I know I’ve mentioned this before, but I’m saying it again because it’s so true: Early Winter is my favorite time of the year to get dressed. I love all the holiday parties and family gatherings to get all spruced up for, all the cozy, oversized knitwear to snuggle up by the fire in, and the fresh snow and crisp winter air is still exciting enough to bundle up in cute snow boots and winter layers and to head outdoors and play in.
In other words, fashion is just so fun for me right now. But, ask me this again come the end of February and it will be a totally different story. But for now, I am loving playing with fun, festive layers and interesting silhouettes. Here are some of my favorite outfits I’ve worn so far this month. Enjoy these pictures I took at the beginning of our first blizzard of the year.
10 Cute Outfits I’ve Been Wearing This December as a Michigander
Lately, I’ve been really leaning into the whole ’90’s Doc Martens with everything vibe’ that I thought was so cool the first time around but was a little too young to fully appreciate. Now, I’ve decided it’s time to suck it up and really go for the whole ‘Clarissa Explains it All/Blossom’ look that was really essential in first shaping my love of fashion. So, be prepared to see a lot more of these Leona Doc Martens that I am so loving right now. If there was even a small chance I thought they might look cute with what I was wearing – you can bet I tried to make it work!
Sweater (M) | Skirt (6) | Tights | Doc Martens (7)
Outfit 1: Mango Wrap Cardigan + Pilcro Boyfriend Jeans + Doc Martens
Hello, new favorite daily uniform. I love when pieces that I am really loving come together, look good together AND are extremely comfortable. I LOVE LOVE this outfit. I will be wearing this during our family holiday hangout session in Naperville this week. I will probably throw on a pretty lace-trimmed camisole like this super pretty CAMI NYC one underneath or this velvet option from GAP.
Cardigan (M) | Jeans (28) | Docs (7)
NOTES: I haven’t been much in the mood to wear mid-rise straight-leg jeans lately until I saw these bad boys by Pilcro at Anthropologie. I am such a sucker for jeans with unique and interesting details and these jeans have those in spades. They have amazing reviews, come in multiple washes, are available in petite and plus sizes and are under $150. Score!
Outfit 2: Oversized Free People Sweater + Plaid Wrap Mini Skirt + Tights + Doc Martens
We have a fun week of activities planned with my nieces in Chicagoland. The girls (Melody: age 7, Maddie: age 4) really want to go paint some Christmas ceramics at the Color Me Mine in Naperville and take some cute pictures so this is what I’m planning on wearing. Don’t worry, I’ll make sure to wear a long sleeve tee underneath so I can take off this sweater and ensure that it doesn’t drag through paint (because knowing me, there is no way I am escaping without some paint on me).
Sweater (M) | Skirt (6) | Tights | Docs (7)
NOTES: If you are buying Doc Martens for the first time, the biggest thing to know is that they run large. I am generally a size 7.5, but Doc Martens don’t do half sizes. I made the mistake of ordering a size 8 the first time around and they were way too large. The size 7 fits perfectly and usually size 7 is way to small for me.
Outfit 3: Gap Fair Isle Cardigan + Gap High Rise 70’s Flares + Doc Martens
I can’t believe I forgot to snap a picture of the side details of these Gap High Rise 70’s Flares because they are SO GOOD. I already have these Gap jeans in the contrasting seam wash option so I knew I would love these. They fit so well, the perfect amount of stretch to move around in without getting stretched out. Do yourself a favor and invest in a pair of these jeans, especially right now when they are 50% off.
Cardigan (M) | Jeans (27) | Doc Martens (7)
NOTES: These are the ‘medium indigo’ wash, make sure to check out the cool back pocket and side seam details. They have a western vibe and are totally worth the under $50 purchase.
Outfit 4: Cropped Cardigan + Daze Jeans
Okay, DAZE denim, I see you. I am absolutely obsessed with these jeans. I love the wash, the chic denim waist band and small slit pockets, and the frayed hem. They are made to fit roomy but I did find the size 28 (that I am wearing in the picture below) to be a bit too large, especially in the tummy area, so I am exchanging for a size 27. Also, they are currently 25% off and now under $100, while they last!
Cardigan (M) | Jeans (28) | Doc Martens (7)
NOTES: I am really loving Mango right now, especially for their knitwear. They are my go-to brand for affordably chic styles and closet classics like this cropped cable knit v-neck cardigan.
Outfit 5: Gap Velvet Burnout Mini Dress + Long-sleeve White Tee + Tights + Mary Janes
Velvet burnout is another 90’s trend that I am a big fan of (I told ya I am really leaning into the 90’s vibe at the moment). I bought this cute little mini dress from Gap on a whim on Black Friday (because their sale was SO GOOD). The dress also comes in a really pretty red option that is perfect for a holiday office party.
