Getting Dressed: How I Redesigned My Wardrobe

Rent the Runway, Trunk Club, Stitch Fix, Tradesy, fancy schmancy, secondhand—I tried just about everything so you don’t have to. That is, unless you want to too.

I had a lot of wardrobe shame when I moved to San Francisco. My suitcase was packed with clothes from previous lives: thick, dark H&M sweaters from Berlin; bright, breezy dresses from Atlanta; wool dresses and thick stockings from Boston.

Nothing worked for the weather, and everything felt a little off. It’s taken me a few years to get my closet in order, but now I finally feel good while getting dressed. Here’s what I’ve tried and learned.

Goals

This is what I was trying to solve.

  • Dress for the weather. It’s often warm in the sun, but cold in the shade and everywhere after 4pm.
  • Look sophisticated.
  • Feel comfortable and authentic.
  • Sweat less, and hide sweat when necessary. I had a lot of nerves at work for a while, so this was a big concern. I’m much less sweaty these days, though, thank goodness.
  • Fit in. Just being honest here—I’m not really a statement maker when it comes to clothes. I also wanted to deconstruct the components of the San Francisco tech uniform. More on that below.

Resources

This is what I had to work with.

  • Money — I’ve got a dedicated clothing budget, which grows and shrinks as my priorities shift.
  • Time—Recently, I spent several months working on service experience design, so I had extra time and incentive to experiment with new services. Before that, I generally enjoyed devoting some weekend time to shopping or trying new things.
  • Interest—I love learning about brands, styles, and materials, so while my quest was sometimes fraught (in terms of fit or identity), it never felt like a chore.

Services I’ve tried

For clearing out — ThredUp

This is the easiest way I’ve found to purge my closet. And if you’ve read Marie Kondo, you know this is one of the prerequisites to keeping calm while getting dressed.

You can request a bag from ThredUp, and they’ll send it right to your mailbox. Fill the bag with things you can’t wear or don’t like and send it right back. You can either get a donation receipt or a credit to use on clothes from the ThredUp store.

Tips:

  • The donation bag is pretty big! Use it to do a really thorough closet purge.
  • Don’t get so extreme about purging that you end up with no pants. If none of your clothes bring you joy, stay calm and try to tackle this beast in stages.

For experimentation—Rent the Runway

I love Rent the Runway. Every time I use it, I feel fancy. People generally know it for renting special occasion dresses. But these days, they have all sorts of clothes and accessories and an “Unlimited” subscription that’s kind of like the Netflix DVD service of clothes. For $139 a month, you can keep 3 pieces for as long as you like, or rotate any of them out of your closet. Shipping and dry cleaning are included.

A few of my favorite rentals

Tips:

  • Beyond special occasions, you can use it for things like job interviews or presentation days.
  • The easiest things to rent are statement jewelry and bags. You don’t have to worry about fit, and you can enjoy wearing them every day for a while.
  • Coats and jackets are great to rent, as seasons and trends change. Plus you can wear those daily too.
  • Blazers and silk shirts are a good use case too. You can experiment with different colors, styles, brands, and prints, without investing in something forever or worrying about cleaning.
  • Figure out your sizing in advance for brands you like. Spend a day at the mall trying on high-end brands you wouldn’t normally buy, and noting your size. After that, you can rent things anytime from RTR without having to fret about sizing.
  • Once I found new-to-me brands I liked, like Equipment, I looked them up at Nordstrom Rack. When you’re ready to invest in something to keep, see if you can find an affordable equivalent there.

Pros:

  • It’s fun and easy, and the best way I’ve found to experiment with styles and brands you’re curious about. Having something special to wear really did boost my confidence sometimes on hard days.
  • Rent the Runway has the best selection of high-end brands, compared with competitors like Le Tote.

Cons:

  • Shipping times are slow. There’s about a week of turnaround time between sending something back and receiving a new item.
  • You have to be flexible, since availability changes often. If you have a specific piece in mind, you might have to wait a couple cycles to snag it in your size.
  • It’s expensive. I used Unlimited for a few months. After I ended my subscription, I had some lovely photos and experiences to show for the expense, but my closet was pretty empty. Ultimately, I decided to shift my clothing budget toward things I could keep.

For curation and fit—Stitch Fix

I gave Stitch Fix two tries and lots of feedback, but I didn’t end up keeping anything they sent.

