Vintage Americana headwear

Caps & hats, made the old way.

Herringbone flat caps, genuine-leather newsboys and wool fedoras — honest materials in shapes that never date.

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Genuine leather newsboy cap at Westside Boot & Shoe
Fedora & brim

Brims with real backbone.

Wool felt, suede and leather — fedoras, porkpies and trilbies shaped to hold their form season after season.

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Genuine leather suede fedora hat
Everyday caps

Broken-in from day one.

Washed cotton ball caps, snapbacks and truckers — the easy rotation you'll reach for every morning.

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Washed cotton baseball cap
Free U.S. shipping $50+$4.95 flat on orders under $50
Ships in 1–2 business days3–7 business days in transit
30-day returnsBuyer pays return postage
Shipped from the USAEst. in the USA
About Westside Boot & Shoe
Why Westside

Headwear built the old way

From herringbone flat caps to genuine-leather newsboys, wool fedoras to broken-in ball caps — Westside Boot and Shoe stocks headwear made from honest materials, cut in classic shapes that never date.

Every order is packed and shipped from the USA, usually within one to two business days.

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Customer reviews

Don't take our word for it

Read verified customer reviews of Westside Boot & Shoe on Trustpilot — the good and the honest.

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Talk to us

Questions about sizing or an order?

A real person reads every email — usually answered the same business day.

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Good to know

Frequently asked questions

Shipping is free on U.S. orders of $50 or more. Orders under $50 ship for a flat $4.95. We currently ship to U.S. addresses only. Full details on our Shipping Policy.

Orders are packed within 1–2 business days. Once shipped, delivery normally takes another 3–7 business days, and you'll get a tracking link by email.

Measure around your head just above the ears with a soft tape. Each product page lists that style's size range in both centimeters and inches — match your measurement to the closest size. Between sizes? Go up.

Yes. You have 30 days from delivery to return any unworn item with tags in its original packaging. Return postage is paid by the buyer, unless the item arrived damaged, wrong, or never arrived. Refunds go to the original payment method within 5–10 business days. See our Refund Policy.

Email support@westsidebootandshoe.com with your order number and a photo. If a parcel is damaged, wrong, or doesn't turn up, we replace it or refund you in full — and we cover return postage in those cases.

Email support@westsidebootandshoe.com or use our contact form. A real person reads every message, Mon–Fri, 9 AM – 5 PM MT — usually answered the same business day.

Still stuck? Send us a message and we'll help.
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New styles, first look

Restocks and new arrivals land in small batches. The list hears first.