I got a request to try wearing denim on denim this week – this one has been great, because this is an area where I make a ton of arbitrary rules for myself. When I create these fashion barriers for myself, I rule out a lot of outfits from the outset. When you worry less, suddenly your wardrobe contains a whole lot more potential outfits. (Funny how that works!)
Outfit 1: Denim Shirt + Jeans
I only own one denim shirt and I don’t wear it all that much, partly because of all those rules I make up (more about those as we go along), but also because it is a buttondown. Shirts that button tend to gap on me and I sometimes (okay, most times) don’t want to mess with them. The reason I bought this particular shirt was that jeans shirts seemed to be all the rage, but I didn’t think you could wear a blue jean shirt with blue jeans. So I bought a gray one.
This was my most apologetic outfit this week – I wore black jeans with a gray denim top and I felt super boring. That’s why I added a busy jacket – it has quilting detail, contrast zippers, and a bird print. I also wore red lipstick, which I don’t usually wear. There’s something about gray that makes me feel like I fade into the background, like I’m a cement block. So the outfit didn’t start out promising for me, but it grew on me.
I started out not liking how basic the the black and gray jeans looked, but once I got over that, I saw that it was a great blank canvas. It provided a backdrop for drama – the jacket and red lipstick were the stars of the show. Simplicity is not my default, but it can be refreshing. It was a good start to the week, because it made me loosen up and change my mind.
Outfit 2: Blue Jeans + Jean Jacket
After easing into the week, I decided to break the first and most important of the Ashley Denim Rules. Don’t wear a Canadian Tuxedo. What is a Canadian Tuxedo? It’s a blue jean jacket and blue jeans and I don’t know why it is called that, but it is. I don’t mind the look on other people, especially farmers. Farmers look legit all the time. That’s because they care more about the functionality of their clothes than how their clothes look. I care so much about how my clothes look that I sometimes give up functionality altogether. SOME OF MY JEANS DON’T EVEN HAVE WORKING POCKETS. Farmers wouldn’t put up with that for a second. Anyway, I’ve always felt the Denim Squared look is one of those looks that can only be worn successfully if you don’t think about it. And I think too much. Obviously.
I made it a bit more girly with a dotted tee, my grandma’s flower necklace, and pointed flats. I admit the necklace was a distraction maneuver (DON’T LOOK AT THE JEANS, LOOK AT THIS NECKLACE). But it wasn’t really necessary – apparently nobody but me cares if I wear blue on blue. Actually, people liked the look, and by the end of the day, I liked it too. The nice upshot of all of this is that I won’t worry about throwing on a jean jacket over jeans. Denim jackets are the perfect weight for spring and I probably will be wearing this one a lot in the near future!
Outfit 3: Polished Denim
By day 3, I’d already exhausted my denim top options, so I asked my friend Sara to lend me some chambray. What are friends for?
This blue chambray top had a beautiful tailored fit, so I paired it with dressy pair of jeans – they’re a J. Crew pair I found at a consignment store. After adding print in the first two outfits, I felt like I should keep everything simple and streamlined. The fit elevated this outfit. The darts and shoulder style give the shirt a 1940s feel and very dark wash jeans always feel more dressy to me – the combination felt like a cool mix of conventional and modern.
Black heels were in keeping with this outfit – the peep toes give them a little 1940s vibe, but they are practical and solid. That’s how this whole ensemble made me feel – professional and put-together, but with a bit a vintage, a bit of attitude, and a killer fit. Nothing much added, nothing to jazz it up. I guess good fit is my comfort zone. If something has a fit that I love, I don’t add distraction pieces.
Outfit 4: Patterned Denim
This dotted denim shirt also belongs to Sara and it is so comfortable. I need to keep my eyes open for a chambray shirt, because I see their value now. The dot pattern and the looser fit of this shirt made it more casual than the last one, so I decided to emphasize the playfulness with some pattern mixing and a light color scheme. By this point in the week, I was comfortable with denim on denim. Isn’t that cool? Four days and my stubborn little opinions changed.
This outfit felt cute, comfy, easy-breezy. I also want to give a shout-out to my great old Payless shoes. These babies are workhorses – as it turns out, mushroom color goes with everything. Who would have thought?
Outfit 5: Rufflepalooza
On the last day, I returned to my own jean shirt, because I had exhausted my top options. Since I’d already worn the top, I wanted to style it completely differently. This denim wrap dress is pretty cool – it was a Ross find from a few years back. In the summertime, I’d normally wear it over a bright tank top. In the wintertime, I’d style it with a black turtleneck and boots. But nothing this week was a normal styling choice for me, so I decided it was time to go big or go home!
The wrap dress gave the gray jean shirt a different vibe – it was reminiscent of a uniform, which I don’t mind at all. The whole look leaned towards a Dust Bowl / Great Depression aesthetic, so I couldn’t wear ankle boots or oxfords (it would have been too on-the-nose referential). So I pulled out the spiked wedge sneakers. These shoes bring a smile to my face and that’s what this outfit needed. It needed some humor and eccentricity.
I’m really glad I tried this one – it pushed me out of some assumptions that I didn’t even realize were issues. Why is there such a difference between What Other People Wear and What I Wear? I never minded when other people wore denim on denim on denim, so it’s hilarious that I had so rules for myself. It all comes down to self-consciousness. One major thing I realized this time around is that I’m deep-down afraid of being a Boring Person. That’s why I wear clothes that make me feel like an Interesting Person. So when I have a simple outfit on, I’ll put on red lipstick or a crazy necklace or a huge scarf. Just to feel like I’m seen. I try so hard not to blend in with the wall, but people see me no matter what I wear. They notice me more than my outfit. That’s a big comfort.
Please keep sending try requests! Thanks to Medora for the denim on denim question.