Written By Lisa O'Shaughnessy
Founder of Always Stylish & Personal Stylist
The Best Shoes, Boots & Trainers to Wear with Jeans for Women
For my first post of 2026, I want to answer one of the questions I’m asked most by female personal styling clients. Whether I’m styling for work, events, travel or keynote speaking, this question always crops up. What shoes, trainers, boots etc work best with my jeans?
If denim forms the backbone of your wardrobe, knowing which footwear works with each jean style really matters. With silhouettes changing each season, it is not always obvious what looks right together. The key is balance across the whole outfit. This guide simplifies it, so you can choose pairings that feel right for you.
Keep scrolling to see 6 jean styles and their footwear pairings.
what shoes to wear with BARREL LEG JEANS
The key to styling a barrel-leg jean is ensuring the hemline finishes around the ankle. If you’re pairing it with a boot, choose a slim shaft that fits neatly underneath the hem with no gap. Sporty trainers can look clunky with this style, so opt for a slimmer, retro-inspired design instead.
In winter, darker-coloured socks work best with loafers and trainers, while bare feet or very fine socks are ideal for flats, slingbacks and court stilettos.
Slim-profile barrel styles can work with ballet flats, but wider barrel shapes generally do not.
what shoes to wear with STRAIGHT LEG JEANS
The most versatile jean, it works with pretty much all shoe and boot styles. Where you prefer your straight-leg jean to finish comes down to personal preference. Some women are happy for it to sit on the shoe, while others prefer it hovering around the ankle. Too long though can look messy and make many women appear shorter.
what shoes to wear with cropped jeans
This is by far the jean silhouette - from slim to wide styles - that causes the most issues, particularly as the weather gets colder. When wearing boots, you ideally want the boot to sit neatly under the hem with no gap. Gaps can throw off outfit proportions and sometimes make the wearer appear shorter.
In winter, adding socks can work well. Choose darker colours if you feel self conscious about showing them, or use socks intentionally as a contrast or colour pop, with red being a great example.
In summer, go sock free or opt for invisible socks with trainers. Avoid socks with heels and choose either bare feet or very fine socks with flats.
what shoes to wear with BAGGY JEANS
This jean, sometimes also called a relaxed or 90s style, lends itself particularly well to a more casual look. Flat shoes such as loafers work well, but they need to feel substantial. Clients who have been wearing this silhouette with a delicate ballet pump often sense that something feels off, but they don’t know what the issue is. It’s usually about balance, as baggy jeans need a shoe with some substance, and a ballet pump is too delicate to offset a relaxed, roomy jean.
Conversely, sandals - both flat and heeled - an work well with a baggy or relaxed leg, especially when paired with a fitted top half.
what shoes to wear with WIDE LEG JEANS
A great, versatile jean style that looks equally good dressed up or down. It also works brilliantly with sandals - both flat and heeled - as well as platforms. Avoid slingbacks, as hems can often catch in the strap, and round-toe shoes (with the exception of trainers and UGGs), which can make the overall look feel clunky rather than polished.
what shoes to wear with bootcut JEANS
The bootcut is making comeback and is another versatile style that looks good dressed up or down. Again also works brilliantly with sandals - both flat and heeled - as well as platforms.
You can, of course, wear whatever you like, but these shoe choices will help create a more balanced look. While I haven’t included sandals here, both flat and heeled styles work with pretty much all jean silhouettes.
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As a personal stylist I style women in the London area or online. Working with you to discover what truly works for you and eliminating what to wear stress for all occasions.
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Thank you for reading!
Lisa