Beatles Abbey Road t-shirt // pastel Chevron shorts // sushi print novelty socks // Doc Martens // purple lenses glasses used as hair accessory // Wet ‘n Wild pastel paint palette eyeshadow in orange 

I love the contrast between the darkness/masculine elements of the Beatles t-shirt (which is a new addition to my wardrobe, & I wore it for the first time a week ago at my Busch Gardens Tampa audition!) & the feminine pastel of this shorts (which I got in the children’s section!). The same contrast also occurs between the edginess of the Doc Martens & the playfulness of the purple fake glasses (which as they are unreasonably big for my face, I decided they looked quite nice as a hair accessory). And the sushi socks are just there to be funky. I love contrast in an outfit, & I love funkiness more than pretty much anything, so when you take funky things THAT contrast, it takes it to a whole new level of Funkytown.

Previous Outfits of the Day // April 20, 2017

Cool outfits I discovered in my photo archive.

Leopards + Giraffes

George white dress shirt / grey & black leopard print sleeveless shirt / ponytail / pink round earrings / white giraffe earrings

I wanted to wear something that looked cool & casual, but also had fun wildlife safari vibes. The outfit was monotone in blacks, greys, & whites, with a surprise touch of pink.

Special Effects Red Ombre Hair

Batman Shirt & Red Hair

Special Effects red ombre curls / grey & yellow Batman shirt

Floral Sweater & Red Hair

Special Effects red ombre curls / floral + black sweater

These photos are from a time I dip-dyed the ends of my hair red with Special Effects Nuclear Red hair dye. It was winter, so I am also seen wearing an awesome cozy floral sweater & a Batman t-shirt.


Black lacy sleeveless shirt & braid 2

black lace-edged sleeveless shirt / ponytail braid / “HAPPY” earrings / tiny cupcake earrings

Black lacy sleeveless shirt & braid 3

I’m pretty sure I wore this one to go to the local ice cream parlor & to do some shopping. It had cool casual vibes to it, & anything is better with tiny cupcake earrings. Also, I love the round silver earrings with “HAPPY” embossed in them.

Black lacy sleeveless shirt & braid


pink v-neck t-shirt / floral print skater skirt / pink, white, & blue polka dot socks from Michaels / clear glitter jelly shoes / moonstone heart charm necklace (moonstone charm from Etsy) / sparky black hair bow / old watch / bright pink lipsticks / cherry earrings / diamond earrings

I think this outfit had the perfect mixture of classic style (a skirt, the old leather watch, hair bow) & cool funky pattern & color combinations (polka dots + floral, blue, pink). I love my moonstone necklace, & the jelly shoes are an awesome thing to add to pretty much any outfit.

 Galaxy EyelidsGalaxy Eyelids

Galaxy Eyelids

Galaxy Eyelids

I made layers of various shades of purple & blue eye shadow, then drew the dots for stars with silver glitter eyeliner that I bought at Claire’s.

Galaxy Eyelids


Galaxy Outfit

George white dress shirt / galaxy leggings / combat boots from Walmart / blue nail polish / galaxy eyelids / ponytail / “HAPPY” earrings

Galaxy Outfit

This is the outfit I wore with the above “Galaxy Eyelids”. I LOL now seeing my old pair of combat boots, which I had before I bought the Doc Martens I have now. Gotta love all things galaxy print though.

Pineapple & Ponytail

Pineapple Shirt & Ponytail

pineapple print t-shirt / ponytail

My hair is always cool & curly.

Red Flannel

Red Flannel Shirt & a Bun

red flannel shirt / bun / everyday makeup

My favorite red flannel shirt + a sleek bun.

Legwarmers & Floral Shirt

Legwarmers & Floral Shirt

floral button up collared shirt from thrift store / shorts / grey legwarmers / black & white Converse-style tennis shoes / old watch with leather strap / tiny cupcake earrings / winged eyeliner / silver round earrings

Legwarmers & Floral Shirt

Legwarmers & Floral Shirt

Thrift store finds + funky 80’s style legwarmers = DOUBLE WIN.

