Sep 28, 20263 min read

The 5 Shoes Every Man Needs (and Chelsea vs Oxford vs Loafer)

By Oswin Hyde · Last updated 28 September 2026

The short answer: five pairs cover almost every occasion: black Oxfords for formal events, brown Derbies or brogues for the office and smart-casual, a dark brown leather Chelsea boot for autumn and winter, loafers for spring and summer, and white leather trainers for weekends. If you can only buy one pair, choose dark brown leather Chelsea boots or brown Derbies; they work with suits, chinos and jeans.

The 5 shoes every man needs

#	Shoe	Why	Try
1	Black Oxfords	Weddings, interviews, funerals, black tie at a pinch	Wilson Black, Dean Black
2	Brown Derbies or brogues	The everyday office and smart-casual shoe	Miller Brown, George Brown
3	Dark brown Chelsea boots	Autumn and winter; suits, chinos and jeans	Christopher Brown, Darwin Brown Suede
4	Loafers	Spring, summer and relaxed tailoring	Wyatt Tan, Morgan Brown suede
5	White leather trainers	Weekends and relaxed offices	Harper White

Chelsea boots vs Oxfords vs loafers: which should you buy?

	Chelsea boots	Oxfords	Loafers
Formality	Smart-casual to smart	Most formal	Smart-casual
With a suit	Yes, sleek black or dark brown	Yes: the classic choice	Yes, especially in summer
With jeans	Yes	Brown or suede only	Yes
Season	Autumn and winter	All year	Spring and summer
Ease	Pull on	Laces	Slip on
Best if	You want one versatile pair	You need formal shoes	You want relaxed and smart

Choose Oxfords if you wear suits often or have formal events coming up. Choose Chelsea boots if you want one pair that works across the office, evenings and weekends. Choose loafers if your wardrobe is mostly chinos and relaxed tailoring. More detail in our guides to Oxford shoes, Chelsea boots and loafers.

Oxford vs Derby

Oxfords have closed lacing and look sleeker; Derbies have open lacing, suit a higher instep and are a little more relaxed. For an office that has moved to smart-casual, a brown Derby is often the more useful shoe. See brogues, Derbies and monk straps explained.

Which colours first?

Start with black for formal and brown for everything else, then add tan or suede. Our shoe colour guide shows which colour goes with which suit.

What makes a good leather shoe?

Full-grain leather that creases softly and takes polish.
A leather lining that breathes.
A padded insole and a heel that grips.
The right size and width: see our shoe size guide.

All Oswin Hyde shoes use 100% full-grain crust leather from LWG Silver-rated tanneries, with lambskin or sheepskin linings and padded insoles. See how our shoes are made.

Frequently asked questions

What shoes should every man own?

Black Oxfords, brown Derbies or brogues, dark brown Chelsea boots, loafers and white leather trainers.

If I can only buy one pair of shoes, what should it be?

Dark brown leather Chelsea boots or brown Derbies: both work with suits, chinos and jeans.

Are Chelsea boots better than Oxfords?

They are more versatile but less formal. Choose Oxfords for weddings, interviews and conservative offices.

Loafers or Oxfords?

Oxfords are more formal; loafers are more relaxed and suit spring, summer and smart-casual offices.

What are the best leather shoes for men?

Full-grain leather shoes with a leather lining, a padded insole and the right fit for your foot.

Shop the pieces in this guide: all shoes · Oxford shoes · Chelsea boots · loafers · trainers

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