The temptation of trends might be the strongest when a new season rolls around – shiny new arrivals make the front page of your favorite retailer’s websites, and it’s easy to get pulled in by the fresh and exciting pieces that have just been released. However, what’s even more gratifying than indulging in the latest trends? Knowing that you’ve built a timeless wardrobe that you can go back to again and again every year and still love just as much. When it comes to fall/winter outfits, these are the 10 pieces that are anti-trend – in other words, they have the lasting power to deserve a spot in your classic capsule wardrobe.
1. A Wool Coat
aritzia
The Only Coat – Wool Cashmere
A wool coat might just be one of the most important pieces of outerwear that you can have in your capsule wardrobe. That’s because a wool coat can be styled to fit any occasion that you need it to this fall and winter. Need to dress in a professional way for the office? A wool coat has you covered. Heading to a holiday party? A wool coat is the perfect choice. Want a cozy layer to throw on over leggings and a sweatshirt to run errands? A wool coat adds a touch of class and sophistication to your casual outfit.
It’s not hard to see why a wool coat is so important for a lasting capsule wardrobe. However, quality and fit make a big difference! Choose your coat carefully, and select a neutral color that will complement your personal color palette and the other pieces in your capsule wardrobe. Also, make sure it fits well – if you’re tall or petite, choose sizes meant for you – otherwise, this coat might not flatter your height. If you can, look for high percentages of wool in your coat – that way you know it’s made with quality materials, and will hold up well year after year of wear.
coat | shirt | skirt | bag | tights | earrings | shoes | watch
2. Straight-Leg Jeans
madewell
The ’90s Straight Jean
Another staple for your fall/winter outfits that won’t ever go out of style? Classic denim! Of course, there are so many colors, cuts, and styles to choose from… To help narrow things down, try sticking to slim-cut, straight-leg, and wide-leg versions in the wintertime. Look for pairs with no holes, rips, or embellishments if you’re going for a classy look.
When it comes to styling your classic denim, it will all depend on the style of jeans you reach for that day! Different types of jeans look best with different shoe styles, so take that into consideration when you’re planning your outfit. You’ll also want to pay attention to the visual weight of your jeans – if you go for a looser, wider-leg pair, you might want to stick to a top that’s closer-fitting or can be tucked in. Two oversized pieces might overwhelm your frame. The same formula goes for your slim-cut jeans, too. Try to balance out the slim-fit with a top that has more visual weight, or layers!
shoes | jeans | top | coat | scarf | bag
3. A Classic Cardigan
everlane
The Crew Cardigan in Alpaca
Cozy sweaters are basically synonymous with fall/winter outfits – but not all sweaters are created equal! If you’re looking for investment pieces that look as great as they feel, pay close attention to fabric composition. Contents with high percentages of wool, cashmere, cotton, etc., tend to feel better on the body and look more flattering than their synthetic counterparts. They also tend to look more expensive and will hold up better over time with the proper care.
A classic cardigan is the perfect choice to start with if you’re adding to your capsule wardrobe. And if you already have one you love, you’re headed in the right direction! A cardigan is especially versatile because it can be worn as a top when buttoned all the way, partially buttoned and worn over a white t-shirt for contrast, or tied around your shoulders for an extra layer in case you get cold later on.
shoes | pants | sweater | bag | earrings
4. Ankle Boots
nordstrom
Marc Fisher Pointed Toe Bootie
Of all the shoe options on the market, a pair of black leather ankle boots will never steer you wrong. This classic style of boot remains popular year after year. It’s sleek, chic, and practical for messy winter weather. It keeps you warm while also giving you a modern, clean look for your fall/winter outfits.
The great thing about the black leather ankle boot is that it comes in so many different variations. Depending on your preferences, you can choose a pair with a block heel, stiletto, or no heel at all. There are also options when it comes to the toe silhouette, with styles offered that are pointed, rounded, or square. For a modern take on this classic style, I would recommend going with a pointed-toe or a square-toe version – these tend to look more flattering on most people!
When it comes to styling the ankle boot, these look great with longer pieces – think maxi skirts, long dresses, or jeans. As for what style of jeans to pair with them, try a wide-leg or straight-leg version.
ankle boots | jeans | bag | belt | sweater | coat | earrings
5. A Sweater Dress
H&M
Classic Rib-Knit Dress
A classic sweater dress always makes the list when it comes to the best styles of dresses for fall and winter outfits. You get the classy, feminine look of a dress, all without sacrificing the warmth and coziness of your favorite knits. What’s not to love about that?
