How to wear denim cut offs without looking like a teenager
Alternatively: How do I wear denim cut-offs and look more interesting than I did last year and the year before and also the one before that? ALSO SOME VERY LONG WIND
The more I write about how to get dressed, the more clear it becomes that I’m always trying to do the same thing: reflect multiple parts of me. Do you find that’s the case for you too? It’s like, I can’t just settle on wearing a tank top with denim shorts when it’s too hot for anything else because even though the combination would be an adequate solve to the problem of ventilation while engulfed in a blanket of steam, it doesn’t seem worth the possibility that I could be mistaken for the sum of this one, finite thing.
I wonder if this is always what has motivated my style and pursuit of getting dressed. What I have been so relentless about expressing — what parts of me have been misunderstood or represented or simply unheard, why words don’t seem like the utmost explication, and why, even after all this time, I keep coming back to it.
It’s the metaphor of style as character and clothes as these expressions of it, which ringers truer the longer I think of it.
If I were putting the core features of my personality on paper, I’d probably draw an x and y-axis then start putting features in each of the quadrants.
The features would live on this sheet of paper, organized within the compartments of their quadrants, which would be an organized way to think about it but then I’d be like, Now what? All of the shit that makes up who we are commingles in real-time. It’s way more chaotic. There are no compartments. I am the axes and all the things that plug into the different quadrants. The thought doesn’t empower me, I start to melt, the axes drip into themselves and whatever was in those quadrants now float aimlessly.
But then I go to my closet. I think about what I’ll wear, but really how I’ll present myself on this day. I consider what’s interesting me, where I’m going, who I’m with, what I can offer, what I can take; these features ladder up to a narrow but meaningful snapshot of personal past experience, current circumstance and desired future. The axes stand back upright. Style becomes the axes. And the clothes are what’s in the quadrants.
When I do not forget this is when it gets interesting — I start to adjust the dosages: how much of what’s in quadrants will be conveyed through what I am wearing? What’s in the those quadrants stays the same, but I regulate how much I show. And it changes everyday, or it never changes, or it changes sometimes — whatever feels true.
I bring all of this up mostly because from the prompts you’re suggesting and convos we’re having, it seems many of us are trying to balance these parts of ourselves that expand and contract and mutate and splinter in this tactile language — fashion, which for whatever reason, we are drawn to and today, it lands us at shorts.
Shorts!
So, how do you wear them without looking like a teenager, but also just kind of like you’re not exactly who you were last year at this time?
To not look like a teenager I maintain:
Your best bet’s to subvert the concept. Go in with a garment that reminds you of someone in your life who embodies maturity, wisdom, elegance — however you define not being a teenager. For me, the person isn’t real, but she wears a lot of tweed. It’s a jacket, often, and collarless. It swings, maybe she does too! Emotionally stable and curious, the wearer doesn’t take shit out in misguided places — knows where to direct her feelings for landing when they’re still flying but also doesn’t suppress (i.e. shoot them down) because she has way too much self-respect for that.
Life is too short, she says. Buy the damn vintage jacket.
A few things to consider here: denim cut-offs are great when you’re trying to make your “fancy” clothes look less fancy. Like you wear a refined shoe and it creates a solid balance against the frayed hem. The jacket does the same thing. I like adding a t-shirt or button-down so the shorts have a companion in shit-not-together-ness. What’s cool is that in some ways, this is actually a three-for-one outfit:
You can wear the shirt or the jacket solo and it works just as well. The shorts are a dark enough blue in their shade of midwash that the white button-down gets to have an identity of its own — they contrast starkly, can manage different conversations at a bar but still respect each other in this interdependent way. They know they like to be with each other but don’t feel like they need each other. Omg, I wonder if this is why I don’t like wearing sets? It hits too close to home! Codependence on sparkling display.
Anyway, if I take the shirt off and just wear the jacket, that works too; it’s moodier, less casual, slightly risky, but who among us does not yearn to have our naked bodies rub up against decades old silk in the blazing heat now and then?