Recent Outfits of the Day : March 29, 2017

Black & White Plaid Shirt

Ashlee Craft wearing a black & white plaid shirt & sparkly headband

Black & White Plaid shirt from Joe Boxer / sparkly black headband / round glitter earrings / pale purple round earrings / minor makeup / ponytail

The first time I wore this black & white plaid shirt that I bought at K-Mart, I fell in love with how it fit me & how nice it looked on me. It was very comfortable, & I liked how the whole outfit looked with my hair pulled back & this yellow wall at the theatre.

My Drama Face

Ashlee Craft wearing a blue sweater, green eyeshadow, theatre makeup, a dress shirt, & ponytail

Cream dress shirt from Devon & Jones / blue sweater from Target / coral lipstick / dramatic theatre makeup (for my role as Puck in Ken Ludwig’s Shakespeare in Hollywood) / ponytail

Because I was wearing such exaggerated, dramatic makeup, I couldn’t help but make a humorously dramatic face as I took this selfie. I like how the bright blue of the sweater looks with the red of the lipstick, & even a less dramatic green eye shadow could look nice in a different version of this outfit. The cream dress shirt also matched it nicely.

Ruby Noir

Ashlee Craft with Schwarzkopf Ruby Noir 1.8 hair

Glow-in-the-dark Batman t-shirt / hair colored the day prior with Schwarzkopf Ruby Noir 1.8 hair dye

These photos were taken the day after I colored my hair with the Schwarzkopf Ruby Noir 1.8 dye that I bought. It’s my favorite hair color that I’ve used, & using it was also the first time I’ve applied hair dye to all of my hair & not just the ends. I’m squinting & making weird faces because the sun was in my eyes. I colored my hair probably almost two months ago & it still is visible in my hair, which makes me happy. It didn’t dry out my hair, & I’m really pleased with its quality.

Ashlee Craft with Schwarzkopf Ruby Noir 1.8 hair

Ashlee Craft with Schwarzkopf Ruby Noir 1.8 hair

Ashlee Craft with Schwarzkopf Ruby Noir 1.8 hair


Doc Martens / blue jeans / red plaid shirt / white camisole / multicolored headband / blue crystal earrings

I liked the rustic workman look of this outfit. I used to dress like this a lot when I was in my Bob Dylan phase. I still like how it looks, & adding Doc Martens to this type of ensemble just makes it even more epic & badass. For a funky, unexpected touch, I wore a great multi-colored headband that technically belongs to my sister,

Ashlee Craft wearing jeans, boots, a red plaid shirt, & a multicolored headband

Kawaii Eggs

Ashlee Craft wearing a white t-shirt, cute kawaii egg earrings, & multicolored headband

white t-shirt with pocket / cute kawaii egg earrings from Claire’s, multicolored headband / ponytail

I wore this outfit when I went shopping & then to a carnival. The shirt kept me cooler in the sun than a darker one would have, the headband & ponytail kept my hair out of my eyes, & the egg earrings added a touch of funkiness.

More Egg Earrings

Ashlee Craft wearing a pink t-shirt & cute kawaii egg earrings

Pink t-shirt from Target / cute kawaii egg earrings from Claire’s / minimal makeup

An outfit involving the same adorable egg earrings from the previous photo, along with one of my favorite shirts. A nice simple everyday outfit.

Yellow + Stripes

Ashlee Craft wearing black heeled jelly shoes, sloth socks, striped shorts, & a yellow shirt

Yellow t-shirt from Target / gray & white striped shorts from Target / cute rainbow monsters with wings earrings from Claire’s / blue star stud earrings from Claire’s / black heeled jelly shoes / sloth socks from Target

I really liked how this whole outfit came out. It had lots of colorful, bold elements, like stripes, the bright yellow, & black shoes, as well as lots of whimsical, funky elements, like the sloth socks, the fact that the shoes are jelly shoes, & the rainbow monster earrings. These photos also show how nicely my red hair color faded & still remains visible even now.

