Ashley Tries X: Dress Over Trousers

One of the fun things about being an amateur fashionista is that people occasionally ask me for advice about clothes.  You can’t even imagine how tickled I am when people message and ask how to dress for a new stage of life or how put together an interview outfit or if I can help them pick out their wedding dress.  Yes yes yes yes yes.  I feel like I’ve gotten a reputation for knowing about clothes just because I won’t shut up about it and by being okay with wearing strange combinations of things.  So far it’s really paid off, because people keep asking me questions on a subject that I want to think about anyway!

The other day I got a question from a friend asking whether it was a fashion crime to wear jeans under dresses.  I sent off my preliminary thoughts right away, but I decided to go one step farther.  I’m using the question as an excuse to kick off a question-based series called Ashley Tries X.  Send me a question about a tricky trend – is anybody else confused by this culotte renaissance?  Or send a question about that one piece in your closet that never gets worn, because it doesn’t play well with the rest of your clothes and you don’t know how to style it.  Ask about fashion crimes.  Ask away!  My fate is in your hands.

So here’s the story on my dress + trousers day:

Friday morning, I was getting ready for work in my ordinary morning haze.  I honestly think the Morning Haze has more to do with my fashion sense than anything else.  It’s easy to make bold choices when you are half asleep.  And I don’t like strong light when I first wake up.  This leads to crazy color combinations, because everything matches in the dark.  Anyways, as I sifted through my t-shirts and jeans, I discovered a knit leopard-print dress in the same drawer.  Finding it mixed in with all the trousers and shirts reminded me of my friend’s question about layering dresses and jeans.  My morning-muddled mind asked WHY NOT?

So I layered the knit dress over skinny military-green trousers and added a jean jacket.  I didn’t wear jeans, because my jacket was already denim and it seemed redundant.  (It probably would have looked better with jeans and a different jacket, but I’ll take that into consideration for next time.)  This decision took about two minutes, because I was hungry.

This was not my first time at the dress-over-jeans rodeo.  Babydoll dresses over flares used to be my scene circa 2005 to 2010.  It was fun.  It was playful.  The dresses were MADE to be worn over jeans.  It was the water I swam in.  I think that’s one of the reasons I felt super young in this combo – it kicked my memories back to a more Lizzie McGuire age.  Young and informal – not un-cute, but I didn’t feel grown up.

During the day, I was very conscious of the outfit’s proportions.  (…If the dress was a little bit shorter, it would be better…..if the jeans were tighter at the ankle, it would be better….)  So if you want to try this, make sure to use your most fitted jeans – the tighter the better.  To look modern, the jeans should be taking the place of leggings or tights.  Don’t wear a pair of jeans that makes the dress look lumpy at the ankle or at the waist.  The green trousers I wore fit me great from the calves up, but they get a little bunchy toward the ankles.  The problem was that the dress covered up the places where they fit well and highlighted the places where the fit wasn’t great.

But there were definitely parts of the combination that I enjoyed – Friday was a crazy weather day and as I walked outside, the updrafts were pulling a Marilyn Monroe on my skirt.  It was almost impossible to hold down all the points of a skater skirt when the wind has different plans.  So I held down that skirt the best I could, but it was comforting to have something more substantial than tights to keep me covered!  The skirt is fairly short, so I would normally wear the dress with tights or leggings, but it’s nice to have another option as well.

It was an interesting balancing act between how I act in a dress and how I act in jeans.  I enjoyed the mobility and ease of not having to worry about my skirt riding up, and I would find myself not being as careful sitting down or leaning over. But then I would remember that I had a dress on and cross my legs like a lady.  Again, I felt really young – I remember being little and wearing a dress meant you had sit up and cross your legs and be careful and not turn all the way upside down on the monkey bars.  But I’m grown up now – I’ve learned how to handle dresses and I really like dresses.  It’s second nature now.

It made me realize that I carry myself differently when I’m wearing a dress.  Then when jeans enter the equation and the dress takes the place of a long top, it’s a little confusing to know how to behave in it.  I came to the conclusion that even with the added coverage, if you’re wearing a dress, wear it like a dress.  Don’t put things in your pockets.  Don’t sit with your legs open.  Behave like a woman, not a kid – which may seem like a no-brainer, but I had to remind myself more than I thought I would.

Conclusion:  I would wear a dress over trousers again, but not with the same clothing combo.  For this layering to work, the proportions are the most important part.  I didn’t think about how my trousers fit at the ankles until I got to work and then I noticed it all the time.  I wouldn’t wear it on a day when I have to be in charge of something or need to do something very adult (like file taxes or go to the DMV), because it made me feel young and informal.  But there was a certain ease to it that I really enjoyed and I loved how different it was.

Who should try this:  I know some women who feel really uncomfortable in dresses, because they feel like they have no range of motion.  This would be a fun idea for them to try, because it gives them the security of wearing jeans, but adds the option of cute and comfy dresses.  It would also be great for the moms who tell me, “If I wear a dress, my kids are just going to pull it up and hide under the skirt!”  If they are worried about wearing dresses, because they don’t want to accidentally flash everybody, this could lessen that worry  It’s also a great way to combine clothes you haven’t worn in a while – that slightly-too-short dress in a great print will pair nicely with those slightly-too-tight jeans that you still love.  I’m not going to rock it every day, but on a blustery day or a I’m-in-the-Mood-for-Something-Different day, I think the dress-over-jeans will ride again.

Comment if you have any ideas for what I should try next! 






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