Sunday, August 16, 2015

How I (Almost) Learned to Dress Like a Grown Up

I grew up in Durango, Colorado, one of the most beautiful towns in the country (in my humble opinion) but according to USA Today, my town was voted the "Least Fashion Conscious in America" in 1988.  No joke. Think about how bad a town of people would need to dress in the 80s to be considered the worst in America!  There were references to our seemingly exclusive love for North Face, Padagonia and fanny packs.  In our defense, we were hours away from any major cities and our shopping options were Walmart, JC Penny's or the thrift store.  Don't believe me? Check out the picture below.  Clearly I'm very upset about 1) looking like a boy and 2) the business in the front and party in the back.
Embracing my Durango spirit, I've always struggled with fashion.  My sister has an incredible fashion sense that she tried desperately to impart to me, but it never stuck and she gave up on me long ago.  I've studied my friends, looked to blogs and celebrities for tips but nothing clicked.  It probably doesn't help that I hate shopping. If you already read my Confessions of an Unconventional Wife post, this probably comes at no surprise.  I get too overwhelmed by uncertainties and questions to really figure out how to put together an outfit beyond copying the exact outfit the mannequin is wearing.  I'm 32 years old and I desperately need someone to teach me how to dress like a grown up.

This blog has been a huge source of self improvement for me.  It has motivated me to write consistently, make improvements in my home and schedule and has created new relationships through organizing projects.  It felt like a natural next step that I should use the blog to try to improve my (lack of) fashion sense as well.  And the person who was going to guide me on this journey? My adorably, trendy and VERY patient friend Heather.  

Heather is the perfect female specimen.  She is crazy smart, values her family emensly, loves sports and shopping, is very athletic, a kind and thoughtful friend and is one SHARP dresser.  I could go on but you get the point, she rocks!  I have a good number of friends that could have given me tips on how to dress but Heather is also very organized and a natural teacher.  Even though she lives a couple states away from me now, I knew she would be the perfect person for the job.  I reached out to see if she would be willing to help and she happily agreed to assist this poor unfortunate soul.  

So how would this work? What did I hope to accomplish and how would we get there?  My basic goal was to get rid of all of my clothes that were outdated and were not doing my body any justice.  I've had two kids so I've gone through a variety of sizes over the past couple of years.  I'm also always struggling with my pack rat tendencies so I guarantee there are pieces of clothing in my closet from high school. Secondly, I needed someone to tell me what I'm missing from my wardrobe.  I don't want to spend a ton of time or money buying clothing.  Which means I need guidance on finding versatile pieces that could be used across a variety of outfits. 

We set up an hour Skype date (not enough time) and dove right in.  As with all organizing projects, we needed to take a look at everything we were working with and purge.  The only way for Heather to accurately evaluate my clothing was for me to try on every single item.  Yes, I know, she should win a friend award.  It was a little awkward at first, standing in front of a computer screen modeling clothes, but I was happy to discover that my intuitions on most of my clothes were on target.  The problem is that I was lacking the confidence to get rid of those crappy clothes.  And by taking out all my clothes at once, it was much easier to see my fashion shortfalls and how often I was making random impulse purchases.

By the end of our short hour, we were able to make surprising progress.  I had a gigantic donate pile, a closet that you could actually see and reach individual clothing items and a list of suggestions for what I needed to purchase.  Everyone's sense of style is going to differ and we focused mostly on my work clothes but here are a few nuggets of wisdom that Heather bestowed onto me:

During our Skype session, I mentioned how a lot of my tops made me feel frumpy and immature.  Heather's solution?  Tucking.  And it is true, tucking almost any shirt can make your outfit look cleaner and more professional.  Though tucking is not for everyone.  I mentioned my newfound knowledge to a friend at work and she said, and I quote, "Tucking is for skinny bitches." She had a point, I've had two kids so tucking a shirt into my pants emphasizes my "mom belly". The key is to play around with different top and pant styles to help determine when it makes sense to tuck and when it is best to leave the tucking to the "skinny bitches."

Finding Your Basics
I love a piece of clothing that adds a bright pop of color to an outfit but over time it seems that I have purchased a whole lot of pops and no basics.  I have a few skirts but not a single black, grey or brown one.  Which isn't to say the blue skirt doesn't work, it just limits the versatility of my clothes.  Before you go off and spend money on another fun orange blouse, make sure you have some neutral colors too.  The purchase may not be as fun but being able to get ten outfits out of one piece of clothing is a lot of fun, especially on your wallet.  You can always add your pops of colors with an accessory or two.

Accessorizing: Belts, Necklaces
I can't tell you why but for some reason accessorizing outfits with a belt or jewelry has been a complete mystery to me.  I just didn't get it.  Every belt I owned was chunky, but not in a good way, and I'm pretty sure they were from the 90s.  Also, we (myself and my wardrobe) didn't know the meaning of a statement necklace.  So it shouldn't come as a surprise that shopping for these particular items became quite an adventure.  Please, let me share my many, many shopping errors in hope that you won't make the same.

