Having been a stylist for over 12 years, I'm asked the same questions a lot, and one of those is, "What shoes should I wear with [insert trouser style here]?". More recently, it's been what flat shoes look best with trousers. Aside from the other queries I receive (which usually have to do with wedding guest outfits and the best jeans), it's clear that many people are often curious about whether different shoe styles look better over others with specific types of trousers.
It has long been a tricky task to know what shoes to style with certain outfits, and whilst you can usually sling on a pair of heels with most trousers or jeans, flat shoes require more thought. Considering that most of us don't want to be tottering around in mega-high heels, it's helpful to know ahead of time which flats to throw on as you run out on your commute in the morning.
A lot of this is down to personal style, but there are some trousers and flat shoe pairings that, well, just look better than others. Although I do appreciate an unlikely duo (like Anne-Laure Mais in tracksuit bottoms with mesh ballet pumps), I'll always rely on the classics. Considering you most likely already own a lot of these trouser styles, like linen pants and wide-leg jeans, and have many of these shoe styles, including loafers and chunky sandals, you shouldn't have an issue re-creating these effortless combinations.
So, without further ado, here are some of the best flat shoe and trouser outfits for working flat soles into your usual rotation.
The Best Flat Shoes to Wear With Trousers
1. Barrel-Leg Trousers + Clogs
Style Notes: If you're struggling to style the barrel-leg trend, try pairing it with a casual shoe to ease yourself in. For example, Birkenstock's Boston clog. There's something about this duo that manages to feel put-together yet effortless, as shown by Francesca.
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The perfect throw-on jacket.
White breaks up the shades of green nicely.
These will also look so good with trainers.
These hero slide-ons aren't going anywhere.
2. Relaxed Denim + Trainers
Style Notes: As far as casual outfits go, it doesn't get more classic than trainers and relaxed jeans. I love that Indira chose a pair of flat-soled sneakers that are slightly more interesting but still neutral in colour. The addition of the leather jacket makes this a perfect outfit for transitional wear into autumn.
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I love this blend of blazer and leather jacket. It's sophisticated enough for more elevated occasions but still has that cool factor.
This shade of denim is easy to style as it matches with various colours.
Flat-soled court shoes have taken over trends in the last couple of years.
The shape and colour of this handbag are sure to last you for many seasons.
3. Cotton Trousers + Sandals
Style Notes: Whether you love a pair of straight-leg cotton trousers or those that lean cargo-style pairs with cinched ankles, it can be tough to find the ideal pair of shoes to wear with them. Lucy's outfit is wonderful inspiration. It's minimalist but elevated. When you have a neutral top and trousers, a sleek sandal is key. But what really ties this altogether is her silver bangle that matches the hardware on her sandals.
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I'm a huge fan of this editor, stylist and influencer favourite T-shirt.
A very cool pair of trousers that you can dress up or down.
Sandals with gleaming hardware are essentially jewellery in shoe format.
A piece like this goes with nearly any outfit you put together.
4. Baggy Jeans + Rhinestone Ballet Flats
Style Notes: Ballet flats (in any form) are sticking around this season, but I'm spotting rhinestone-embellished pairs more than ever right now. Adding that certain je ne sais quoi to baggy jeans, it's an unlikely pairing the likes of minimalist Lois Sterling (above) can't stop wearing.
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Waisted silhouettes are still having a moment, whether you like a blazer or cardigan in this cut.
COS jeans are always have such a good fit.
These beauties keep selling out, so grab your size when you see them.
Dragon Diffusion woven bags have a superb standard of quality.
5. Linen Trousers + Chunky Sandals
Style Notes: Linen-trouser weather has arrived, and I couldn't be happier. I really enjoy the juxtaposed look of these soft, lightweight trousers worn with heavy, chunky sandals. Jessica Skye has switched from "dad" sandals to an ankle-strap pair (above), and luckily, so many brands from Loro Piana to Vagabond have iterations right now.
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The perfect all-weather, all-season jacket.
Relaxed fit trousers will take you through every summer. They're always timeless.
You can find these sandals in both sleek leather and soft suede.
Such a chic shape.
6. Ecru Jeans + Slides
Style Notes: White and ecru jeans are a year-round staple in my book. Whilst you might lean on them heavily for spring and summer outfits, you can easily take them into autumn and winter with real and faux leather touches. When you're working with a bright (albeit neutral) hue like this, copy Danielle's look, which grounds the outfit through flat slides and a matching coat.
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Invest now and have a jacket you'll love for this autumn and every one after.
These also come in a short length, which is great for petites.
The Row always gets it right with silhouettes, and unbelievably, these aren't sold out yet.
A structured tote is the perfect finish touch.
7. Straight-Leg Trousers + Loafers
Style Notes: Whilst loafers give miniskirts a preppy feel, sometimes they can be trickier to team with trousers. Often, it's easier to wear them with straight pairs (Caroline Lin has nailed it in the above look) that show off the whole shoe rather than just having a chunky toe popping out the bottom. You could even go for a slight crop and wear them with socks to still achieve a hint of preppy.
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Everyone needs a great trench coat for both autumn and spring.
Mix different neutrals shades for a chic tonal look.
If you love the barrel leg silhouette, linen trousers offer another chic way to style it.
The toe shape and gathered seam make these much more interesting than your average pair of loafers.
8. Track Pants + Mesh Flats
Style Notes: Tracksuit bottoms are back, and everyone from Adidas to Loewe has stylish iterations. We know that mesh flats have been everywhere over the last year or two, and though it might not seem that the pairing would work, it just does. I like how Anne-Laure Mais (above) has added a tailored edge to the look with a waistcoat and classic Chanel bag.
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I will always adore a tailored waistcoat—it allows for so many styling opportunities.
A plain white T-shirt is perfect for layering under waistcoats.
These are firmly on my wish list. Casual but cool enough to wear with mesh flats.
The pair that launched the mesh shoe trend. I'd also wear these with light-wash jeans.
This article was published at an earlier date and has since been updated.
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