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Looking Good When You’re Feeling Bad: Chemo Headwear & Outfit Ideas

My Sixth Chemotherapy Treatment: No More Chemo & Great News!
Christmas Sweater Vest to Halter Top Refashion

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I’m sitting in the infusion room getting what will hopefully be my 6th and final chemo treatment as I write this. So Meta, right?

One of my biggest struggles since undergoing Chemotherapy for Ovarian Cancer has been seeing myself get weaker, increasingly hairless, and looking sickly all the time.

When I wake up and look in the mirror, the person I see doesn’t look like me.

refashionista in infusion room
Funtimez at the infusion center!

Of course, the side effects from treatment for this disease are dreadful (and thankfully lessened with myriad medications).

But feeling the loss of my identity as an at least kind of cute girl with a unique style just adds insult to injury. And man…my body feels injured enough already. Why does my self-esteem have to take a hit as well?

Finally, after weeks of self-pity, I had a thought that changed how I felt about my appearance as I progressed through cancer treatment.

If I can’t feel pretty right now, I can at least feel fabulous.

Read that again, please.

Chemo Headwear: Bald vs. Scarves vs. Hats vs. Wigs…Which is best?

Bald is Beautiful!

Ten years ago I shaved my head for a charity that raises funds for childhood cancer research, and I really liked how I looked bald. I ended up shaving the growing stubble a couple of times before growing my hair out again. Some may remember I was bald when I first started this blog!

A photographer friend of mine shot a few awesome pics of my ‘do (or lackthereof).

refashionista bald
Me from 10 years ago was dramatic, no?

Back to the present!

When my hair started falling out in clumps after my first chemo treatment, I buzzed my hair waaaaay down.

After putting on makeup, accessories, and a bold bright outfit, I began to like my shaved head again this go-round, even if it wasn’t my choice.

refashionista buzz cut chemo
Accessories matter.

I mean, sure…my skin wasn’t looking its best, and I looked and felt pretty tired, but I felt confident with my new look, unplanned though it was, and a few friends even told me I looked like a badass.

refashionista with shaved head in bright outfit
$1 thrifted top, $1 thrifted scrub pants, ModCloth boots, and thrifted vintage accessories.

If you’re rocking the bald look during your chemo treatment, I recommend taking the same bold, bright, and/or dramatic approach to your outfits. Why not break out those huge earrings you never wear & a chunky necklace?

Scarves are Smashing…and VERY affordable!

I own approximately 100 scarves, friends. I inherited most of these from my grandmother, and have thrifted most of the rest. They rarely cost more than $1.

As more and more of my head stubble started falling out, my scalp was patchy-looking and very tender.

This meant I couldn’t just shave my buzz cut down to the scalp (It would’ve been too painful). But I still wanted to be comfortable and cute!

My scarf collection came to the rescue!

refashionista in printed headscarf
Pattern clashing is fun!

The soft fabric of my scarves was cool and comfortable, even on warm days. My newly-sensitive scalp didn’t hurt at all while I wore them. Plus, they kept the sun off my head.

refashionista in brightly patterned vintage dress and headscarf
When I’m feeling blah, I like to dress up in my favorite vintage frocks!

For warm-to-hot weather, headscarves are a great option!

refashionista in headscarf with large vintage necklace
Big vintage necklaces don’t hurt either!

I recommend pairing your bright and pretty headscarves with equally bold and stylish vintage dresses!

refashionista in green '70s vintage dress, red vintage necklace, and vintage headscarf
Don’t be afraid to be bold!

There are so many fun pairings your can come up with!

I felt super put-together in my scarf & dress combos and they really made me feel more confident and happy with my appearance.

I pretended I was an eccentric gallery owner as I walked down the street in my artfully-curated ensembles.

Hats…because that bald noggin gets ccccccold!

I loved my scarves, but as the seasons changed and the weather got cooler, they just didn’t do enough to keep my head warm. :/

I opted for hat styles that I already enjoyed wearing, rather than cloches or more structured hats (which I don’t think good on me). It’s been really important for me to feel like I’m making style choices I would go for even if I weren’t sick.

Berets have been my favorite hat style during chemo treatment!

jillian in white sweater and matching beret
Mon dieu! So fashionable!

I only owned a couple of these pre-treatment, so I went ahead and ordered a big multipack of berets from Amazon.

Now I have a hat for just about any outfit I could think of, including my refashioned deconstructed sweater in the above pic, and this dress I gave puff sleeves & decorative stitching!

refashionista in yellow beret and dress with matching decorative stitching
I added that yellow stitch just to match my yellow hat!
Looking Good When You're Feeling Bad: Chemo Headwear & Outfit Ideas 1
Wearing a vintage beret that used to be my grandmother’s with a $1 thrifted skirt and $1 thrifted sweater!

I’ve also been enjoying slouchy knit hats like this one, especially when I’m just hanging out at home in sweats.

refashionista in slouchy hat and sunglasses
The height of coziness.

This lightweight knit slouchy hat comes in lots of colors, too!

Wigs: The Good, the Bad, & the Expensive

When I met with a nurse at my oncology center before I started chemotherapy, she advised me to go ahead and buy a wig before my hair fell out if I wanted to wear one.

If I wanted to wear one? I’m a former theatre major! Of course I wanted to wear one!