Ashlee Craft wearing black heeled jelly shoes, sloth socks, striped shorts, & a yellow shirt

Previous Outfits of the Day, #1 (Including Ombre Rainbow Eyebrows & Red Ombre Hair!)

Special Effects Nuclear Red Ombre & Debut of Rainbow Eyebrows!

Special Effects Ombre #2

red ombre hair / blue & teal rainbow eyebrows / blue & gray striped shirt customized by me by adding the gray flower I crocheted & embellished with beads

Ombre Hair with Nuclear Red Ombre & Teal & Purple Rainbow Eyebrows

A few weeks ago, I decided I wanted to lighten the ends of my hair so I could dye them a bright color. I watched a YouTube video where someone used a blonde Garnier hair dye to lighten their dark brown hair. I decided to try Nutrisse Nourishing Color Crème in 93 Light Golden Blonde, & as I’d had good luck with the high-lift red I used last summer for my red & brown ombre, so I assumed this one would work just as great. Unfortunately, my hair is quite impervious to coloring, & the dye had little effect. Luckily though, it added a few lighter brown highlights, as well as damaging my hair a little bit more to allow the hair dye to soak in more.

Originally, I was going to do a rose gold ombre, but as my hair didn’t get light enough for that, I decided to go for my Nuclear Red Special Effects hair dye. The Special Effects dye definitely works better on my hair than Manic Panic, although it didn’t show up very well with my natural hair color. I love Special Effects, btw. I put the Special Effects dye in my hair, & let it sit under a shower cap for 30+ minutes. When I rinsed it out, I was pleasantly surprised by the bright color! It was just what I had hoped for with the Nuclear Red. The dye faded out over a little more than a week, & now is a subtle red color, which is also pretty. Soon, I hope to go to the salon & get the ends of my hair bleached for real, so that I can dye it whatever color I want.

Purple & Blue Colorful Eyebrows

Also, my sister taught me how to do rainbow eyebrows, because I’d seen plenty of photos online of them, & my sister has done them quite a few times on herself. Thanks to my e.l.f angled brush & some bright-coloured shadows, I soon achieved a teal & purple ombre effect, which I was happy with. I definitely want to try more things with the rainbow eyebrow trend, because it’s one more way to look cool + colorful.

Blue Bow & Stripes

Blue Hair Bow and Striped Bon Worth Blouse

Red and blue striped blouse from Bon Worth / cherry earrings / diamond earrings / blue hair bow headband

A cool picture I took with the sky as my background. The sky ended up looking cool & washed-out, which goes along well with the slightly-wistful expression on my face. I matched the colors of this blouse with my red earrings & blue headband.

Gold & Winged Liner

Gold & Winged Liner

gold short-sleeved blouse from my grandmother / winged eyeliner over gold glitter eyeshadow / sparkle “celebration” earrings. worn during winter/spring.

I had been wanting to create an outfit with this awesome glitter blouse for a long time, but the last time I’d tried it on, a few years ago, & the fabric was very scratchy. Thankfully, I discovered camisoles, & wearing one under this blouse made it comfortable to wear. I decided to pair it with the Elizabeth Taylor elegance of winged liner, & one of my favorite pairs of sparkly earrings, which I have just dubbed my “celebration” earrings. For added measure, I added gold facial glitter to my eyelids, because if you’re going to wear a sparkle outfit, you might as well go all out.

Leopard Print & Dress Shirt

Leopard Print & Dress Shirt

unbuttoned white dress shirt / gray & black sleeveless leopard-print shirt / round neon pink earrings / white plastic giraffe earrings / ponytail

I felt like wearing my leopard-print sleeveless shirt, because #funkypatterns, but my arms were cold so I decided to put my favorite white dress shirt over it. To add to the ensemble, as well as tie in with the color of the dress shirt & continue the safari theme, I added white giraffe earrings. For a small splash of color, I wore my favorite neon pink earrings in my second ear piercings.

