Oct23
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Updated August 2026
If there’s one kind of shoe that has truly stood the test of time in my closet, it’s loafers. I first started wearing them back in my Corporate America days, when a blouse and trousers were basically my daily uniform. Fast forward 15+ years, and loafers are still one of the shoes I love most. They’ve outlasted every sneaker trend I’ve cycled through, a rotating cast of boots, and even a fling with ballet flats that’s making a comeback. Loafers are classic, and they go with almost everything I own. Nothing else in my closet has held up quite the same way.
Whether you lean preppy or a little edgy, loafers work with all of it. Jeans, a midi dress, trousers, even shorts and socks all work well with loafers. They dress up for business casual or dress down with denim. Loafers are also a good piece for building summer-to-fall transitional outfits, since they work for warm days but still hold up once the weather cools. Consider this my love letter to loafers, and every way I style them.
9 Ways to Wear Loafers This Season
Loafers + Midi Dress
This is a more unexpected duo, but loafers with a midi skirt is such a great combo. I love wearing a Hill House Nap Dress with a loafer. It’s an easy combo once the weather starts to turn, and it’s one of my favorite looks in my fall outfit ideas post. Sleek leather loafers like these Sam Edelman Loraine Loafers are typically my favorite. Penny loafers, like the Madewell Grayson Penny Loafer, keep the look timeless, and chunky loafers like these Sam Edelman Leah Platform Loafers can also add an edge if that’s more your style.
Loafers + Straight-Leg Jeans
A straight-leg jean is one of my favorite ways to wear loafers. Look for a cropped or ankle-length jean so the loafer shows instead of disappearing underneath. I styled the Petite Studio Bentley Straight Cropped Jeans with the Sam Edelman Loraine Loafers in black, since the gold bit hardware adds a nice detail without competing with the jeans. A cozy cardigan like the Petite Studio Carmina Wool Cardigan and a structured bag like this A. Soliani Tote round it out for something easy to throw on. If you’re looking for the best straight-leg jeans, I have tried plenty and rated them in a blog post.
Loafers + White Jeans + Blazer
Loafers, trousers, and a blazer feel timeless together. This is the outfit that first hooked me on loafers. This Petal & Pup Plaid Blazer over a simple white top instantly elevates it, especially cinched with a leather belt at the waist. These Amazon White jeans keep it fresh, and I add the Serena Cognac loafer last. I also throw in my Cuyana tote bag here, mostly because the leather matches the loafers, and I like things to match.
Loafers + Socks
I know what you’re thinking: socks with loafers? Really? Yes, hear me out. It’s a little preppy, but practical, and it’s one of the biggest loafer trends going into fall. White crew socks (I love these Amazon socks with the ruffle on top) with the Madewell Grayson Penny Loafers and Abercrombie barrel jeans is classic. An ankle sock with the same ruffle detail looks good with this Amazon denim dress, especially with a little peek of white against a brown loafer. Here are the best socks to wear with loafers if you want the full breakdown of do’s and don’ts.
Loafers + Mini Skirt
I think the photo speaks for itself…look how cute loafers are with a mini skirt! I may have been skeptical if I hadn’t tried it first myself. It’s classic prep with a little edge. It’s one of my classic preppy wardrobe staples. Pair this Tuckernuck plaid mini skirt with a sweater and penny loafers (Again, I recommend the Grayson Penny Loafer), or keep it sleek with this Joe’s Jeans fitted knit polo, a cream C’est Tout Skort, and the Sam Edelman Loraine Bit Loafers for a tan-on-cream finish.
Loafers + Barrel Jeans
Barrel jeans are the denim trend everyone’s wearing right now, and loafers work well with them. Proportion matters here: a fitted or tucked top keeps the barrel leg from swallowing you, and a sleeker loafer balances the volume without competing with it. This sleeveless turtleneck sweater is a good example of that, tucked in and simple. If you want more ways to wear this shape, I’ve got a full post on how to style barrel jeans.
Loafers + Shorts
When warm weather lingers, don’t put your loafers away yet. I like styling mine with tailored shorts; these A. Putnam trouser shorts are my favorite, and a cute sweater for a business-casual summer or warm fall look, or with denim cutoffs and a trench coat for weekend errands. My Grayson Penny Loafer adds a finished touch that sneakers just can’t replicate.
Loafers + Maxi Skirt + Button Down
A long flowy skirt with an oversized button-down; just half-tuck it or you’ll look swallowed. I’m wearing the Monrow Stripe Poplin Oversized Shirt with this Alice Walk Linen Maxi Skirt, a straw tote, and my go-to Sam Edelman Loraine Bit Loafers. It’s the longer, preppier version of the mini skirt look above, same shoe, different mood.
Loafers + Literally Anything
I’m not exaggerating when I say loafers go with literally anything. Jeans, trousers, mini skirts, shorts, dresses, you name it. The key is choosing the right loafer for the outfit. Tassel loafers for a classic prep look, suede loafers for texture, chunky loafers when you want something bolder, or sleek brown loafers when you’re keeping things understated. The Julia Loafers from Beckett Simonon combine brown, suede, and tassels in one shoe, so they’re basically the chameleon shoe of my closet.
The Best Loafers for Women
If you’re building your loafer collection, here are the ones worth considering:
- Everyday staple: The Sam Edelman Loraine Loafer. I’ve owned 5+ pairs in different colors and materials- leather, raffia, you name it. Nothing beats them.
- Sleek and refined: Madewell Grayson Penny Loafers in black leather. They’re the classic that never goes out of style.
- On-trend edge: Sam Edelman Leather Platform Loafer. Chunky, with a platform sole, for days I want something with more edge.
- Classic prep: The Julia Loafers from Beckett Simonon. Tassel detailing sets them apart from a plain loafer.
- Textured option: Madewell Grayson Penny Loafers in brown suede. Suede can look dressier and softer than leather, so I keep the rest of the outfit simple: denim or trousers, nothing that competes for attention.
- Easy wear: Serena Cognac Mule Loafers. No laces, just a simple slip-on and go.
Invest in at least one pair of cognac leather loafers. You’ll wear them more than you think, for years to come. From there, add variety with suede, tassels, or a pop of color.
The Bottom Line
So yes, this really has been my love letter to loafers, fifteen-plus years in, and I’m still just as smitten. If you’re building a wardrobe that’s classic and versatile, start with a loafer. Alright, I’ll wrap this up now. My own loafers are calling from the closet.
FAQs
How do you style suede loafers?
Suede is a little dressier and softer than leather, so I like to keep the rest of the outfit simple: denim or trousers, nothing competing for attention. I have the Madewell Grayson Penny Loafers in brown suede that I wear all the time.
Are penny loafers still in style?
Yes, they’re the classic that doesn’t go out of style in my opinion. I wear mine with jeans, trousers, and even with socks when the weather turns.
What do you wear with loafers?
Almost anything: jeans, midi dresses, trousers, skirts, even shorts with socks. I’ve got 9 full outfit ideas above if you want the details on each one.
Can you wear loafers with dresses?
Yes, and it’s one of my favorite combos. A loafer balances out a soft, flowy dress, especially with a midi length like the one in the first outfit I mentioned above.
Are loafers in fashion for fall 2026?
Yes, loafers are a fall staple that never really goes away, and this season especially, socks-and-loafers and suede pairs are everywhere.
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