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Discover Search

New looks, once a week

A few complete outfits picked from what's new. No account needed, unsubscribe any time.

Email address

Outfit ideas Brands Gift guides Black Friday deals Thanksgiving outfits Holiday party outfits What to wear with white sneakers Women's date night outfits Men's work outfits Fall outfits Winter outfits Streetwear outfits Minimalist outfits Women's workout outfits Men's smart casual outfits Outfits under $100 Outfits under $200

Wholefit is an independent outfit recommendation site. It isn't affiliated with or endorsed by the brands it shows, and you buy each piece on the site of the store that sells it. No store or brand pays us a commission yet; when one does, it won't decide what we recommend.

About Outfit study Privacy Policy Your Privacy Choices Terms of Use Affiliate Disclosure Brands & Copyright Accessibility Contact

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TOMS Santiago Loafer in Black Recycled Cotton Canvas

Santiago Loafer

by TOMS · Loafers & lace-ups

$75

Black Recycled Cotton Canvas

Size

Would you wear this?

Shipping $8.99 · 30-day returns, fee applies PolicyFrom TOMS' own policy and checkout, checked 2026-10-19. The store's checkout has the final word.

No brand pays Wholefit a commission yet. How we earn

Ways to wear it

Details

Removable custom CloudBound™ foam insoles
Rope-wrapped midsole
Collapsible heel construction

Material: Recycled cotton canvas

As listed by TOMS. Check the product page for anything not shown here.

Tailored Workwear

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Womens Alpargata Plus Brown Sugar Leopard Print Suede
Womens Marie Loafer Natural Textile
Womens Marie Loafer Black Textile

What to wear with the TOMS Santiago Loafer Black Recycled Cotton Canvas

Explore

Men's outfits with loafers
Men's outfits with black loafers
Men's outfits under $100
Men's outfits under $150
Men's outfits under $200
Men's outfits under $300
Men's workwear outfits
Men's tailored outfits
How to style TOMS

TOMS Santiago Loafer, photo 2

TOMS Santiago Loafer, photo 3

TOMS Santiago Loafer, photo 4

TOMS Santiago Loafer, photo 5

Ways to wear it

Everyday$583
Everyday$610
Smart casual$323
Smart casual$1,400

What to wear with it

Complete looks built around these loafers.

Buck Mason · $248

Buck Mason · $62

Buck Mason · $198

Brown jacket, cream tee & jeans

$583 · Pieces from $62

For cool days, about 40–55°F · Everyday · 4 pieces from $62

Stüssy · $195

Stüssy · $160

Black denim jacket, leopard top & white jeans

$610 · Pieces from $75

For cool days, about 40–55°F · Everyday · 5 pieces from $75

Howler Bros · $129

Howler Bros · $119

Black shirt, olive corduroy pants & black loafers

$323 · Pieces from $75

For cool days, about 40–55°F · Smart casual · 3 pieces from $75

Would you wear these?

Yes or no on a few looks, and the feed learns what to show you.

Start, about a minute

Your taste

A feed of looks picked for you

Stüssy · $325

Stüssy · $725

Stüssy · $275

Black trench coat, white shirt & striped pants

$1,400 · Pieces from $75

For cool days, about 40–55°F · Smart casual · 4 pieces from $75

tentree · $218

tentree · $118

Black jacket, green sweater & brown pants

$489 · Pieces from $75

For cool days, about 40–55°F · Smart casual · 4 pieces from $75

Southern Marsh · $70

Southern Marsh · $89

Green flannel, khaki pants & black loafers

$234 · Pieces from $70

For cool days, about 40–55°F · Smart casual · 3 pieces from $70

Olive vest, black flannel & pants

$475 · Pieces from $69

For cool days, about 40–55°F · Smart casual · 5 pieces from $69

Howler Bros · $115

Howler Bros · $119

Orange shirt, charcoal corduroy pants & black loafers

$309 · Pieces from $75

For mild days, about 55–70°F · Smart casual · 3 pieces from $75

Eddie Bauer · $90

Howler Bros · $89

Blue flannel, tan pants & black loafers

$254 · Pieces from $75

For cool days, about 40–55°F · Smart casual · 3 pieces from $75

Duck Camp · $109

Shirt, pants & black loafers

$259 · Pieces from $75

For mild days, about 55–70°F · Smart casual · 3 pieces from $75

How to wear the TOMS Santiago Loafer

Counted from 10 of these looks.

What goes with the TOMS Santiago Loafer

On top: Shirts or t-shirts & tops
Bottoms: Pants or jeans
Layers: Jackets

Colors that work

Black, brown, green and cream come up most often across these looks, so they make an easy base to build on.

What a complete look costs

Most whole outfits here cost between $259 and $583; the typical one is $475. 5 include a piece on sale. Swap any piece to change the total.

Brands in these looks

Most pieces come from TOMS, Howler Bros, Stüssy and Brixton. Each look checks out on the stores' own sites, one store at a time.