Classic & Simple
Simple & Classic

multi-cabana stripe dress shirt by Devon & Jones / black ballet flats / black capri tights

I went through a big fashion phase last year where I pretty much just wore dress shirts, even when I wasn’t at work. I don’t wear them as often now, mostly because there are other things I like better (& are probably a little more comfortable). Dress shirts provide a clean, classy look, & they can be made more casual by both rolling up the sleeves, & by pairing them with less formal accessories, like the capri tights. Simple & Classic #2

With glitter & happiness,


Favorite Fashion Trends, June 2016

1. Bold Blue Eyeliner

Blue Eyeliner


When I watched Wes Anderson’s Moonrise Kingdom for the first time, I was immediately struck by how awesome the funky-vintage blue eye makeup that Suzy wears is. It’s a bold look which manages to look both modern & vintage at the same time. When I saw the ad for the Aqua XL teal eyeliner (featured above), I started thinking about how great the Moonrise-Kingdom type look would be if you used a wide teal eye pencil. Then, I read this great article about blue eyeliner looks from Refinery29, & it reinstated my desire to try something like this. I haven’t gotten around to purchasing a nice, saturated blue eyeliner or shadow yet, but I’m thinking about maybe trying the Color Tattoo eyeshadow in Tenacious Teal, because I own some gold Color Tattoo shadow & I’m very pleased with it.

2. Jumpsuits & Rompers

A Few of my Favorite Jumpsuits


When jumpsuits & rompers first started picking up in popularity, I found myself slightly intrigued with them. I would occasionally search Amazon for them, & I thought they were cool because ones with shorts bottoms would be like wearing a really cool, matching pair of shorts & a shirt in the summer, & wearing a pants-version could look like a hip, vintage 70’s type of disco look. Admittedly, I’m not totally crazy about the cuts of a lot of rompers I see, but I really love the above rompers/jumpsuits. Some features that I find appealing in jumpsuits are monochromatic colors, button-down-type shirt collars, interesting but relatively simple patterns, & glitter.

3. Enamel Pins

Groovy Enamel Pins
Enamel pins are one of my new favorite things. I am seriously so obsessed with them. All I want to do is look for them at local thrift stores & make my own enamel lapel pins (more should be announced about this soon!). I just bought my first enamel pin, this really really awesome one featuring sloths holding a surfboard while riding a bike. I can’t wait for it to arrive! Why do I love pins so much? The short answer is : they are another awesome avenue to express myself.
A few more reasons?
  • I love the DIY, punk aesthetic of pins
  • They allow you to say something about yourself + your opinions (to help you connect with like-minded people)
  • They are reasonably cheap, fun, & easy to collect (like stamps, another favorite collectible of mine.)
  • They are a fun, colorful way to add to any outfit

4. Watermelon Print Summer Things

Watermelon Themed Summer Clothes


I love watermelon print things because watermelons are pretty much the epitome of summer, & I love summer. Watermelons are such a bright, fun, funky print. It would be awesome to wear an outfit entirely made of watermelon themed items, & if you owned a lot of clothes with this print, you could keep a little piece of summer with you all year round, & a nice splash of color. Out of the items pictured above, I especially love both of the watermelon print shirts!
What are your favorite fashions right now? Let me know on Twitter!

Recent Outfits of the Day // February 12, 2016

Glitter + Dress

Recent Outfits of the Day // February 12, 2016
dress by Simply Couture / black knee-length tights / glitter jelly shoes / coral lipstick / pink earrings + frog emoji earrings / gold glitter eye shadow / gold interlocking circles cuff bracelet

Recent Outfits of the Day // February 12, 2016

Let me just say how much I LOVE this dress. I bought it on zulily (which is another thing I LOVE, because I can get awesome clothes for a great price) & every time I wear it, I get so many compliments. I love it because of the unique pattern – polka dots & random artistic circles – & the interesting asymmetric cut. It’s definitely my favorite dress at the moment. I also am in love with the color combination of green & pink, which I utilized in the earrings that I’m wearing. The frog face emoji ones are especially great! & as always, everything is made better by the addition of sparkly jelly shoes.