Fast forward to now:

Looking Good When You're Feeling Bad: Chemo Headwear & Outfit Ideas 2
I may have a problem.

I am now the owner of several wigs.

At first, I thought I would like longer wigs best.

Looking Good When You're Feeling Bad: Chemo Headwear & Outfit Ideas 3
Tabu by Ellen Wille and Wavy by Hairdo (heavily modified)

My bio hair is naturally coarse and very thick. It takes forever to style when it’s long and I have to get regular keratin treatments to keep it looking presentable.

But wigs have none of those problems! Since I only bought wigs with synthetic fibers, the styles are basically baked into place, so there’s not much styling required.

jillian in rachel by Jon Renau wig
Rachel by Jon Renau

While I used to spend upwards of 40 minutes styling my hair, now I can look coiffed in five!

brian and Jillian in Code Mono by Ellen Wille wig
Code Mono by Ellen Wille, but I named her Amy!

Unfortunately, most of my time wearing these was spent swiping polyester hair off my face. They also tangle in the back very easily.

They don’t last very long either. You might get three months of wear out of a longer wig if you wear it regularly. That’s not many wears for the steep price!

Why I think Short Wigs are better, especially for chemo patients:

The pixie wig below absolutely ROCKED MY WORLD. I LOVE her.

refashionista in risk by ellen wille wig
Risk by Ellen Wille (but I named her Liza)! I have her in three colors!

I’ve had short hair before, so I feel very comfortable in short hairstyles.

In my opinion short wigs look more natural, are way more comfortable (not so much hair in your face), and last MUCH longer than longer wig styles, as the fibers don’t rub against your clothing and get all tangled and worn out.

Jillian in Tori by Rene of Paris Wig
Tori by Rene of Paris

Also, It’s much easier to navigate wearing a mask with short wigs. Especially when you’re like me and are probably wearing earrings and sunglasses too (so many cranial accessories!).

jillian in victoria by jon reanau wig
Victoria by Jon Renau

The biggest drawback of wigs is that they are expensive. They can also be scratchy and uncomfortable, even with a wig cap. You really have to try them on to tell if you’ll like them. I discovered I prefer to only wear them occasionally to help them last longer and because other options are much more comfortable.

Wigs with hand-tied monofilament caps cost around $400 and up (unless you find a good sale), but they look more natural as the fibers part and move like they would if they were growing out of your scalp.

You can find a decent open weft cap wig (with a fixed part) for $80-150. They won’t move the same way hand-tied wigs do, and you can’t control the part, but for some styles that’s really not much of an issue.

jillian in wavy by hairdo wig
This wig (Wavy, by Hairdo) has an open weft cap and no part. I also had my stylist thin it out and trim the bangs for me.

I bought the wigs you see here from and (less pricey option). They both have excellent return policies, so you can try on a wig and then return it if you don’t like it (which I’ve done several times).

They’re not paying me for this post, and I don’t get a commission for any wig sales referred by this post, so you can trust me. 😉

But what’s my favorite headwear while I’m going through chemotherapy? Bald (aka no headwear)? Scarf? Hat? Or Wig?

The answer is I have no answer. I feel like each one has had its place in my cancer journey.

  • Going bald can feel empowering! It feels great to walk out into the world with no hair to hide behind and just let your unique beauty, personality, and style shine. Just make sure to wear sunscreen if you’re outside or your scalp will burn!
  • Scarves are effortlessly classy & bohemian. They can elevate any look while still keeping my sensitive scalp happy.
  • Hats are like a cozy pair of sweatpants…great for warmth (duh), but can also give an outfit an artsy sophisticated look.
  • If hats are like sweatpants, Wigs are like fun party dresses or a nice pair of high heels.

They’re not the most comfortable option, but they’re fun! You can try a totally different look (I assign a different name and personality to each of my wigs). Or you can get at least somewhat close to how your hair looked pre-treatment (which can be comforting).

Another thing to keep in mind is that wigs are hot, and not in that early aughts Paris Hilton kinda way. Wigs with open weft caps let air flow through better those that are of the hand-tied monofilament variety. On a hot summer day, you might want to opt for a pretty sun hat, a scarf, or your bald beautiful noggin!

I don’t recommend going on a wig buying spree while laying in bed in a chemo brain fog haze (like I did), but at least one wig might be fun to wear on occasion, even if you don’t wear it every day (I don’t.).

jillian in headscarf in her sewing studio
Rocking the headscarf in my sewing studio!

Coping with cancer treatment is hard. You are under no obligation whatsoever to get dolled up if you don’t feel like it.

Strength is beautiful, and whether you’re going through chemo or any other rough patch in your life, keep in mind that’s it’s more than okay to just hang out sans makeup in ratty pajamas (what I do most of the time).

jillian in thrifted outfit and beret
Keeping it casual in a $1 thrifted dress, $1 thrifted vintage sweater vest, and my cozy beret!

But sometimes, on good days, I go to my closet and pick out something special that makes that day just a little better.


Chemo Headwear & Outfit Ideas

Do you have experience with hair loss? Which look (or is there another not mentioned here?) do you prefer for your own personal style?

Post it in the comments!

My Sixth Chemotherapy Treatment: No More Chemo & Great News!
Christmas Sweater Vest to Halter Top Refashion