4 Go-To Outfit Formulas for Winter
I love using items from my closet to remix and put together new outfits for each season. I know many of you have requested more guides like this and I also prefer writing in a practical and helpful manner so you get the most out of your own closets and find outfit inspiration during each visit to my platforms!
Let’s get started. These outfits can be modified to fit your needs. I wear business casual during the workweek and love comfortable clothing no matter what setting I’m in. For colder climates, I recommend adding in your winter jackets/coats, fleece-lined tights and scarves to make these outfits more versatile for you.
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Solid Dress + Brown Boots + Neutral Handbag + Print Scarf or Statement Necklace
This combination is an easy outfit to throw-on. Solid dresses are easy to find but more difficult to find in styles that fit your body. This classic one from Nordstrom is great because sizing fits very well for many different body types (even pregnant ladies can wear this one!) while also hiding any area here that you’re uncomfortable with. I’m wearing size XS with no alterations and the length is also great on me without hitting below my knee (which could be a problem in other non-petite sizing). This dress also comes in classic neutral colors with new seasonal colors throughout the year. I love this rustic burnt orange color and also recommend the burgundy for fall/winter and of course the gray or black are great for year-round wear. I opted to pair a print plaid scarf with it instead of a statement necklace. Simple jewelry also works and I made this winter friendly with brown boots (they are waterproof) and finished it with a neutral handbag.
Shop for the Look:
Dress: Nordstrom Size XS (exact and sleeveless version)
Boots: Aquatalia Size 6 (similar here or here + winter socks I love with discount code)
Scarf: Nordstrom (similar here or here)
Bag: Michael Kors (newer styles here or here + handbag organizer I use)
Necklace: BaubleBar (exact or similar)
Watch: Daniel Wellington c/o (exact)
Bracelet: The Gibson Collective (similar)
Black/Gray Jacket + Solid Tee + Dark Wash Jeans + Slip-on Sneakers
This is a modified look from my Winter Capsule wardrobe. Instead of the black vest, I opted for a gray fleece jacket and added in slip-on sneakers instead of a pair of ballet flats. I like the layering option of fleece jackets and they are very warm! This outfit formula is great for weekend and casual wear and can be modified based on specific temperatures outside. The solid tee can be customized to fit your personality with a neutral, pop of color or print design. My recommendations for winter are striped tees and burgundy tees (long or short-sleeve). No worries if you do not own slip-on sneakers – any pair of sneakers works. The most important part is that they are comfortable and easy to walk in (which I can say about all shoes but this is particularly important for sneakers because style does not trump comfort). I also love these Asics that come in neutral or fun colors to pair with dark wash denim.
Shop for the Look:
Jacket: FIGS Size XS c/o (exact and use my 20% off code: FIGSxSCRIPT)
Tee: Madewell XXS (exact or similar– cozy & warm)
Jeans: Banana Republic Size 24 (similar here or here)
Sneakers: M. Gemi Size 35 (exact and lower priced version here)
Tan Cardigan + Colored Tee + Jeans + Ankle Boots + Winter Socks
I live in this fleece wrap cardigan! I love how easy it is to layer over basic tees and feel warm in colder weather (or at home lounging). Combine a neutral cardigan with a colored tee and jeans and you’re good to go! I like this tan color with burgundy but also own this wrap cardigan in a heather teal green and would pair that color with a neutral black or gray tee. Both also look great over a white tee. These ankle boots are perfect for winter and were a find from my late aunt who also wore a size 6. I like showing off winter socks with them to finish this winter look. For added warmth, you could also add in a scarf – solid or printed – and your winter coat.
Shop for the Look:
Jacket: Nordstrom XXSP (exact– on sale!)
Tee: Madewell XXS (exact or similar– cozy & warm)
Jeans: Paige Size 23 (similar here or here)
Shoes: Ugg (similar here or here)
Socks: Sheec c/o (my blog post + 20% off “PSSVIP20)
Printed Dress + Tan Boots + Opaque Tights + Simple Necklace
This is my go-to print dress. I’ve owned it for 8+ years now and it never gets old. The wrap or faux-wrap style dress is one of my favorites because it adjusts with varying weight fluctuations (or works during pregnancy) and stays classic. For winter, I paired this print dress with opaque black tights and ankle booties. I could also swap out the ankle booties for black tall riding boots and remove the tights. For those in very cold climates who also commute on public transit, you can commute in fleece-lined tights or leggings and take them off when you get to work.
Shop for the Look:
Dress: BCBG Size XS (similar here or here)
Boots: Vince Camuto Size 6 (exact– on sale! or similar + no-show socks)
Tights: Talbots XS (exact or fleece-lined– on sale!)
Bonus Style Tip: I look for dresses that don’t wrinkle and are machine-washable. I literally cannot stand going to the dry cleaners more than twice a year. Dresses made of cotton (above) feel like pajamas and dresses made of polyester/spandex are great options!
You may also enjoy reading:
- Winter Capsule Wardrobe + Free Download
- How to Wear Ballet Flats all-day long
- Best No-Show Socks with discount code
- Why I love these Work Pants 4 Years Later
Jessica Louie, PharmD, APh, BCCCP is the CEO of Clarify, Simplify, Align and Host of The Burnout Doctor Podcast. Dr. Louie uses her signature Burnout Doctor Method to coach burned out pharmacists & professionals to simplify because work-life balance is a LIE. Align work into your life & break free from people pleasing, perfectionism and thrive in life on YOUR TERMS.