension to create something that felt fun and interesting.
By sharing these examples with you, I don’t want to suggest that you dress like me. Rather, I want you to think about how you can apply these principles to dress like you.
Outfit #1
I based this outfit around a pair of long, summer-weight wool shorts. They’re a lovely mossy green color, and they remind me of my late grandmother, Trudy.
Because of this association, they feel quite “mature” to me. While I like these shorts in theory, my style leans more “playful,” so I tend not to reach for them - especially in these months when I’m not teaching. Of course, it turns out that the key to enjoying these shorts was pairing them with my more playful pieces!
Breaking down this outfit, it’s business on the bottom and “little kid” on the top. I chose the red nubby vest in part because I love how the bold color contrasts with the muted mossy green. The nubs also add visual interest to the shorts’ smooth texture. Note that I could have layered a plain white t-shirt underneath, but these green and white stripes continue the the playful theme.
For accessories, I chose to ground the colorful look with a black bag and shoes. A handmade bag charm and thrifted silver necklace keep things interesting by adding shine.
Outfit #2
My second outfit started with a pair of high rise, medium wash denim shorts with a raw hem. They’ve got an A-line shape that, again, reads as fairly straight on my muscular legs.
These shorts are really casual, owing to the raw hem, while my style tends to lean more “polished.” So, to bring the shorts more in line with my vibe, I paired them with some dressier items in my closet.
In choosing these items, I was conscious that denim cutoffs are pretty gender neutral, so I wanted the rest of my outfit to feel more feminine. So, you’ll see that my blouse has lace and embroidery details. The quilted elements on my lil vest are flowers, and we’ve got little lace trim too.
For accessories, my chocolate brown Mary Janes contrast with the light colors of my blouse and vest. The knotted detail of my bag adds texture against the smooth denim.
I had a bit of fun with my jewelry, too! The gold bow earrings and handmade gold watch necklace are super feminine, so I paired them with a chunky silver chain that I upcycled to make me look like I could potentially ride a motorcycle in my spare time (I do not). Here, we’ve got mixed metals and mixed essences.
Outfit #3
My third outfit revolved around a pair of washed black denim shorts in that same A-line style. I don’t wear a lot of black these days, so my instinct was to make the rest of my outfit feel lighter, with some pops of color.
Here, we’ve got a base of a simple white t-shirt, but I added a dressy vest over top to bring some polish. The scarf and shoes bring the color. I love pink and orange together!
For accessories, I brought in some shine with my belt, earrings, and tote bag. Since the clothing itself is rather flat in texture, the studs on my belt and perforations in my bag keep things interesting.
In terms of essence, the shorts and studded belt read “tough” but the blazer and silk scarf combo reads “office lady.”
This look was definitely a stretch in terms of what I would normally reach for - I know I would have preferred to wear a skirt here - but there was something about it that felt so creative and unique. As I was walking around, I felt very powerful.
Now, you try
If shorts have felt like a bit of a question mark for you, I hope this guide to buying and styling shorts gave you some new ideas! Ultimately, I don’t think we should ever force ourselves to wear anything that doesn’t work, but shorts can be so versatile and useful in the summer (especially once the weather heats up) that we might as well have a game plan.
Contrast and tension are also such universal principles that you can use them even when you’re not wearing shorts. The next time an outfit feels a little plain, consider what its elements are telling you. Then, add and subtract pieces from there. If something looks or sounds a little weird, that’s where the magic happens. After a while, when you dress with contrast and tension in mind, “weird” just becomes “normal” and you’ve got a personal style that’s all your own.
Thank you very much for reading! Before you go, I’d love to know about your summer wardrobe staples and how you like to style them. Tell me your thoughts in a comment or reply to this email so I can learn from you!
Like the idea of upstream and downstream problems 😊 my go to in summer is sleeveless shirts and linen pants.