10 Cool Loafer Outfits That Prove They Go With Everything

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Wondering what to wear with loafers? Check out our 10 favorite ways of wearing loafer outfits that will get you looking stylish in no time!

In the vast realm of fashion, finding the perfect shoe to complement your ensemble can often be a daunting task. However, amidst the multitude of footwear choices, one timeless classic stands out as a versatile and sophisticated option: loafers. Loved for their comfort, elegance, and effortless style, loafers have become a staple in many women’s wardrobes.

Whether you’re aiming for a smart casual look, a professional office attire, or even a chic and relaxed outfit, loafers can seamlessly elevate your style game. These versatile shoes effortlessly bridge the gap between formal and casual wear, making them an essential addition to any fashion-savvy individual’s collection.

In this article, we explore some of the best and most practical ways to wear loafers, whether you’re styling tassel loafers, chic black penny loafers, or a trendy pair of loafers with chunky soles. From traditional workwear outfits to preppy takes on the shoe, we’ll delve into the art of pairing loafers with various garments to create stunning ensembles that exude that cool, French girl vibe.

Whether you’re a seasoned fashionista looking for fresh inspiration or a newcomer eager to embrace the enduring allure of loafers, this guide will serve as your go-to resource for unlocking the full potential of this classic footwear staple.

What To Wear With Loafers

1. Oversized Blazers

Oversized blazers and loafers make for an effortlessly chic combination that’s perfect for both in and out of the office.

The pairing is a testament to the timeless appeal of contrasting styles; the oversized blazer adds a touch of nonchalant coolness to the outfit, while the loafers inject a hint of tailored polish.

This outfit is particularly well-suited for smart-casual occasions, where you want to strike a balance between looking put-together and feeling comfortable. Whether you opt for a monochromatic look or experiment with patterns and textures, the oversized blazer and loafers combination offers endless possibilities for expressing your personal style in a fashion-forward and effortless manner.

As for your bottoms, we recommend opting for a pair of ankle-length jeans or trousers that aren’t skin-tight for a coherent look.

recreate the look
Light blue heels with silver crystal details

Catrina Blazer

At Reformation

Black Everlane ankle length trousers

The Dream Pant®

At Nordstrom

Celine monogram Ava bag

Ava Bag

Secondhand at Fashionphile

2. Ankle-Length Jeans & Pants

As we’ve already alluded to, our favorite jean cut to wear with loafers is the ankle-length jean. This style of jeans and pants creates a visual separation between your loafers and bottoms, which makes the overall outfit appear more put together.

Secondly, whether it’s a classic pair of blue denim jeans or tailored trousers, the cropped length allows the loafers to become a focal point of the outfit, allowing the loafers to take center stage.

If you don’t own a pair of ankle-length pants, you can always cuff your regular-length pants and jeans for the same effect.

To style the overall look, we recommend going for a sockless look, and accessorizing with a casual sweater or blazer if that fits your aesthetic better.

recreate the look
Black and white Totême sweater

Stripe Wool Blend Turtleneck Sweater

At Nordstrom

Agolde Riley Long Straight jeans

Riley Long Straight Leg Jeans

At Revolve

Black Bottega Veneta The Pouch Leather Clutch
Bottega Veneta

Small The Pouch Leather Clutch

At Nordstrom

3. High Socks

If workwear outfits aren’t your style, try pairing your loafers with a pair of high socks to create a cool, preppy outfit that fits right into the so-called old-money aesthetic that has recently become a major trend.

We recommend styling this aesthetic with other typical preppy wardrobe staples, like turtlenecks, crewnecks, button-down shirts, mini skirts, and tights… all of these elements are great for a modern look. Also, make sure to pick a pair of chunky loafers or penny loafers to fully embrace the style.

recreate the look
Cream silk button up shirt

Milano 100% Silk Blouse

At Ravella

French Connection

Crolenda Faux Leather A-Line Skirt

At Nordstrom

Brown Staud Moon bag

Moon Bag

At FarFetch

4. Style Them As A Statement Piece

While loafers are usually very understated, the right design or color can add an interesting visual effect to your look, truly making your outfit pop.

Whether that means styling contrasting colors like black and white as featured above, or opting for a statement shoe with an eye-catching detail, like these chain-embellished slippers from JW Anderson, don’t shy away from this tip before you try it.

recreate the look
Houndstooth cardigan
Tory Burch

Jacquard Viscose cardigan

At Tory Burch

Black cropped slim fit pants
Veronica Beard

Renzo Pant

At Veronica Beard

White YSL loafers
Saint Laurent

Le Loafer Monogram Classic Penny Loafer

At Net-A-Porter

5. Straight-Leg Jeans + Trench

A trench coat with jeans and loafers is a classic and effortlessly chic combination that embodies a classic London look.

The trench coat, much like the loafer, is a wardrobe essential that can be worn from season to season, and adds an element refinement to the outfit. When paired with straight-leg or skinny jeans, loafers and a trench create a stylish contrast that balances the formality of the two with the laid-back nature of denim.