Dress (6) | Tee (Small) | Tights | Mary Janes (7.5) | Doc Martens (7)
NOTES: Another pair of very 90’s-inspired footwear that I am currently loving are these chunky sole mary janes. I am loving how they look with mini dresses and even jeans. Best part yet, they are over 50% off and under $50! Such a cute footwear option that I didn’t know were missing from my closet.
Outfit 6: Gap Drawstring Jeans + Mango Wrap Sweater
I think it was Amy that I first saw these Gap drawstring jeans on and of course, they looked SO cute on her that I knew I had to try them for myself. I am so glad that I did because I love them. I’m hoping this wash that I’m wearing gets restocked because it is super cool and different from any other wash that I have. I love how comfy these are – they are definitely like wearing sweatpants!
Tee (S) | Jeans (M) | Wrap Sweater (M) | Leopard Sneakers (7.5) | Doc Martens (7)
NOTES: These cute Steve Madden Madrid Low Top Sneakers did not get enough love in this post for as much as I am loving wearing them. I’ve been pretty happy with just my black and grey Sambas and these leopard print sneakers are the first pair of sneaks I’ve loved enough to add into my daily outfit mix. So many fun colors to choose from, including a pretty silver option I’m also eyeing.
Outfit 7: Free People Cardigan + Pistola Cuffed Wide-Leg Jeans + Mary Janes
You probably know by now that I can never say no to a good pair of cuffed wide-leg jeans. I have been wanting to add a pair of dark wash cuffed jeans into my wardrobe rotation and I’ve been itching to try Pistola denim. I’ve been eyeing their denim for a long time now and am glad I finally gave them a chance. Pistola has so many cool jeans worth checking out and the price point is under $200. I am wearing a size 28 and feel like these run large, so I might exchange for a 27.
Cardigan (M) | Jeans (28) | Mary Janes (7.5)
NOTES: The sweet little lace trim on this Free People cardigan really called to me. I love the fitted and cropped fit. It adds a cozy yet feminine vibe to a closet essential piece. It’s also on sale right now at Nordstrom. Please excuse the snow, it’s difficult to get away from in Michigan in December.
Outfit 8: Free People Sweater + Free People Cargo Pants + Doc Martens
I’m not gonna lie, this Free People sweater is one of my most prized purchases of the last few months. It is typically more than I would spend on a sweater but it is EXACTLY what I have been looking for for years. I just know that I’ll be wearing this super high quality piece for years and years so the cost per year is worth it for me. It’s a super thick knit so it’s perfect for the coldest of cold days here in the midwest. It keeps selling out but being restocked at Nordstrom. I’ve also seen it at Amazon and Neiman Marcus it is also available to join the waitlist at Free People.
Sweater (M) | Pants (M) | Doc Martens (7)
NOTES: I’ve had these Free People Can’t Compare Slouch pants for over a year now and they are some of the coziest pants I own and I am always getting compliments whenever I wear them as well. They are very comfortable with an elastic waist band that sometimes I wear rolled-over.
Outfit 9: Mango Wrap Skirt + Mango Cropped Cardigan + Boots
This outfit is brought to you by Mango 😉 I’ve been really wanting a denim wrap skirt like this one I picked up at Mango, specifically one that ties on the side. I love the medium blue denim wash of this one but it is a little thinner quality then I was expecting and it needs a good ironing. I’ve also been eyeing this denim wrap skirt from Ann Taylor that I am thinking of purchasing while it’s 50% off, it looks very promising to me!
Cardigan (M) | Skirt (M) | Doc Martens (7) | Similar Knee High Boots
NOTES: I’m not sure the Doc Martens work with this outfit, as much as I wanted them to work – I think I prefer my pair of brown knee high pointed-toe boots that give this look a much more put together feel. But, I included the picture with the Docs for…research purposes, ha.
Outfit 10: Maeve Fitted Cardigan + Pilcro Jeans + Mary Janes
I had such high hopes for this beautiful fitted Maeve cardigan from Anthropologie. The reviews are amazing and it does create such a unique silhouette, maybe I need to swipe out the straight-leg jeans for wide leg jeans or a fitted skirt- and I am not sure these shoes go with this look at all? What do you guys think? I believe if this cardigan was shorter, I would prefer how that would look.
Cardigan (M) | Jeans (28) | Mary Janes (7.5)
NOTES: I feel like I haven’t sung the praises of these jeans enough in this post because I truly have been wearing them non-stop lately (currently wearing them as I type this). The denim fabric is: 68% cotton, 31% recycled cotton and 1% elastane. It feels lightweight but still very high quality and easy to move in.
Thanks for reading! Happy Holidays friends! Until next time,
xo, Jess ( My Instagram | More of My Posts )
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