Trick or Chic? Eight Classy & Feminine Looks for This Halloween

By Lillian Ferrell

Every October, Halloween returns as a spectacle of extremes: hypersexual, hyperironic, and hyperdisposable. It’s always part hustle for Instagram content, part last minute panic-ordering on Amazon, and part cultural acceptability test. What was once a holiday of colorful imagination now feels more like a race for the most meme-worthy or scantily-clad. But for women with standards, who likely dress with conviction the other 364 days of the year, why not carry that intention into the spooky season?

This 31st, whether you’re headed to a costume party or simply looking to mark the occasion, a chic and classy outfit is always in. Halloween offers something more than costume clichés. It’s an opportunity to dress up your values and embody grace, charm, and nostalgia. This Halloween, piece together the most stylish elements already in your wardrobe for a showstopping costume that’s modest, feminine, and effortlessly memorable.

Breakfast at Tiffany’s 

What film better captures the timeless elegance of Audrey Hepburn than Breakfast at Tiffany’s. In it, she plays aspiring socialite Holly Golightly. Channel her signature look with a classic little black dress, oversized sunglasses, and a strand of pearls. To complete the 1960s American glamor, add white or cream opera gloves, a simple updo, fluttery doll lashes, and rosy blush.

Regency Era Elegance

Step into Jane Austen’s world and dress as one of her beloved female characters. Whether you emulate the demure and witty Elizabeth Bennet in Pride and Prejudice or the practical and poised Elinor Dashwood in Sense and Sensibility, you’ll be the picture of modesty and grace— what Austen herself called “that which no time can impair.” Select a full-length skirt or empire-waist gown with puffed sleeves, delicate lace, silk buttons, or ribbons. Soft pastels or floral prints pair beautifully with a spencer jacket or cropped cardigan— transporting you to the English countryside of the Regency era. Add ballet flats, kitten-heeled boots, hair ribbon, and soft curls. To highlight the romantic aesthetic of Austen’s novels, opt for subtly pinched rosy cheeks, a lush lip tint, and natural gel-defined brows.

Balletcore

More than leotards and legwarmers, the ballerina aesthetic is about composure. Inspired by the elegance of a ballerina, this costume captures the quiet confidence of a woman who moves through life with her chin held high. To accomplish this look, you’ll need only a blush or ivory wrap top or cardigan, a flowy chiffon or tulle midi skirt, and ballet flats or low block heels. Style hair in a clean slick-backed low bun or ribbon-tied ponytail. Add pearl studs, sheer tights, and a delicate gold necklace. Graceful and refined— precisely what ballet is.

The First Lady File

The First Lady look is a tribute to fashion, feminine diplomacy, and the art of communicating through style. From Nancy Reagan’s Americana aesthetic to Melania Trump’s refined minimalism, conservative former first ladies left no shortage of inspiration, including for Halloween. To sport Nancy’s patriotic 1980s look, choose a tailored red or navy midi dress and a skirt suit. Finish with some gold jewelry, a simple clutch, a silk scarf, and modest heels, topped with soft curls, red lipstick, and light blush.

For looks that blend modern sophistication and it-factor with classic Americana elegance, look no further than those of First Lady Melania Trump. Melania’s style is the epitome of class with structured silhouettes, neutral tones, and quiet luxury. Focus on a camel or cream coat or sheath dress, a cinched belt, and nude pumps or heeled boots to complete her look. Add in a clutch, American flag pin, or minimalist gold jewelry. Soft waves or sleek straight hair tie the entire ensemble together in First Lady fashion. 

Went Out West 

Cowboy culture and western core have captured the fashion industry, as evidenced by Vogue’s exclusive with Kendall Jenner and Gigi Hadid and the return of red leather cowboy boots. To achieve a look that pays homage to God and country and the women of the frontier, find a denim or floral midi dress, a crisp white blouse or rugged button-up, and boots made for more than walking. Top it off with a silk scarf, turquoise studs, or vintage cross jewelry that says, “she knows the land and the Lord.” Go for natural, bronzy makeup and a braid tied in leather or a bandana-wrapped pony.

Modern Maverick 

Faith, femininity, and freedom to fly— patriotism never goes out of style. This aviator-chic look channels the woman who salutes her country. Wear a red vote to match your red vote, as well as an all-American made leather jacket in the spirit of Top Gun. Pull this look together with an olive green jumpsuit, white blouse and feminine trousers, or a tan bomber or leather jacket. Topped with aviators and a sleek bun, this feminine take on Tom Cruise is classic Hollywood meets American freedom. Melania herself showcased this look at the U.S. Navy’s 250th anniversary celebration. A true Rosie the Riveter. 

Hey, Upper East Siders

No costume edit is complete without a mention of Manhattan’s most high–fashion BFFs, Serena Van Der Woodsen and Blair Waldorf from Gossip Girl. To channel Blair, start with a pleated skirt, crisp white blouse, and silk bow-tie layered under a cardigan or cropped jacket. Add a polished headband, pearls, lace tights, and Mary Janes to complete the look. Serena’s style is more undone— think thigh-high boots, slouchy blazers over silky slip dresses, and oversized statement bags. Hair is always blown out, accessories always intentional. It’s preppy, poised, and perfectly “xoxo, Gossip Girl.”

The 90’s Rom-Com Lead

She’s the heroine we all rooted for— the bookshop owner, the coffeehouse conversationalist, or the journalist with luscious hair and a sensible handbag. The 90’s rom-com woman is clever, kind, and traditionally feminine. From When Harry Met Sally to Notting Hill, there is a treasure trove of 90s rom-coms featuring cozy, clever, and chic female protagonists. Think Meg Ryan in You’ve Got Mail: a midi skirt, soft knit cardigan, ballet flats or loafers, and a tote that looks like it could carry both a laptop and a love letter. Add gold hoops or pearl studs, a silk hair ribbon, and minimal makeup— just flushed cheeks and a pink lip.

For Runaway Bride, swap in a white sundress, a denim jacket, and cream ribbons in your hair. Sneakers or white flats keep it casual, while a bouquet of farmer’s market flowers or a takeaway coffee cup adds the perfect prop. A 90s rom-com look is your own personal love letter to layered cardigans, second chances, and women who know what they want (but still love a happy ending).

This Halloween, you can go sultry, spooky, or scary... But nothing turns heads quite like classy.

Trick or chic?

You know the answer.

Lillian Ferrell is a sophomore English major at Hillsdale College in Hillsdale, Michigan. She is studying classical opera and French in addition to English. She is a member of Hillsdale’s Kappa Kappa Gamma sorority, and is the marketing and operations director for Hillsdale’s Federalist Society chapter.