This combination is perfect for transitioning between seasons, as the trench coat provides light protection against the elements while maintaining a stylish and put-together look. It’s a go-to option for a variety of occasions, from casual outings to more polished settings, where you want to make a fashion statement while feeling comfortable and sophisticated.

recreate the look
Tan trench coat
Abercrombie & Fitch

Oversized Nylon Trench Coat

At Abercrombie & Fitch

White Frame oversized shirt

The Oversized Button-Down Shirt

At Frame

Black croc effect YSL Sac De Jour bag
Saint Laurent

Croc-Effect Nano Sac De Jour Bag

At Saint Laurent

6. Sweater Vest + Tennis Skirt

If simply adding a pair of chunky black loafers with high socks to your look isn’t preppy enough for your style, consider pairing a sweater vest with a short pleated skirt with your loafers. This is an incredibly chic way of styling your loafer shoes that is quite different to the other styles featured in this article, especially if you stick to light and neutral tones.

Finish off your look with a matching handbag, and make sure to wear a crisp white shirt under your sweater vest.

recreate the look
White pleated tennis skirt
Amanda Uprichard

X REVOLVE Linen Dixon Skort

At Revolve

Beige cable knit sweater vest

Cable Knit V-Neck Sweater Vest

At Express

Beige Chanel 19 Bag

19 Bag

Secondhand at Fashionphile

7. Long Sundresses & Skirts

Long sundresses, whether maxi or midi dresses, are a great choice for a laid-back, classic look that exudes an effortless vibe that perfectly complements the laid-back appeal of loafers. The unexpected combination creates a visually interesting contrast that balances the casual and the refined, resulting in a fashion-forward ensemble.

Simply choose a light-colored midi or maxi dress and style it with a pair of black leather loafers for an edgy look, or alternatively, opt for cream, tan or brown loafers for a less contrasted outfit that’s great for casual weekends.

recreate the look
Long white cotton sundress

Cutout-Waist Midi Shirt Midi Shirt Dress


Black Chanel Trendy CC bag

Trendy CC Bag

Secondhand at Fashionphile

Black Prada loafers

Logo Penny Loafer

At Nordstrom

8. Long Coats

Long coats pair with loafers just as well as blazers do. It’s a classic winter and spring combination that’ll have you feeling like a fashion Influencer in no time.

High-quality wool coats in neutral colors, including black, grey, cream and houndstooth are especially trendy this year, so we would recommend adding one of those to your cart if you don’t own one yet.

recreate the look
Long grey wool coat
& Other Stories

Relaxed Wool-Blend Pile Coat

At & Other Stories

Abercrombie jeans
Abercrombie & Fitch

Ultra High Rise Ankle Straight Jean

At Abercrombie & Fitch

Black Dior loafers

Code Loafers

Secondhand at Fashionphile

9. Stirrup Leggings

For a casual yet polished look that combines comfort with style, pair black stirrup leggings with your loafers. To add even more structure to your look, you can throw on a tailored blazer and finish the look with a statement bag, like featured above. Add a pair of minimalist neutral or white loafers to complete the ensemble.

Alternatively, for a more relaxed and sporty vibe, pair your stirrup leggings with a cozy oversized sweater, experimenting with different textures, colors, and patterns to add your personal touch to the casual outfit

recreate the look
Blackoversized wool coat from Other Stories

Stirrup Leggings

At Nordstrom

Black structured blazer with shoulder pads

Harley Boyfriend Blazer

At Dissh

Beige suede loafer

Women’s Suede Loafer

At Aerosoles

10. Baggy Jeans

Straight-leg and ankle-length jeans aren’t the only way to wear your loafers with jeans; baggy jeans and mom jeans work remarkably well with this shoe style too.

While you can experiment with multiple different tops, from bralettes to casual t-shirts and more, we’re particularly fond of the structured jacket above, which creates a stylish contrasting effect when paired with a baggy pair of pants.

recreate the look
Blue baggy jeans
Citizen Of Humanity

Annina Trouser

At Revolve

Black cropped tweed jacket wit buttons

Meredith Jacket

At Ba&sh

Black Hermes Kelly 20 bag

Mini Kelly Sellier 20 Bag

Secondhand at Fashionphile

In conclusion, loafers are undoubtedly a versatile shoe choice that can elevate your style game to new heights. Whether you’re aiming for a smart-casual look or a more formal ensemble, loafers have the power to effortlessly enhance your outfit.

So, whether you’re attending a business meeting or heading out for a casual outing, don’t underestimate the power of a classic loafer. Let them be the statement piece that adds a touch of elegance and refinement to your outfits, while ensuring your comfort throughout the day.

Whether you’re aiming for a smart-casual look or a more formal ensemble, loafers have the power to effortlessly enhance your outfit.

So, whether you’re attending a business meeting or heading out for a casual outing, don’t underestimate the power of a good pair of loafers. Let them be the statement piece that adds a touch of elegance and refinement to your outfits, while ensuring your comfort throughout the day.

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