Badass Negotiations

Recent Outfits of the Day // February 12, 2016

jean jacket from Bealls Outlet / yellow sleeveless shirt from Just Be… / black skinny pants by Be Girl / combat boots / diamond earrings / yellow triangle earrings from Claire’s / minimal makeup

Recent Outfits of the Day // February 12, 2016

For this outfit, I wanted it to look badass. So I did one of my favorite combinations of a sleeveless shirt & a jean jacket, which to me, just looks badass for some reason. I would have used a leather jacket, but because I don’t currently own one, I used my jean jacket instead. My love of utilizing skinny jeans to make an outfit a little edgier – an inspiration which I attribute to Bob Dylan – was also something I drew on here, along with combat boots, which instantly make any outfit look that much more badass. I think this was the first time I ever wore these great earrings from Claire’s, even though I had them for a long time, but I loved them. I practiced making a mildly unamused expression to top off the look.

Jumping For Joy

Recent Outfits of the Day // February 12, 2016

red blouse from thrift store / George white dress shirt / striped tights / combat boots

This was an outtake from the #radicalselflovejanuary photo challenge by Gala Darling. The photo I ended up using was this one, but in this photo you can see the whole outfit better. Earlier in the day, I paired up my red blouse with my “mime tights”, because they look great with red. I put on my combat boots, & because the weather was a little chilly, I put my white dress shirt on over my blouse like a jacket. It was the perfect fun & whimsical outfit for a fun & whimsical photo shoot.

Dark Plum Manicure

Recent Outfits of the Day // February 12, 2016

I had been wanting to paint my nails for a long time in order to go along with the new persona I was working on developing, but because I was busy (& because nail polish takes FOREVER to dry completely on my nails), I hadn’t gotten a chance to. When I finally did, I selected Revlon #490, Urban. It looked like a very deep royal blue when it was in the bottle, but when I put it on, it was more of a very deep, rich plum purple. I loved it. It also lasted for 10 days on my nails before I had to removed it, despite having a job in which I frequently hit my nails on things, so I was impressed.

Pastel Zig-Zags

Recent Outfits of the Day // February 12, 2016

yellow sleeveless shirt by Just Be… / jean jacket from Bealls Outlet / pastel zig-zag skirt from Bon Worth / Revlon nail polish in shade 490 – Urban / gold glitter eye shadow /  combat boots (not shown)

Recent Outfits of the Day // February 12, 2016

I bought this really great skirt at Bon Worth a while ago, but I hadn’t got around to wearing it yet, mostly because I didn’t really know what to pair it with. I decided that wearing a yellow shirt would match the pastel pink & blue hues of the skirt well, so that was what I ended up wearing. I was going to go shopping in the evening & the weather was pretty cold, so I added a jean jacket & my combat boots. I was thinking about wearing my sparkly jelly shoes with this, but I thought it might be too much & wanted the focus to be on my skirt & not my shoes. I really liked this outfit, & I really liked the way my hair looked in the second photo. I’m loving the new way I’m parting my hair!

How to Dress Like Bob Dylan, Part II

Working Bob Dylan’s electric style into your wardrobe.

Disclosure: This post may contain affiliate links to products that I recommend. When you click on an affiliate link to a product on an external website, I will receive compensation if you buy something. Thank you for your support.

The Effortlessly Cool Dylan


At the Newport Folk Festival in 1965, Bob Dylan did something bold : broke away from his folk roots & played his first-ever rock set live on stage. This was radical, as many had hailed him as the definitive symbol of folk music, & all of a sudden, he was transitioning away from what he’d always been. Reinventing himself. & that, I believe, is one of the most inspiring things about Bob Dylan : the way he confidently became something entirely different & didn’t give a damn what folk purists thought of his decision. He did what he wanted to do & what he thought was cool.