To not look like yourself last year, I don’t actually know how to advise you in literal terms because I don’t know what you looked like last year, but here are the factors that I considered when evaluating my own desire to do the same:
Technical style
Style of shorts, hemline: Frayed? Stitched? Ass-short?
Style of shorts, waistline: High (and midrise) or low?
Color of denim: Black, white or blue? Shade matters too! Faded, medium wash, or dark like your shadow side?
Hard conditions
Occasion: Where are you going, what are you doing?
Audience: Who will be there? Do you feel confident in this environment? Can you take a risk or is it more like, you need your clothes to hug you (either is totes normie!)
Transport: How are you going to get there?
Soft conditions
Insecurities to conceal: what don’t I want to convey? Or, you know what, this is pretty cynical. How about instead:
Forthcoming securities to will into existence: The ways you want to be.
Confidence points to expose: The parts of yourself you love, accept, want to celebrate all the time.
Lately, I am attracted to shorts that aren’t frayed hem, or actually, it’s more like, shorts that are rolled over. I had a pair of Levi’s that were midrise and wash, like a perfectly stark denim blue, orange stitching and label; they flipped over at the hem, which exposed two large pockets and they were tight around my waist and butt. I gave them away in 2017 because every time I sat down, I was sure that day was going to be the one I made it into the world record book for having my vagina lips sliced-by-inseam. They were oppressive and I yearned for freedom, but still I fantasize about what would have been if they’d fit better. It doesn’t matter now, I hope they’re in good hands and being worn with fupalicious abandon.
I found the pair (above) from Moussy recently (if you have a pair of slightly oversize, a-line shorts, that are somewhat longer, you can probably just flip the cuff hems and call it a new look. Or you can cut some old jeans and do the same thing — just make sure they’re a wider leg!), a good counterargument to last summer’s way to wear denim cut-offs without looking like an outdated version of myself.
I started from the bottom, with the shoes. I didn’t expect the shorts would feel more casual than the ones with a frayed hem (I think it’s the wash) but that’s what compelled the summoning towards satin footwear. They’re also this vague a-line (meaning they swing out). Shirts either tucked in or fitted tops look best with this shape. If you like belts, or at least want to wear them more, here’s a good place to test that pursuit. I also think their shape, which sort of demands a tuck in makes them a good contender for cut-offs to wear with big boobs? Can’t speak from experience, so you tell me.
I styled this green marble print quilted vest (above, from Les Cactus Uniques) over a red-based floral print, both cotton and pretty casual — I’ve been hankering for color lately. The shoes are so formal (satin and jewel-encrusted) that they hold court for the sum of their quadrant (see, the intro was worth it!). As a general rule for cut-offs, I tend to choose refined sandals that are slingback/have backs (evidenced in first look) or a closed toe that is narrow but never exactly pointy. THURSDAY’S BREAKDOWN IS ALL ABOUT SUMMER SANDALS SO WE’LL GO IN DEEPER THEN
On the topic of closed shoes, and in a final bid for what to wear, here’s an extremely casual outfit:
I got the idea from Mary-Kate Olsen, who I saw at a farmstand last summer. She was wearing what looked like a much more tattered version of these shorts with a tank top and these exact shoes (from her own brand) (The Row). It’s actually what compelled me to buy them. I wore the outfit plenty last summer, but don’t think of myself as a former “me” in it.
Occasionally you’ll find that iterations of us remain exactly as they were. Exactly as they are. Until that is, they don’t. Still here for now but signing off yours truly,
Weird Al Yankovic
Thank you for this ! I never know what to wear with denim cut shorts in Town! I'm afraid I'm too old to wear it and at the same time... I don't care!
Loved your bag post today! Didn’t know where to comment on it. Can you give an recommendations on how to find cool bags on Etsy or other sites? Vintage? Thanks!!