If you’re going for a flattering look, try a style with vertical ribs – these help to elongate your shape. The dress featured here also has a slight tuck at the waist with an a-line skirt, which will help to highlight the narrowest part of your natural waist.
With a shorter sweater dress, you might want to opt for a tall boot to provide extra coverage – sheer black tights would also help! Then add your extra layers, like a wool coat, classic accessories, and a leather bag. If you’re looking for Thanksgiving outfit ideas, make sure to save this inspiration for later.
dress | coat | boots | bag | earrings | headband
6. A White Oxford Shirt
j.crew
Étienne Oversized Shirt in Lightweight Oxford
Next up on the list: an Oxford shirt. This classic button-up style is a must-have for your fall and winter wardrobes. You can style it on its own with jeans and a neck scarf for a Parisian-approved look, or use it as an additional layer underneath your favorite sweaters.
This is another style that is ideal for both work and the weekend. An oversized version is perfect if you plan on styling it in a more casual way, or tucking it in for work.
loafers | socks | jeans | shirt | sweater | scarf | earrings | bag
7. A Lady Jacket
j.crew
Bridgette Lady Jacket in Houndstooth Wool Blend
For those who are inspired by the classy, elegant women of the past, like Jackie Kennedy or Audrey Hepburn, a lady jacket is another must-add to your capsule wardrobe list for the colder months. This style of jacket has just the right amount of structure to make it look elevated and sophisticated, without being too stuffy. You can still style it with jeans on the weekend for brunch with friends, and it won’t look out of place.
If you’re dressing for a big meeting, try pairing the structured jacket with something a little looser and flowier, like a satin midi skirt or wide-leg trousers. These pieces will complement each other perfectly. Then add in classic, vintage-inspired accessories like pearl and gold earrings, a bracelet watch, and slingback heels.
skirt | jacket | shoes | bag | watch | earrings
8. A Black Mini Skirt
everlane
The Dream Mini Skirt
A black mini skirt can be the foundation of nearly any fall or winter outfit! If you want to dress up a casual jeans look, just swap out your denim for a mini skirt instead. You’ll elevate your outfit with nearly no added effort. And the best part is, a black mini skirt won’t break the bank either. You’ll just want to make sure you have a pair of tights handy, otherwise you might be a little cold in your fall and winter outfits!
You can wear a mini skirt at any age if you’re comfortable doing so – it might just take a little trial and error to find a length that works for you and your personal style. And if you just don’t love the above-the-knee look, try exchanging it for a midi or maxi version instead.
boots | skirt | sweater | coat | earrings | bag
9. Loafers
madewell
The Grayson Penny Loafer
We’ve already covered ankle boots, but there’s another style of fall footwear that makes this list: loafers. Loafers are another shoe that instantly adds polish and sophistication to any outfit. Plus, they abide by any office dress code, but still look great with jeans, too.
If you want to style your loafers for fall or winter, try pairing them with tights or crew socks. This will make them more comfortable and will keep your feet from freezing! For a casual chic weekend look this fall, pair them with dark-wash denim, a white t-shirt, and a collared sweater. It’s the perfect preppy vibe for visiting a bookstore or enjoying a fall shopping day.
loafers | jeans | bag | t-shirt | sweater | sunglasses | earrings
10. An Oversized Blazer
everlane
The Oversized Blazer in Buttersmooth
Speaking of academia-inspired looks, think of a blazer as your denim jacket’s cool, more sophisticated older sister. An oversized blazer is the responsible one who does her own taxes, but also stays out late on the weekends! She’s just as comfortable in a board meeting as she is meeting up with friends for happy hour, and looks stylish and polished no matter where she’s mingling.
An oversized blazer is an instant upgrade to your more casual fall jackets – but the best part is, the oversized, slightly more relaxed fit means it’s appropriate for lowkey days, too. Pair it with trousers and heels during the week, styling it with classic denim and boots on casual Friday, and dress it down with a mini skirt and t-shirt for a fun fall weekend with friends.
boots | jeans | bag | watch | shirt | blazer | glasses
Fall & Winter Staples That Will Never See a Donation Bin
These 10 staples are the pieces that will survive every seasonal closet clean-out, and won’t ever look outdated or cringey on your cold-weather Pinterest board. Over time, you’ll come up with more and more ways to style them that fit your personal aesthetic. These are the staple pieces that just keep giving, and that we can’t get enough of!
If you feel like you have the staples covered, you might be ready for a little refresh this season! Up Next: 9 Fall Clothing Pieces That Will Refresh Your Fall Wardrobe




















