Ashley Tries: Denim on Denim

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.



One thought on “Ashley Tries: Denim on Denim

  1. I saw a link to your blog in the comments on Blog & Mablog. I’m so glad I clicked through, because this is really fun! Thanks for sharing your ideas. It’s inspiring me to think more creatively with what I have in my closet. 🙂

    Liked by 1 person

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