I have a hard time getting dressed these days.

I know I wear too much black and my clothes are rather ill-fitting and I lack a distinct sense of “THIS IS ME!” in my apparel choices. But the truth is, pre-weight loss, I was mostly trying to hide beneath my tops and jeans. I certainly wasn’t showing off in them.

I just didn’t feel good. Physically, mentally, emotionally.

Today is actually my one-year anniversary of joining Weight Watchers! And what a year it’s been. Losing 35 pounds has given me a new perspective — and though I’m still not completely comfortable strutting my stuff, I’m getting there. I mean, I’m a book nerd; I’m not someone accustomed to others’ evaluation. It feels weird.

So this post? A little out there for me. Definitely out of my comfort zone. But I figure I’m getting gutsy and ready to start investing in myself, and Stitch Fix* was calling my name.

What’s Stitch Fix?

A personal styling service that brings fashion to your doorstep. After filling out a rather extensive style profile (with all your appropriate sizing, measurements, likes/dislikes, etc.), shoppers pay $20 to have a collection of five items — dresses, skirts, tops, jeans and/or jewelry — sent directly to you.

You set the budget and share information about yourself, including a Pinterest style board (if you have one). You try everything on at home, choose what to keep and mail the rest back in a pre-paid envelope. If you keep an item, your $20 fee is applied toward your purchase. If you keep all the items, you receive a 25 percent discount on your total. Anything that ain’t workin’ for you is returned at no cost. More details are available here!

Why I’m goin’ for it

To celebrate losing four dress sizes, I decided to treat myself to a Fix and use it as an opportunity to get outside my little bubble. I scheduled my first shipment weeks ago and waited anxiously for the package to arrive, checking the tracking like a lunatic. What can I say? I’m super impatient.

In my style profile, I mentioned my changing size and desire to try wearing new things. I hate that I’m constantly in dark, drab clothing — and as I work to scale down my closet and donate items I no longer need, I’m ready to start investing in clothing I will actually wear and enjoy for years to come. Now that I’ve reached my goal weight and am determined to maintain it, the timing feels right to upgrade my clothes.

The only problem?

Money.

Like so many of us, I’ve been trained to love a “good deal” — but that $8 sweater bought on clearance looks a whole lot less inviting after a wash or two. I never paid attention to the labels or fabrics, ignoring the hems and seams coming apart rather quickly. If the item was on clearance, I bought it. Never mind that it looked flimsy and threadbare in no time.

And then who wasted their cash?

I’ll be honest — paying $50-70 for pants or a top is not typically in my comfort zone. Though Stitch Fix allows you to choose a price level for items, there are no $10 shirts. And that’s okay. I’m not rich, friends, trust me, but I’m realizing that investing in higher-quality items I truly like — versus just a bunch of cheap-o clothes I’ll tire of quickly — is going to serve me better in the long run.

If I add up all the impulse purchases I make at department stores or Target, I easily surpass the budget I would set for Stitch Fix each month. As 2014 is the year of being more accountable and conscious for my actions and my spending, I’m foregoing buying other items in favor of trying Stitch Fix. I want to get serious and sophisticated.

Mind = open.

Also, I chopped off my hair two weeks ago. It’s probably the shortest it’s ever been since I was, like, 10, so prepare to be shocked. And amazed. And maybe freaked out. It’s different, I know — and different can be scary! But I really liked it. My tresses seem slightly less insane when they’re not frizzy and long. Frizzy and short is actually much better — who knew?!

My first Fix

1. Just Black Dean Ankle Zip Skinny Jean | $78

Though I liked the fit of these, I wasn’t sure about the ankle zip detail — and I have a similar pair already. If I was in need of black skinny pants, I probably would have given them more of a fair shake! And honestly, since I wear black to work every day (and think these would have been too casual for the office), I try not to wear black in my “off-hours,” too. But they looked great with my favorite red flats and the tops included in my Fix. Including . . .

2. 41Hawthorn Brentwood Jersey Stripe Tiered Top | $68

Cute top, but too similar to items I already own. In fact, I shed the black-and-white striped top I wore to work yesterday in order to put this one on! For $68, I would have wanted something more outside my comfort zone. But the material was very soft and I really liked the tiered styling; the triangles at the bottom were flattering, I thought.

3. Collective Concepts Valencia V-Neck 3/4 Sleeve Blouse | $68

Oh, I was torn about this one — but in the end, I think the sheer quality of the fabric ultimately convinced me to wait. I hate having to constantly wear a camisole under everything. I loved the bright color, though, and thought it was really cute with heels and the black skinny jeans! I’ll have to look for something similar myself.

4. 41Hawthorn Milo Pleated Detail Skirt | $38

Cute — but too snug around the midsection. Half a cookie would have sent me into paralyzing discomfort!

And finally . . .

5. Ezra Kim Racer Back Fit & Flare Dress | $64

Winner, winner, chicken dinner! I knew I’d be keeping this one as soon as I slid it over my head. The material has a slight stretch that is sleek and polished, and my husband had to pick his jaw up off the ground when I walked out. It’s very comfortable, sophisticated and lovely.

I added my own belt at the waist, plus one of my favorite zebra-striped necklaces, and I could easily see how it would mesh with my current wardrobe while still updating my look. It’s hard to tell from that first photo, but it’s actually a very bright blue similar to the bridesmaid’s dress I wore in my sister’s wedding. Oh, like this:

The verdict

Only the blue dress, No. 5, has a permanent place in my closet now, but I absolutely loved the experience of Stitch Fix! The personalized note and style cards that accompany the pieces were so fun to read, and I felt inspired just looking through everything.

Stitch Fix was so fun, and I adored trying on clothes chosen by a stylist for me. A fellow Megan definitely nailed my interests and sizing, and I liked that the tops were in the realm of something I would normally choose while still being just a little bit different.

I already have my next Fix scheduled for February . . . and I sense an obsession a’brewing.

* Referral link. I am not being paid to write about Stitch Fix and purchased my first Fix myself, but signing up through my links will grant me a referral credit toward my next box. Thanks, friends!