Pros:

  • It was nice to receive a curated selection of just a few things.
  • Everything they sent fit.

Cons

  • You’ll pay full price for everything.
  • I didn’t like the styles very much. I think they were too trendy for me.

Tips:

  • This service might be for you if you’re open to trying new things, don’t mind paying full price, and don’t like to choose for yourself.

For curation and flexibility—Trunk Club

I gave Trunk Club two tries. The first time, I spent a lot of time documenting my existing wardrobe and explaining what I was looking for. Then I received an enormous box of things that did not fit or seem remotely relevant.

A few months later, I gave it a second try and really loved the experience. This time I was able to remove things I didn’t like from my trunk before they shipped. My new stylist helped me find just what I needed, within my price range. I ended up with a few things I probably wouldn’t have found on my own, and it took less time than shopping for myself.

The trunk I liked from Trunk Club

Tips:

  • Trunk Club is owned by Nordstrom, so that’s the catalog your stylist is working with.
  • This is a helpful service if you don’t have time to shop and are willing to pay full prices. It’s especially great if you’re matched with a stylist you like and plan to reach out to them with regular requests. Then they can get to know your preferences over time.
  • This could be really helpful if you’re going through a big change, like a new job or a pregnancy.
  • If you do have time and don’t want to pay full price, this service probably isn’t for you.

For discounted designer brands—Tradesy

Tradesy is a great place to shop for high-end bags, shoes, and clothes at secondhand prices. I got a perfect pair of Stuart Weitzman heels for $45, and I’ll probably keep them forever for special occasions. They were just what I needed, and the purchase process was really easy.

Brands I love

For your SF Uniform—Everlane

If you need basics, Everlane is the one-stop shop for a super cool, streamlined, San Francisco uniform. Since they sell directly to consumers online, it usually costs less than similar-quality items in a department store. Plus, they’re transparent about how and where their clothing is made, and how it’s priced.

Tips:

  • Good for cashmere sweaters, silk shirts, and jackets
  • Their shoes run narrow
Everlane

For sustainability + French girl style—Amour Vert

If you like Anthropologie, but you’re looking for a brand with sustainable practices, Amour Vert might just be it. All of their clothes are made in the US, with non-toxic dyes, sustainable fabrics, and a zero-waste philosophy.

Tips:

  • If you’re in the Bay Area, look out for sample sales.
  • Sometimes you can find Amour Vert on sale at Nordstrom, Revolve, or ShopStyle.
Amour Vert

For beautiful bags—Matt & Nat

After a long search, I found my ideal laptop bag from this vegan Canadian brand. The shapes and colors are so lovely, and since they’re not leather, the prices are lower than you might expect.

Matt & Nat

Maintenance Mode

After a thorough closet purge, many experiments, and a few investments, my wardrobe is now in maintenance mode. I keep my closet pretty organized, so I can easily spot things that are falling out of rotation.

When something doesn’t fit or isn’t working, I’ll usually take it to Crossroads and get a credit. Recently I brought in 3 things that no longer fit and used the credit to get two new things that did. One was a cashmere sweater (!). It feels like getting FREE CLOTHES.

What I learned

Here’s the cheat sheet I wish I’d had a few years ago.

Things that are great to rent:

  • Statement jewelry
  • Fancy bags
  • Occasion dresses
  • Trends that are fun but will probably go out of style

Things that are great to buy secondhand:

  • Jeans. These are sturdy, so it’s easy to find used pairs in great condition. Jeans are often pretty expensive at full price, so the secondhand search is worth it.
  • Coats & Jackets. See above. Classic peacoats and trenches never go out of style, so secondhand is a great way to go.
  • Designer dress shoes. Usually worn twice—once by you and once by the previous owner. Why pay full price?

Things that are great to buy on sale:

  • Silk shirts and cashmere sweaters. They’re delicate, so a little harder to find secondhand in great condition. But they also never go out of style, so there’s no reason to pay full price.

Just go for it:

  • Everyday shoes. If you can find shoes that are comfortable and also make you feel fancy, GET MULTIPLES.

If your clothing budget is on hold:

Burt’s Bees satin lip color

Things I haven’t tried, but am still curious about

Have you tried them? Do tell.


Want to dig deeper into everyday choices? Sign up for letters or get coaching.