5 Fall Occasions, 5 Fashion Tips—Delivered Straight from a Stylist

“Floral dresses are hopelessly romantic, so look for one in a deep fall shade, like plum or emerald,” says Lauren. And if you go for classic black, introduce a fun texture into the mix, like velvet. “Tea-length or longer feels right for the cooler temperatures. If you’re more modern, try a jumpsuit. Just like dresses, these come in so many silhouettes that you can find one that works for most any body type.” And get this: Trunk Club stylists curate looks for specific events, so if all you need at the moment is a new getup for your friend’s nuptials, you can work with a stylist like Lauren to build the perfect reception-ready look. The best part? You can visit a Clubhouse in Boston, Chicago, Dallas, Los Angeles, New York City or Washington, D.C., to meet your stylist and try things on in person.

Here’s where fashion meets function. “It can get warm trekking around in the sun, so this is all about layers,” says Lauren. “Start with a flattering pair of black stretch denim that’ll move with you as you’re scooping up apples and pumpkins. Top them with a printed blouse, a soft suede moto jacket and a chunky knit scarf so you can adjust to the temperature while still looking chic enough for those family photo ops.” Use a bold crossbody—yet another piece that’s photogenic and practical—to punctuate any outfit that falls on the simpler side.

Whether you’re exploring museums or taking a much-needed break from the hectic back-to-school season, you never know where days like these will take you. For this reason, it’s all about polished comfort. Lauren suggests starting with low-heeled booties, since they make for great walking shoes. “You can never go wrong with a pair of skinny jeans. Then, try a blazer with a cashmere sweater—it’s sophisticated enough for cultural activities, but still casual enough for a nightcap out with the girls,” says Lauren. Look to Trunk Club’s Girl’s Night Out Trunk: It’s full of killer looks your stylist can help you narrow down for an upgraded set of go-to outfits.

Lauren’s best advice: “Two words: stretch fabrics.” She elaborates, “Try stretch denim with an oversize sweater for a casual get-together or a stretch wool or jersey dress for a more formal dinner.” (Psst, check out Trunk Club’s denim guide to find the best fit for your body. The stretch section was practically made for turkey time.) Lauren also has this reminder for all of us dessert lovers: “If you opt for garments that aren’t super formfitting, you’ll thank yourself when you decide to go for that second slice of pie.” Girl after our own heart.

Take note, nature lovers: “This is one of the few times we say no to cotton,” says Lauren. “You’ll be much more comfortable in high-tech performance fabrics that can help your body retain warmth or cool down, depending on the temperature outside.” We love the combo of solid leggings with a retro windbreaker.