Off The Cuff: I Need A New Wardrobe For My New Life

new life, new look.

Dear Winona,

Over the past year I’ve made a lot of changes to my life: new relationship, new city, new friend group, new outlook. I feel better than ever in so many ways, but every time I look in my closet I’m reminded of my old life. I’m starting to feel like I’m wearing a costume of my old self when I get dressed, but I don’t have the money to buy a whole new wardrobe right now. How do I go about changing my look to match my new life?

Signed,

New Me, Old Clothes

Dear NMOC,

Making a big life change is often followed by the strange and frustrating feeling that your current wardrobe isn’t YOU anymore. I’ve totally been there, at many different points in my life: after high school, again after college, after moving across the country, after swearing off fast fashion, after losing weight, after gaining weight, after turning 30.

Phew! I’m exhausted just thinking about all those style shifts. But after going through so many, and managing them with varying degrees of success (not successful: the time I gave away my amazing vintage clothes collection because I was trying to be a minimalist, which lasted for about a month), I’m ready to advise. Here are a few tips for managing a major style transition without going bankrupt/insane:

Force yourself to slow down.

You’ve already done the real work it takes to change your life: at this point, having a wardrobe that aligns with your new lifestyle is just the cherry on top. Keep that perspective in mind as you start the process of creating a new wardrobe. Don’t rush it — impulsive shopping decisions almost never pay off in the long run. Give yourself time to fully settle into and understand your new aesthetic. What looks do you feel most drawn to these days? What styles of clothing feel most “you”? Be practical, too: What do you wear the most? What do you actually need? Build your new wardrobe slowly and methodically. Trust me, you’ll be glad you did.

See old things in a new light.

Let’s say part of your life transition included leaving an office job and working for yourself, so now you have a closet full of business casual duds and nowhere (and no desire) to wear them. Chances are you won’t need those dreaded polyester slacks anymore, but many items — especially basics — are much more versatile than you think. Try dressing down your pencil skirts with graphic T-shirts or slouchy sweaters. Layer blouses over flowy dresses to create a totally new look. That basic ponte dress you wore to the office every Tuesday and Thursday? Pair it with a funky belt and sexy boots and it’s ready for a Saturday date night. Have dresses and skirts hemmed a few inches higher to change their look, or get crafty and change out buttons or add a colorful lining to jackets. Get creative! Chances are, with a little tweaking, your current wardrobe could be transformed into your dream wardrobe.

Hold on for one more day.

Learn from my tragic vintage clothing purge and apply some Wilson Phillips lyrical wisdom to your closet cleanout strategy. Instead of packing up everything you don’t want anymore and driving it straight to Goodwill, put the items in a box and set it aside for a month or two. Give yourself a chance to miss them or realize you need them. See if there is any way to work those old pieces into your new wardrobe, if your aesthetic shift turns out to be less dramatic than expected. After a few months, sell or donate whatever pieces are still left in the box.

Get thrifty.

Is it tempting to hit up the mall and buy a perfect, complete wardrobe in one fell swoop? Yes, but it’s also prohibitively expensive for most of us. Save money by scouring thrift stores first. You’ll save money and be kinder to the environment in the process. As an added bonus, thrift stores have so many different styles, brands, and fashion eras packed into one space that you can try on (literally) a huge variety of looks at once, which is a valuable exercise when carving out a new signature style.

Treat yourself to one investment piece.

When I moved from Portland to Nashville a few years ago, I wanted to throw away all my clothes and buy a whole new Tennessee-centric wardrobe, but alas, I couldn’t afford it. Instead, I saved up and bought myself a really nice pair of leather ankle boots. They instantly imparted a Nashville vibe to all my old outfits, and spending a chunk of change on them felt good — it felt like I was investing in not just my new look, but my new life. Don’t go crazy, but do identify a garment or accessory that will help redefine your new wardrobe, and save up for a beautiful, well-made version of it. It’s hard to change your life for the better; if you can afford to celebrate that change with a dress or a hat or a fabulous pair of new jeans, more power to you.  

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