Hi there! Fall and winter are two of my favorite seasons for loafers. One of the things I love about loafers is you can wear them when it’s a warm fall day or a cold winter day. There are so many gorgeous loafers for women that you can wear with a lot of different pieces in your closet, whether you’re wearing jeans or getting dressed for work.

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If you’re wondering where to start with loafers, a neutral shoe is a good idea. Brown is so popular again this fall, and I’ve been reaching for my brown loafers a lot. So, I wanted to write about different pieces you might wear with a pair of brown loafers and share some outfits.
Before we dive in, if you’re looking for general tips on loafers, including black loafers and other options, check out my blog post on how to wear loafers!
What to Wear with Brown Loafers And A Few Of My Favorite Pairs
There are so many different styles of clothes that you can wear with brown loafers, but first, here are a few of my favorite pairs. I love the tassel loafers if you want something different than traditional penny loafers.
Dark Jeans
Dark jeans are a go-to option for fall and winter because they feel a little moodier like the seasons! Plus, they tend to look nice with popular fall colors like brown. I wear my brown loafers with all different styles of jeans from straight leg jeans to wide leg jeans.
Slip Dress
A slip dress is super versatile, so it makes sense you could style this chic dress with loafers! I love to mix and match super feminine pieces like a slip dress with more edgy or masculine items like loafers. They balance each other out and give the outfit an effortlessly cool vibe. You can wear a leather jacket, lightweight jacket, blazer, or a sweater with the slip dress for a layer of warmth. There are tons of slip dresses out there, but I love this one.
Brown Socks – Or Any Socks
Don’t be afraid to wear socks with your loafers or sock tights! This is definitely on-trend, but it’s not just a trend. I’ve always loved to wear my coziest socks with my loafers to make sure my feet stay warm. I think it’s because my mom has always done that, and I saw her doing it when I was growing up.

If you’re wondering what socks to style with your loafers, you can start out simple, whether that’s just a solid pair of socks or your favorite pair you already own. I love to wear these cashmere socks with my loafers, and I recently wore this pair in green floral with brown loafers.
Brown Sweater
Brown sweaters are an obvious, easy choice to wear with brown loafers. You can wear a brown sweater and brown loafers with jeans, work pants, or a skirt – the options are pretty endless. I own each of these sweaters and highly recommend them because you can wear them in the office or out with your family on the weekend.
Denim Dress
This denim dress has been one of those dresses that I wear all the time because it’s comfortable and looks super cute on. I love that it’s long sleeve, but you can easily roll up the sleeves if you want to. It’s also super soft since it’s 100 percent cotton. Click here to see how I styled it with taupe-brown loafers. Tassel loafers are also an option to consider with a denim dress. They’re a fun detail but they aren’t overpowering, so the outfit is still timeless.

You can style brown loafers with a midi or maxi length denim dress too. A sleeveless denim dress will look so cute with a brown sweater or a silk blouse under it – I own both of these tops and wear them a ton!
Suede Shirt Jacket Or Blazer
A suede jacket is the perfect outerwear piece to wear with loafers. I own the first two and wear them constantly. Anyway, the suede against a smooth leather brown loafer is one way to add dimension to your look. And, a suede jacket will also look nice with brown suede loafers. This type of jacket is super versatile too – you can wear with it jeans or a skirt and your loafers.
Khaki Green Jacket
Speaking of jackets, this khaki green jacket is always a go-to for fall and spring. I love how it goes with just about anything, including brown loafers. While this jacket is fairly casual, loafers actually dress it up. Click here to see how I styled it with brown loafers and socks.
Grey Sweater
There are so many shades of brown and gray that you can wear together. A gray sweater looks really nice with jeans and brown loafers, whether you’re at work, taking a city vacation (like I did in a photo below), or just running errands.

Red Cashmere Sweater And Socks
I love the idea of wearing a red sweater and red socks with brown loafers around the holidays. While loafers are perfect for work, they don’t have to be a serious shoe! They’re also perfect for the holidays and the weekend in general too. Red against brown is a fun contrast. This red fair isle sweater I recently tried on (and still have in my cart) would be my choice.
Purple Coat
Shades of purple aren’t too far off from the super on-trend burgundy. I actually just love this coat in purple. And I think it would look really pretty styled with brown loafers. I always say you should consider neutrals for your coat so you can get a ton of use out of it. I also always like to have one or two fun coats that I know I’ll wear a lot even if it doesn’t match my entire wardrobe – that’s this coat!
Slip Skirt
Slip skirts are everywhere, and there are so many good options to wear with loafers, especially for the fall and spring. I love the style that hits above or right around your knee for loafers. You can wear this with a blazer, suede jacket, or a cozy sweater.
How To Style Brown Loafers
Maxi Skirt and Suede Jacket
This is an easy outfit for work or the weekend. You could also wear this with a button up shirt and a suede blazer if you want a more classic look. I think the suede bomber style jacket adds a fun edge to the look.

Gray Sweater With Light Brown, Camel Loafers
This is a casual outfit, but it’s definitely one you can wear to work if you have a casual work environment. Or, you could create a workwear look with these pants and this sweater. You can wear these loafers with any type of medium or light gray sweater.

Shop my bag in tan here and black here.
Comfortable Work Outfit
Here’s another way to wear this style of loafers for a work look. If you work somewhere that you walk around a lot but still need to dress in business casual, then these loafers are for you! They run true to size.

Monochrome Slip Dress And Loafers Outfit
Okay, once again emphasizing that these loafers are the most comfortable shoe I own, ha. Anyway, I love how this outfit works if you’re heading to an office or if you’re a busy mom who wants to look stylish – or if you’re both! The dress length is perfect for being able to navigate being out with my toddler or a child of any age.
Monochrome looks are always a good idea! And, fall and winter are a great time of the year for them because you can mix materials to add depth and dimension to your look. If you keep your shoes the same general color as your outfit, it will help you look taller! If you love monochrome, check out my blog post on monochromatic outfit ideas.
Dark Brown Loafers Outfit With Croc Bag
These dark brown loafers have a croc-embossed leather and the perfect heel height to be comfortable and polished. I have a very similar pair that I wear all the time. They also look so cute with cashmere socks when it’s cold. Croc loafers bring an elevated look to your outfit themselves, but you can definitely pair them with nicer pieces for work too. You can wear these with pretty much any bottom, whether you want to dress casually or you’re getting ready for a meeting.
I’ve been wearing my croc loafers with this croc bag, and they look so good together even though they aren’t a perfect match.
Did you find a brown pair of loafers you love? How do you plan to wear them? Let me know in the comments!





