Where WILL flattery get me?

They say flattery will get you anywhere, but will it really?

This week’s challenge was Ashley Tries Unflattering Clothes.  You (like my friends) might ask, “Ashley, why would you choose to wear unflattering clothes for a week?”  You might even through in a “What’s wrong with you?” for good measure.

Here are some answers to that valid question:

  • Sometimes this blog gets all serious and challenges like this can swing it back towards being funny.  I don’t take fashion very seriously, but it sometimes seems like I take Fashion Seriously.  Nope.  Funniness always wins me over.  Between a funny idea and a solid, practical plan, the funny idea will win.
  • My wardrobe contains some unflattering clothes and it was a good chance to evaluate whether they are completely unfortunate or secretly awesome.  I like to think all my clothes are secretly awesome, but deep in my heart, I know that is not the case.
  • I’m a glutton for punishment and I don’t know when to quit. (Laugh all you want.  It’s the truth.)
  • I have two great pairs of jeans that I wear all the time and both of them were in my laundry hamper last Monday morning.  So if I wanted to wear jeans on Monday (and I did indeed wish to wear jeans), the clean options were limited.  And looking through my clean jeans, I came across a wide-leg pair that I never wear. And since I wasn’t feeling particularly attractive at that point in the morning anyways – and since I hadn’t come up with an Ashley Tries challenge for the week – and since I tried on a drastically oversized top with the wide-leg jeans and then didn’t have time to change, the styling-unflattering-clothes-for-a-week challenge was born.

They’re all reasons.  But the last reason really kicked the week off.  The “stubborn and doesn’t know when to quit” reason kicked in mid-week.  That being said, I liked this challenge, because it was a true challenge and I didn’t know if it would work out.  There were a few times where it didn’t.

Here’s the look that kicked off the week:

This photo cracks me up.  This is how many of my outfit photos turn out, because I’m constantly trying to explain my thought process to my fearless photographer and my explaining photos are just lots of gestures and air quotes and concerned facial expressions.  This is a good week to give an extra loud shout out to my photographing friends, Sara and Lindsey, because this week was COLD.

I love a good pair of wide-leg jeans, but this particular pair is at least one size too big on me, so I needed the belt to cinch them into place.  I think they were designed to be that intentionally short culotte style, but since my legs are very short, they just slightly short on me.

As for the shirt, I found this gem of a blouse in a thrift store.  I cut shoulder pads out of it, so I’m guessing it is from the late 1980s or early 1990s.  Why did I buy it?  BECAUSE I LOVE IT.  It made from some sort of silky synthetic fabric, it has a rollicking rococo black and white pattern, it has a strange little bow tie at the neck, and it has so much material that I could probably wear tights with it and call it a mini dress.  It’s the comfiest shirt I own.  It is more comfy than my pajama shirts.  I wear this shirt with leggings on Saturdays and it’s the comfiest outfit in the world.  That being said, it is not a flattering shirt.  I know that.  But could I put two unflattering pieces of clothing together and create something amazing?  NO.  I could not.  So I threw a black wrap cardigan over the top, cinched the waist and went off to work with an okay outfit.

Jackets and cardigans cover a multitude of sins.  That was my biggest takeaway from this week.  With the cardigan, this outfit looks kind of pulled together.  Without the cardigan, the shirt kept bunching up at the waist and the jeans kept wanting inch down.  I like the idea of these jeans, but they are going bye bye.  Am I keeping the shirt?  Yes.  Because I love it.  Despite its tremendous volume and many weirdnesses.

Day 2:

I decided to tone it down for Tuesday and choose some pieces with more subtle fit issues.  The gray pencil skirt hits below the knee and the bomber jacket has a boxy fit.  I like them both, but I know that shorter skirts and more fitted jackets suit my short frame better.

This turned out to be my favorite outfit from this week.  It’s nothing groundbreaking, but the elongated vertical line of the skirt helped balance out the width of the jacket.  I was comfortable, I felt absolutely work appropriate, and the striped turtleneck gave it a little bit of color and pizzazz.  Also, it was the second day in a row tucking in my shirt and the second attempt was way more successful, because there wasn’t as much excess fabric to bunch up and move around.  With the shirt tucked in, the length of the skirt looked purposeful and interesting.

Will I wear these pieces again?  Absolutely.  Especially the skirt.  It’s a great skirt.  It came as part of a suit, but it fits well enough to stand on its own.

Day 3:

This was the low point of the week.  I think these are the most instagrammy photos of the week, but that’s because I’m trying so darn hard to make this dress look cool.  I bought this dress at a thrift store for the floral print.  Just the print.  I’m making a mental note to not do that anymore.  Since “my style” basically translates to “things I like”, I thought maybe this dress could be my style, because I liked the print.  Turns out no.  This dress looked like it was supposed to be on a tiny blond woman with an elaborate french braid and a floppy brim hat at her barn engagement photo shoot at sunset, not on me at work.  The dress looked confused.