This was the beginning of Dylan’s “Electric Phase”, which spanned from 1965 all the way until his motorcycle accident in 1966. This is perhaps my favorite of his fashion eras, because this was when Dylan wore a uniform of suits, skinny pants, Chelsea Boots, untamed curls, & Ray Ban Wayfarers. Dylan, in this phase, was undeniably cool looking. Undeniably sleek, with a splash of rebellion & a lot of class.



The Electric Bob Dylan



1. Black or White Dress Shirts. Any neutral colored dress shirt will work. Dylan wore dress shirts extensively during his electric phase, mostly under blazers & with skinny pants. I love adding dress shirts to outfits when I want to make them look sleek + refined in some way, & I find them very comfortable. Wearing a dress shirt is a great place to start & will add a nice, classy touch to your electric ensemble.

2. Polka Dotted Button Down Shirts. In some photos from the mid-60’s, Dylan wore a black & white polka dot shirt, similar to the one on the left. The larger the polka dots, the more retro & therefore authentic it will look. You could also wear a white & black polka dotted shirt like the one on the left, because it stills captures the sleek vibes this outfit radiates.

3. Skinny Trousers / Skinny Jeans. Black or other dark-colored skinny jeans or pants will work excellent for this outfit. Skinny pants look SUPER GREAT with heeled boots, as pictured below, & plus, they’re highly versatile & can be worked into pretty much any outfit, so if you don’t already have a pair, you should think about getting some. A good pair of skinny pants will look casual when you need them to, but can be dressed up for more formal occasions. As mentioned in Part I, you could also wear a dressier pair of shorts like these Dickies shorts or these Style & Co twill shorts for your outfit, depending on the weather & your preferences.

4. Black Skinny Blazer. Bob Dylan in most photos from this era could be seen wearing a blazer, both on stage & off. There is a lot of great footage of his utilization of blazers in Don’t Look Back, the documentary about his 1965 tour. Blazers are another one of those go-to basics that I think everyone should work into their wardrobe, in whatever cut & color suits your personal style the best. Adding a blazer to this outfit makes it look instantly classy. It makes you look like a cool, important person, & it looks sleek as hell. As you can see, Dylan’s wardrobe during this phase consisted of a lot of great basics.

5. Chelsea Boots or Riding Boots. I love Chelsea boots because they look very, very polished & chic, but also add a more rugged touch to an outfit. They have a medium but sturdy heel, something I love to see in a shoe. Wearing heeled shoes makes you taller & therefore can add a special air of confidence & badassery to your outfit (especially if they’re shiny & leathery like these), & a solid, sturdy heel means that you can still run/jog if you feel like it, without falling over. Which is always a plus.

6. Ray Ban Wayfarers. The iconic sunglasses of Bob Dylan. Other rock stars of the time, such as Roy Orbison, also frequently wore the Wayfarers, but no one made them look as cool as Dylan did. Wayfarers are THE choice in epic & badass sunglasses. Legend has it that putting a pair on makes you instantly look ten times cooler & will help you win friends & influence people. Kidding (kind of), but seriously, Wayfarers are a timeless classic & have that rock star look to them which glams up whatever you wear them with. Obviously the actual Ray-Ban version is nice (pictured left) but you can find inexpensive knock-off ones (right) which look pretty much the same & cost under $10.

7. Leather Clutch. Any kind of leather purse in a chic design & a bold neutral color or pattern will look great with this outfit, but there is something nice about these leather clutches that just goes with the minimalist theme of this look. Because clutches are small, they won’t overpower the rest of the outfit or make you look too accessorized. A clutch in black looks sharp, but I also like the checkered one, because the pattern of it reminds me of the houndstooth jacket pictured below.

