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.

Thanksgiving Coloring Pages For Anyone!

I was feeling festive earlier, & I wanted to see a coloring page of a vegetarian tofu turkey (because tofu turkey is GOOD & I find the idea of a coloring page of one amusing), so I decided to make these coloring pages. Have fun with them! Click on the photo to print it.


Tofu Turkey & Vegetarian Thanksgiving Food

Tofu Turkey & Vegetarian Thanksgiving Food - Thanksgiving Coloring Pages // ashleecraft.comHappy Turkey

Happy Turkey - Thanksgiving Coloring Pages //

Autumn Leaves & Turkey

Autumn Leaves & Turkey - Thanksgiving Coloring Pages //

Happy Thanksgiving + Turkey

Happy Thanksgiving + Turkey - Thanksgiving Coloring Pages //


Ashlee Craft / Assemblage, Issue 6

Ashlee Craft / Assemblage Issue 6 - Cover // ashleecraft.comIssue 6 of Ashlee Craft’s life-is-a-playground art & poetry zine, Ashlee Craft / Assemblage.

very happy 4 / keep you safe 5 / even though it hurts 6 / stay 7 / rewriting the words 8 / I’ve always wanted you 9 / hurt again 10 / no more emptiness – I have arrived 12 / misty mountain fog 13 / you used to care 14 / happiness is all I want 15 / why I hurt 16 / passionate love 17 / the feel of love 18 / to endure hell 19 / re-reading 20 / strength of my own soul 21 / existing 22 / hello (I love you) 23 / best thing you’ve ever seen 24 / cashier 25 / still awake? 26 / you can’t give up now 27 / you won once (you can win again) 28 / how I felt better inside 29 / sad & happy 30 / go green with your dog 31 / a love letter to one who may never read it 32 / ramblings of the mind 33 / I don’t understand it 34 / romance is seriously so weird 35 / why it’s good you took the leap 36 / reasons being 39 / ramblings of my messy mind 41 / conflicts (i’ve felt these recently) 42 / seriously, chill out 43 / be confident in who you are 44 / a love letter : what you need to do 45 / sleep 46 / grocery 47 / not everything 48 / things that feel good to me right now 49

Publish Date // October 30, 2015
Paperback 50 pages
Genre // Magazines

Kindle Edition

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.