My Fall Outfits Were Feeling Stale—12 November Outfit Ideas I’m Trying Instead

Now that the weather is cooling off, leaving the house involves grappling with the internal struggle: will I be cute or will I be comfortable today? On chilly days, the heaviest coats or most weather-proof shoes are all-too-appealing, but they don’t always show off your style in the way you might hope. Luckily, this month there are some clever ways you can meet in the sartorial middle: ensuring you don’t freeze, but still putting your outfit first.With darker evenings here, football season in full swing, and Thanksgiving around the corner, think of these 12 November outfits as the puzzle pieces to help you check the boxes for everything coming up on your calendar. Playing with bold colors, contrasting textures, and even sneakily comfy silhouettes are some of the simple ways you can make November your best-dressed month of the entire year. Check out some of my favorite looks below.A Comfy-Festive Party LookTheStewartofNY//Getty ImagesAn on-trend striped rugby sweater is the kind of dress-up-or-down staple you might usually style with jeans and sneakers. But for any dressy events on the calendar, try playing with texture and structure by styling it with a full, sequin skirt. It’s a look that reads dressy without trying too hard. Color-Contrasting Cozy StaplesTHE HAPA BLONDE//Getty ImagesOne way to make comfy pieces like oversized knits and track pants feel instantly dressy? By going bold with color. For days when you want to look polished but will mostly be relaxing on the couch, this is a great place to start.A Sunday Brunch-to-Football EnsembleMoritz Scholz//Getty ImagesIt’s prime football season, which might mean your Sunday afternoon is devoted to keeping up with your favorite team. A pair of relaxed jeans and a suede jacket is a combination that’s cute enough to wear to brunch with your girlfriends, but won’t feel out of place at a sporty party.A Little Satin SuitTheStewartofNY//Getty ImagesIf you’re the type to dress up for Thanksgiving (or any occasion really), a trim satin suit is a dressy look in stark contrast to the usual oversized staples. The shiny fabric gives the look a festive touch, while styled back to a simple black top and shoes, the overall effect is very ‘90s Prada—who can complain about that?A Travel Day LookJose Perez/Bauer-Griffin//Getty ImagesOdds are you’ll be headed out of town to spend some time with family. Your travel day look should always put comfort first, but a few small styling choices can make the outfit feel purposeful instead of schlubby. A crew neck tee paired with a V-neck sweater, a trench coat, and chunky Dad sneakers are what make Zoë Kravitz’ outfit look so good.An All White EnsembleMoritz Scholz//Getty ImagesAs winter approaches, there’s something enduringly chic about a white-on-white look. Even if your outfit is as simple as jeans and an oversized sweater, the matchiness pulls everything together. Black accessories are an easy pick, but you could also add a pop of contrast by styling the outfit with red shoes.The Secretly Stretchy OutfitEdward Berthelot//Getty ImagesCall it genius, call it sneaky; there’s no need to wear full-on sweats to the Thanksgiving table. A dressy matching set can be just as comfortable. Look for styles with a soft, stretchy plissé fabric, which has a dressed-up, flowy air but feels as easy as your coziest loungewear.Playing With TextureJose Perez/Bauer-Griffin//Getty ImagesThis time of year, fashion is all about rich, sumptuous textures and hues. Gigi Hadid’s party look puts a soft, check flannel skirt in contrast with leather boots and a matching jacket, and the effect is greater than the sum of its parts. Cozy yet chic.The All Black EnsembleEdward Berthelot//Getty ImagesWhen you don’t want to think too hard about your look, an all-black outfit is an easy fallback with polish. Try opting for an oversized knit, styled with tailored trousers and loafers for a look you could wear to the office, but would feel just as comfortable in for a Saturday spent shopping with your most fashionable friends.A Borrowed-From-the-Boys OutfitDaniel Zuchnik//Getty ImagesBreaking up a tailored look with a cummerbund or even a scarf can be an easy way to repurpose pieces you might usually relegate to the office. This dressy yet comfortable look is versatile, so throw it on for post-work martinis or even a night at the orchestra.The Dramatic LookTheStewartofNY//Getty ImagesFringe is a trend to know this season, and Nara Smith’s Kallmeyer dress is the blueprint for a festive Thanksgiving party or wedding when you want to dress to impress. The fringe detail adds movement, which makes it ideal for a situation with a dance floor. Layer a leather jacket or a black trench coat on top for your time in transit.Jeans, But UpgradedRaimonda Kulikauskiene//Getty ImagesA great pair of jeans should always be in heavy rotation, but how you style them is an easy way to make them feel fresh. Here, mixing feminine pieces with more classic menswear details gives this a casual-yet-effortful effect. Try a blazer and little heels with socks for a playful spin on pieces you likely already have sitting in your closet.Aemilia Madden is a freelance writer, editor, and consultant with over 10 years of experience in the fashion industry. She’s written for publications including Vogue, Harper’s Bazaar, Elle,The Cut, and The Wall Street Journal. She also writes a newsletter called Taeste Bud, that covers stuff we buy, places we go, and the people we want to be. Previously, she held roles at The Zoe Report, WhoWhatWear and Popsuagar. Aemilia attended the University of California, Berkeley where she majored in Political Economics. In her time away from the internet, Aemilia is probably out on a hike. You can follow her on Instagram here.