Three Chic Ways To Wear a Hooded Sweatshirt



I’m not one to sacrifice comfort for fashion, and never is this more true than in FEBRUARY.  It’s cold, it’s dark, and screw red roses – I want black Calla lilies for Valentine’s Day.  (Or vibrators, haha.)   In any case, this is a long-winded explanation for my recent sweatshirt habit (which has been well-documented on my Insta account, @shanachristine).

So obviously, I turned to my dear friend, Pinterest.  We put our heads together and came up with three easy (but chic) ways to wear a hooded sweatshirt.

1.  With Tailored Wool Coats And Statement Boots



My outfit is a spin-off of this Sincerely Jules look that has been circulating around on Pinterest for quite some time.  I messed around with a few different (similar) ways to style, but in the end, this outfit formula relies on the following:

1.  Leopard Print boots (mine are flat, rather than heeled like Jules’ original pics)

2.  A tailored wool coat layered over the hoodie (color doesn’t really matter –  you just need the sophisticated lines of a wool coat to contrast with the casual hoodie – even a trench would work)

3.  Bright accessories and lipstick






Outfit Details

coat: French Connection

hoodie: Marquette, MI hoodie from Casualties

jeans: old Rag and Bone Dre – here’s the current wash, now 30% off! (Runs big – go down one size.)  Also in high-rise...oooooo…..

boots: Nine West (runs a half size big)

accessories: Gap hat, Echo tech gloves, sparkly Smartwool cable-knit socksTarte Matte Lipsurgence in fiery

On Pax: old Appaman Kids faux-leather jacket – for similar, try Appaman’s bomber jacket (hysterical), or this season’s faux-leather (now on major sale)….target leggings….Hunter First Classic Rainboot


2.  With Leggings and Layers



Leggings and sweatshirts – could there be a better pairing for a lazy weekend?  To keep this look from veering into slob territory, break up the sweatshirt and leggings with the hem of a tshirt peeking out, add a cool cross-body and a big ‘ol parka.

(This outfit was inspired by this collage vintage article.  Thanks, Nicole!)



I finished the look off with over-the-knee boots, but they weren’t a critical piece.  Plain black moto boots would work just as well.


Outfit Details

coat: old DKNY, but this one looks fabulous

hoodie: Marquette, MI hoodie from Casualties

tee: Madewell (I’m wearing size small)

leggings: Plush Moto Leggings (the XS is 50% off on Amazon) – I can’t say enough about these leggings.  Easily the most comfortable and warmest leggings I own.

boots: Stuart Weitzman Playtime Boots (sizes 9.5 and 10 are on crazy sale here or here)

bag: old Kate Spade, but any sort of quirky crossbody bag would be cute.  I’m dying over this one


3. With Flares, Leather Jacket, and a Few Stripes



This is so easy and cute – and looks surprisingly dressed up.  Since my flares, jacket and sweatshirt were all black, I broke things up a bit with a striped turtleneck (a good trick for all-black layers).  If your hooded sweatshirt is a different color, you might be able to skip the turtleneck (OR tie it all in with a black turtleneck).





Outfit Details

leather jacket: Iro (old), but I’m kinda dying over J.Crew’s version.  Pretty and tough.

hoodie: Marquette, MI hoodie from Casualties

turtleneck: JCrew Tissue Turtleneck (on sale)

flares: Citizen For Humanity Fleetwood High Rise Flares in black…the lightwash is on sale at Amazon.  Also, Current/Elliott’s Girl Crush jeans (in black) would make legs look miles and miles long

boots: old Billy Elliott but these are similar, and these embroidered Sam Edelman boots are so cool

bag: old Kate Spade c/o

sunglasses: Prada c/o Ditto


Shop The Post

For ease of shopping (if you’re so inclined), here are all of the pieces I linked to above, as well as a few additional items that caught my eye.  All perfect for wearing with sweatshirts.



Do you have your hoodies on major repeat right now?  I know I can’t be alone on this – Laura also styled up a sweatshirt earlier in the week….






      • Sadly no. The Iro. I’ve seen you wear it before – I’m slow on the uptake, but eventually I get obsessed with the things you wear – usually about a year after you debut them. (You are the definition of fashion-forward!) Stalking Ebay for a similar one. What size are you wearing?

  1. I love all of those looks and I think I can recreate them with what I already have.

    Question: why do you suppose that none of your links work for me? Ever. Which is a bummer because I really want to learn more about those leggings!

    And also, did I tell you I bought those sorel wedges you posted last week? I found last years model in the basement of my local shoe store, and they were marked down to less than 1/2 price!

  2. Love this! I’ve been trying to figure out what the hell to do with colder temps in our new location. And I have to say, I have two pairs of the Girl Crush flares and they’re seriously amazing.

  3. Whoa, that’s the first outfit that has really got me thinking about buying flares…..they seem so….boho….or something…..which is so not me….but that outfit, THAT I could do!! Only problem is finding a good pair that fit my 5’1″ short legged self (no good tailors around….tiny town…..)……

  4. Just bought the leopard print boots and can’t wait for them to arrive! Starting a new job next week so I could justify it LOL. FYI they’re $60 on but they also have an extra 20% off right now, plus 15% if you’re a new customer. So I got them for $45 including shipping – woo hoo!!

  5. I’ve been struggling to get my head around flares because heels…ugh. But that last outfit is soooooooooooooo right on. Somewhere in my head the Ramones are now playing. Or something. Also, black Calla lilies were my wedding bouquet. Love.

  6. Shana! Outfit #3 is just utter perfection. I picked up a pair of black flares from Express recently after seeing you rock the heck out of them, and this last pic is convincing me that I did the right thing. Also: that outfit/haircut combo is giving me major Carrie Brownstein vibes, and that is a clear WIN. Yaaaaaaaaaaasssss.

  7. I don’t mean to intrude…. I’m trying to find a Iro Tamie leather jacket and saw a reference to your jacket sz 38. What size top are you? I know you mentioned you bought a size bigger to allow for layering. I an looking for the same fit. Any information you can give would be greatly appreciated! P.S. Love your blog!

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