How to Style Loafers and Get Over Ballet Flats
Loafers didn’t achieve their cool-girl status overnight. In fact, they originally found their place in office attire and prep-school closets. However, once notable designers began to experiment with them, the styles evolved—shapes became bolder, some finishes took on a shiny twist. Thanks to that, loafers transitioned from being strictly formal to becoming versatile pieces that fit into everyday outfits. This shift made it entirely natural to pair loafers with jeans, dresses, skirts, etc. Apart from that, they now come in various styles—sleek and understated, rough and chunky, designed to make a statement on their own.
So, are loafers in style? Still, after all these years? Always—we spot outfits with loafers on celebs as well as on the streets, currently more than ever. And in this article, we are gonna discuss what to wear with loafers to look chic and modern, despite their preppy past.
Loafers with jeans
You know, there's really no need for a detailed guide on how to wear jeans with loafers. This classic pairing works wonderfully in countless styles—skinny jeans with penny loafers, wide-leg pants with moccasins, and so on and so forth. However, if you aim for something hot and trendy, mix brown and ecru or white. For instance, soften a pair of brown leather loafers by pairing them with light-wash jeans, or opt for brown loafers matched with white denim.
Try the Lace-up loafers from Hereu—iconic design inspired by the classic Spanish nautical loafers. Dress your loafers street style with a pair of white Relaxed baggy jeans from Citizens of Humanity, and finish the look with a sporty jacket.
Loafers with blazer
Loafers paired with suits are a match made in sartorial heaven. Yet if your business-casual look is starting to feel a bit monotonous, here’s a simple trick to refresh your style. If you don’t own a blazer-style dress, throw on your favorite longline blazer over a button-down or a classic tee, and instead of reaching for the matching pants—skip them altogether. A blazer dress, or a makeshift version, works just as well with your loafers as a complete suit but offers a modern twist. When the colder months roll in, add tights or leggings; for spring, feel free to ditch them.
We suggest the Oversize suit blazer from Beige Brown with the Contrast-trim cotton t-shirt from Tiger of Sweden underneath. If the blazer on its own feels a bit risky, add fitted shorts to the mix.
Loafers with dress
Pairing feminine dresses with masculine loafers is a delightful way to introduce androgyny into your wardrobe. A stylish pair of loafers, along with matching tube socks, makes even the sweetest ensemble more grounded. Even though loafers may not be your go-to choice for spring and summer, they add an edgy twist to a warm-weather look. Plus, they’re a practical footwear option if you live in the city or are vacationing in an urban setting—they offer more foot protection compared to sandals.
Dresses by Erika Cavallini are perfect for such styling, like the Sleeveless belted midi dress, if you prefer something more understated. If you want a cute outfit with loafers, try the Puff-sleeve open-back dress—its mini length and powder pink color provide lovely contrast with put-together loafers.
Tailored pants and loafers
The tailored two-piece promises maximum style mileage when worn with equally poised and powerful loafers. This fail-safe coupling is filled with boardroom boss energy and street-style flair—and is well-suited for anything.
A wardrobe workhorse, neutral trousers, such as the Wide-leg suit trousers from Beige Brown, are a no-brainer match for loafers, especially when they twin in nourishing earth tones. Pair them with a blazer, or go trendier and choose the V-neck waistcoat for the top part. As for the loafers style, select something minimalist and sleek—black or brown leather, no platform, classic design.
Loafers with mini skirt
Loafers are the ultimate choice for those of you who love a statement-making look. Pair them with a mini for the perfect blend of edgy and nostalgic—embracing the ‘90s resurgence while offering all-day comfort. To take this preppy school uniform attitude further, choose a polo shirt and a small backpack instead of a bag. It's nice to reminisce about those days when the world was easier, don’t you think?
For our loafers with skirt look, we teamed the Longsleeve polo shirt from Beige Brown with the Fringed mini skirt by Lisa Yang. Your loafers here can be a bold platformed pair with chains or fringes—let your inner child express her style.
Loafers with sweatpants
Remember, we mentioned that loafers pair well with everything? Let’s revisit that idea now. When styled wisely, this classic menswear staple elevates even casual sweatpants or sweatsuits to street-style status. Bonus points for a lug sole or penny loafer. To maintain a polished look, opt for elevated basics—a leather handbag and a stylish trench—to keep the outfit in the trendy zone.
Let’s break down how to wear penny loafers with sporty chic staples. Start with the High-waist tapered sweatpants from Aeronautica Militare and throw the Long trenchcoat from House of Dagmar on top. Keep the accessories sleek and complete the look with the Cut-out leather bag from Hereu.
Loafers with shorts
If you want to exude an "impossibly cool yet laid-back" vibe, this is the outfit to go for. Start with a button-down shirt or a lightweight knit, then pair it with elongated shorts. Complete the look with tube socks and your favorite loafers—it's literally as simple as that.
The Tailored shorts from House of Dagmar fit the look ideally, yet you may wear denim Bermudas instead. We love the idea of loafers with thin soles for this combo, like Hereu’s Metallic-effect loafers—here, you don’t even have to use socks, by the way.
Loafers with midi skirt
This outfit combination is a surefire way to achieve instant chicness in two steps—simply add a fitted blazer and a voluminous midi. While many might opt for slingback heels at this point, if you're in the mood to mix it up, step out in stylish loafers for a fun, unexpected twist.
Though it may seem a bit bookish at first glance, this styling trick is a favorite among fashion insiders at fashion weeks, who infuse coolness into everything they wear. We suggest you do the same and try a trendy combo of the Collarless blazer and the A-lined silk skirt from House of Dagmar.
Loafers with cardigan
Knitwear has transformed from a once-sleepy, season-limited category into a fashion staple, and cardigans have shed their image as mere afterthoughts. Similar to loafers, cardigans have transitioned from a scholarly look to a chic piece. To pull off this cardigan-loafer ensemble, start with an oversized or elongated cardigan, pair it with a skirt or knit trousers for a harmonious connection between the sweater and the shoes. Finish off with lug-sole loafers to elevate the intended elegance of traditional shoes and introduce a chunky attitude.
For this women's loafers outfit, we combined the Open-shoulder ribbed cardigan with the Fine-knit ribbed trousers by Lisa Yang—they both feature the same ribbed texture and create an interesting silhouette reminiscent of the dress-over-pant trend.
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