8. Houndstooth Jacket. Dylan wore a houndstooth jacket in multiple photos from 1966, like this one and this one. Houndstooth tends to look more old fashioned than some patterns, but if you wear it with the right outfit, it can look classy & modern. If you’re not feeling the retro-jacket thing, go for a houndstooth accessory, like the scarf featured above (which, I must note looks exactly like the one Dylan wears on the cover of Blonde on Blonde) or a houndstooth purse.

9. Suit Vest. Classy & sleek, & when worn without a suit jacket, classy-casual. Dylan wears a vest like this in the iconic Subterranean Homesick Blues video. Suit vests are another piece of clothing that I love the look of. Wear the vest unbuttoned over one of the aforementioned neutral colored dress shirts, & then pair it up with a pair of blue jeans & the Chelsea boots to match his outfit in the music video perfectly.
For some more inspiration, here is a video of him playing Maggie’s Farm at the Newport Folk Festival in 1965.

Read How to Dress Like Bob Dylan, Part I: Folk Phase.

Indiana Jones Halloween Costume!

Disclosure: This post may contain affiliate links to products that I recommend. When you click on an affiliate link to a product on an external website, I will receive compensation if you buy something. Thank you for your support.

Indiana Jones Halloween Costume by Ashlee Craft

Harriton khaki shirt / khaki pants by Columbia / belt from my grandmother / combat boots / whip is a strap from my sister’s purse / canvas medic bag / Indiana Jones-style fedora

Indiana Jones Halloween Costume by Ashlee Craft

I’ve been a HUGE fan of the Indiana Jones movies since I was a teenager. I’ve seen all the movies several times & even read the spin-off books, comics, & movie novelizations. BIG FAN. So, this year, I decided I was actually going to dress up as Indiana Jones for Halloween this year. Also, it was an easy costume for me to make – I already had all of these Indiana Jones-themed clothes, with the exception of the hat, which had been on my fashion wishlist for a long time. 

Indiana Jones Halloween Costume by Ashlee Craft

Indiana Jones Halloween Costume by Ashlee Craft

Cue the Indiana Jones theme song!

Here are some photos of my beloved Owl Pumpkin, #becauseOwls.

Owl Halloween Pumpkin by Ashlee Craft

Owl Halloween Pumpkin by Ashlee Craft

Owl Halloween Pumpkin by Ashlee Craft

Owl Halloween Pumpkin by Ashlee Craft

Also, here is a video of my dog wearing his Yoda Halloween costume.

How to Dress Like Bob Dylan

Disclosure: This post may contain affiliate links to products that I recommend. When you click on an affiliate link to a product on an external website, I will receive compensation if you buy something. Thank you for your support.

Bob Dylan in November 1963

Bob Dylan, 1963

When I was sixteen years old, I discovered folk music, & more specifically, Bob Dylan. I was a somewhat angry, emotional teen at the time, & felt outraged by all the wrongs in the world. I was also trying to find my creative groove, because I was learning to play guitar & I wanted to write songs, ones that weren’t cheesy sounding. I also wanted to try my hand at poetry, because I was working on being an author. I had just transitioned from being in my Beatles phase, where I obsessed over The Beatles & early 60’s pop, but had been finding happy-go-lucky melodies about holding people’s hands & other love-related themes a little too bland for my current emotions.

When I heard Blowing in the Wind, I finally found something which resonated with me. Hurt & angry & disappointed, but also strangely hopeful at the same time. Then I heard the songs Forever Young & Like a Rolling Stone. I was hooked. I knew I’d found something great, something that really spoke to me. Something angry, something passionate, something emotional that really shook me to my core & made me question who I was & how I felt about the world. I was enamored by the creativity & poetry of his lyrics, & the folksy non-conformity of Dylan as a person. I was also inspired by his style : rugged, windblown, honest, earthy; & then in his electric phase, sophisticated & sleek, & incredibly cool, in a rebellious, honest sort of way. Now, I could give a big rant about how awesome Bob Dylan’s music is, & how his work has influenced mine, but that will have to be a different post.