When buying belts, plan ahead.  You will end up buying eight different styles of belts and take many trips to the store to return most of these belts, if you don't know what you need for your wardrobe.  Heather showed me two different styles of belts.  A wide decorative belt and a super skinny belt.  Each had a unique way that it helped accessorize an outfit.  The thick belt could be used to create a waste for a flow-y dress, cardigan or loose-fitted shirt. The skinny belt should be used more as an accessory than to actually hold up your pants.  It can belt a cardigan, a dress or even add a little color to an outfit with a lot of neutral tones.

Even with all the unnecessary belt purchases, I still did better in that department than with the necklaces.  It wasn't that I couldn't figure out what to buy, that part was easier than I thought and I ended up getting some really versatile and fun necklaces.  According to Heather, there are very few statement necklaces that are too over the top if you are accessorizing correctly.  My problem was that I couldn't seem to keep them on my neck.  I bought two different long necklaces and had them snap in half within a week of buying them.  The first one got caught on my kitchen cabinet and broke and the second one got caught around my daughter's head and broke.  The whole situation was very disheartening but I learned two very important lessons.  Number one, invest in some jewelry string/wire to easily fix your necklace if they do break and lesson two, take your necklaces off when you get home.

I didn't even attempt to by any other accessories like a bracelet or purse.  Too soon.

Pointed Toe Wedges
When Heather told me I need to add some pointed toe wedges to my wardrobe, I thought I heard her wrong.  I even asked another friend if they had heard of this type of shoe and they also thought I had heard her wrong.  Maybe she meant to say 'Peep toe wedge'?  But no, as usually, Heather is just more in the know than the rest of us and shortly after she told me to buy the shoe, I saw some fashion article talking about the new trend of pointed toe wedges.  I have to be honest, I've never been a fan of pointed toe shoes.  I think they make you look like you have witch feet.  But if I truly want to try to improve the way I dress, I was going to need to trust Heather's advice.  It took a while to find a pair but when I did, I finally understood why they are a must in my wardrobe.  The pointed toes make your legs look long and slender and the wedge makes them more comfortable to stand in all day.  Can't argue with that!

I'll be completely honest with you, the first day that I went shopping, I just wanted to get the whole process out of the way.  I took my one year old daughter with me to Target (huge mistake) and bought about $400 worth of clothes.  When I took them home and tried them on, I was devastated to see that I had reverted back to my old habits and compromised on my clothing choices so that I could get out of the store quicker.  I then proceeded to return around $300 worth of the purchases and started over.

What I ended up purchasing and where:
  • Necklaces at Target
  • Belts at Target
  • Long sleeve blouse at Target
  • Cardigan at Target
  • Pair of pointed toe wedges at Marshalls
  • Light jacket at Marshall
Whenever you attempt to learn a new skill, you need to evaluate how much you have learned, right?  That being said, I sent Heather pictures of a few of my outfits and asked her to grade me.  As with any good teacher, she was fair but honest.  
"Love this blouse and necklace combo (you apparently DO own jewelry!). But the black pants, sweater and shoes are just a bit too safe together. Swap any of those three for something in grey family and you would have been spot on." 
"Love the monochromatic look broken up with a metallic skinny belt. And the tucked shirt (which I know you were reluctant to try) really highlights your figure. But the look would have been more complete with a pop-of-color bracelet or earnings. And I have no words for what is going on with that canvas carryall. (The + was for the head tilt and sass.)"
"Love the belted cardi over the dress and the mix of blues with a neutral shoe. But the cardi would have been better as a v-neck and this outfit is practically screaming out for a statement necklace." 
"I love a belted dress and this look really flatters you. But again the color palette is a little safe. The belt would have been great in basically any other color besides black and playing with another material (like a metal or woven) would have been a nice contrast. The outfit is also lacking accessories (shocker)." 
Her general advice was this, "The oft-quoted fashion advice from Coco Chanel is: 'Before you leave the house, look in the mirror and take one thing off.'  Ignore this completely.  In your case, look in the mirror and put one more thing ON (that is not black)."  

I clearly still have a lot to learn about color palettes and accessorizing but I am proud to report that on a recent trip to Marshalls I picked out five (yes, FIVE!) shirts that received the Heather stamp of approval.  Take that, child-hood me rocking a North Face jacket and fanny pack!  I still need to purchase a few key pieces of clothing like a nice blazer and a black pencil skirt but at least I now know what I need and can keep an eye out for the perfect find.  Knowing how to dress like a grown up isn't going to magically happen overnight but a little bit of guidance has created the extra confidence I needed to finally belt that cardigan and rock that statement necklace.