For the morning, I wore this amazing wool sweater from Switzerland.  But by mid-day, I was sweating in the sweater and cold without the sweater.  The upside to this outfit was that I was warm on a very cold day.  When a dress is loose and flowing, it provides plenty of room for layering.  I had tights, boots, a t-shirt (because the dress goes too low in the front to be work appropriate), the dress, and then the wool sweater on top of that.  It was 12 degrees F and I was perfectly fine outside.  But I work inside, so I got overheated quickly.

A couple of friends told me to change when I went home for lunch, but I didn’t want to admit defeat.  (Have I mentioned that I am stubborn?)  I was not going to allow that dress to be the boss of me.  So I just switched out the wool cardigan for a jean jacket.  It helped a whole lot.

It still looks like I’m going to wander in a meadow somewhere, but the jean jacket suits the dress.  It gives the dress some shape and provides good color and texture contrast.  Am I going to keep this dress?  Nope.  For this dress to feel appropriate, I’d have to go wander in a meadow or stand next to a barn at sunset or become a singer-songwriter-country-folk-fusion artist.  But even if I did those all those things, I think I’d still want to wear something else.

Day 4:

By this point in the week, it was so cold that I was just going for warmth.  I can forgive almost any clothing for being unflattering if it is practical.  Practicality is the best.  So I pulled out all my bulky-lumpy-cozy-practical things.

Exhibit A:  This hat.



My sister knit me this hat and I call it The Flowerpot.  Even if fezzes become cool, this hat will still never be cool.  But I’m very fond of it.  It looks like a Tea Cozy.  But it’s for my head, so I guess it is a Noggin Cozy.  It kept my noggin very cozy on Thursday and I love how eccentric it is.  It matches my inner eccentricity.  I shall keep it.

Exhibit B:  These Croc Boots

Crocs are a much maligned shoe, mostly because they make human feet look like a Cabbage Patch Kid doll’s feet.  Fair enough.  But these boots have lasted me for years.  These might be ten years old.  They have pretty good arch support, they are comfy, they are warm, they are downright ugly.  I don’t wear them when I’m trying to look sleek or beautiful or important.  I wear my Croc boots when I want to stay warm in the snow and also feel like I’m wearing industrial strength slippers.

Exhibit C:  This coat.


Immediately post college, I didn’t want to spend money on a new coat, because a good coat costs a lot of money, so I would buy my winter coats at thrift stores.  Sure, they had ripped linings and crazy silhouettes and extravagant shoulder pads, but they all had personality and they were built for extreme cold.  This is one of those coats.  I need to replace the many missing buttons on this coat, but I love it.  It has served me so well.  It probably cost me five dollars and it has kept me warm and protected from the elements, so I’m very grateful for it.

The hats, the boots, and the coat all have memories and practicality on their side.  They may not be the most beautiful objects, but they are lovable and durable and oh-so-very practical.  They are what they are and I like them that way.

Day 5:

Friday was oversized flannel shirt day!  But in the Pacific Northwest, I think every day is oversized flannel day, so I didn’t stand out too much.  I can understand the appeal – flannel shirts are ridiculously comfortable.  It’s like wearing a big hoodie.

Overall, this is the most modern styling of the week.  This is kind of a Portland, Oregon look, with the high bun and the t-shirt dress and the flat boots.  I wanted to elevate the shirt and make it look more feminine, because Friday was the last hurrah for the challenge and wearing a men’s flannel shirt with jeans would feel sloppy.

Some thoughts that occurred to me this week:

  • I’m extra grateful for my clothes that fit well, especially my favorite jeans!  A good pair of jeans is a lovely thing.
  • A fitted jacket can streamline an oversized top or dress.  The black cardigan on the first day and the jean jacket on the third day helped out those outfits out immensely.
  • I’m the boss of my clothes.  The last thing I want to do is feel sorry for myself about my clothes or about how I look in my clothes.  It’s a waste of time.  When I put together an outfit, it’s not where I start that matters, it’s where I finish.  Don’t give up or get discouraged.  Get busy.
  • It’s just fine to get rid of a few things that don’t fit well anymore.
  • I’m not a fan of pastel boho maxi dresses.
  • I am a fan of practical coats and eccentric hats.
  • When I start to take my clothes too seriously, it comes from taking myself too seriously.  Taking myself too seriously usually stems from the sins of pride and worry.
  • I am so immensely blessed.  I have so much to be thankful for.  I’m thankful for my body, my clothes, my house, my job, my friends, my family, my life.  Most of all, I’m thankful to my Lord, Who has given me all these things and infinitely more.  He gave me my life.  I want to take everything He has given me and invest it and do my best with it.  How can I possibly complain?  The only response is gratitude.

Stay warm and have merry hearts, my friends!  Thank you for reading the ramblings of a happy little eccentric.  If you ever have any questions, send them my way.  I’d love to help out!

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