This article will be about how to work Bob Dylan’s signature style into your daily outfits. This is Part I, which will be about his folk phase. Part II will be about his style during his electric phase.


Bob Dylan's Folk Phase


From the time Dylan began playing in coffee houses, until approximately the Newport Folk Festival in 1965, when he “went electric”, his clothing style was simple, humble, working man’s attire. In this phase, Dylan was emulating his hero, Woody Guthrie, & therefore wanted a look which evoked the appearance of traveling hobos, migrant workers during the Great Depression, and a simple & less refined rugged honesty, qualities which were also present in his music at the time.

1. Plaid shirts. Plaid shirts in all colors will work great. Personally, I think red, blue, or gray plaid shirts capture the essence of Dylan best because they look the most rugged & add a nice masculine touch to the outfit.

2. Canvas / collared button down shirts. Earthy colors like beige or white are simple & best follow this look, but don’t be afraid to go for other colors as well. Remember, you’re doing your own take on his style, so adding your own touches, like a shirt in your favorite color, will make it even more authentic to what YOUR style is. As long as you add the unpolished, Woody Guthrie-inspired accessories like work pants and rugged boots, you will capture the vibe that you’re trying for. Although Dylan more commonly wore long sleeved button down shirts, if it’s warm out, you can always wear a short-sleeved version, or just roll the sleeves up. Personally, I love the look of rolled up sleeves. Masculine + rugged yet casual & pared-down.

3. Work Pants or Jeans. Black work pants are going to look the most like Dylan in his folk phase. I am personally a big fan of Dickies pants because they’re sturdy, quality pants, at a reasonable price. Because Dickies are actually work pants, they also add to the authenticity of the outfit. If you want to have the retro-esque “hard working” look of Dylan in this phase, wearing clothes that you could actually do labor in. Black jeans would also work, as would black shorts, especially black shorts which resemble work pants.

4. Work Boots. A good pair of work boots is a great thing to have in your clothing arsenal & can easily make any outfit a little more rough & tumble by wearing them. You could also wear another type of lace up boot if that’s more your style, or if you’re going for a very feminine take on the whole thing.

5. Brown Leather Jacket or Brown Fleece-Lined Jacket. Dylan wears a fleece-lined jacket, like the one on the right (in beige though), on the cover of his 1962 debut album, Bob DylanHe wears a different brown jacket on the cover of his 1963 album The Freewheelin’ Bob Dylanbut any brown jacket will work.

6. Newsboy Cap / Conductor Cap / Military Cap. Dylan wears a cap like this not only on the cover of his debut album, but also in many other photos from this era. The cap adds a nice little touch to the outfit, especially when paired with the style of turtleneck featured below. Very train conductor-ish.
7. Fisherman’s Turtleneck Sweater. Dylan is seen wearing this sweater in a lot of the same photos that he wears the conductor’s cap, & the combination looks very nice & cozy. I love turtlenecks in oatmeal / beige tones because they look simple, polished, & homey simultaneously, & very on-vibe with the worker aesthetic.

8. Duffel Bag Purse. A rugged looking purse, something along the lines of this, is a great purse to carry with any combination of the above outfits while still keeping with the feel of the outfit. I personally love the way the purse pictured looks because it appears sturdy, unpolished, & practical, & the combination of leather + buckles + canvas is a nice masculine touch.

If you were going to make this into a costume (or if you just want to add some real Dylan-esque vibes), add a harmonica + an harmonica holder, & an acoustic guitar. Or add those anyway, if you’re really feeling like a folksinger.

For more inspiration on this look, here is a video of Bob Dylan in 1963 playing Blowin’ in the Wind live on television.

And, a video of him playing A Hard Rain’s A-Gonna Fall in 1963. This video has a nice slideshow of photos from this era.

Read How to Dress Like Bob Dylan, Part II: The Electric Dylan.