Skip to content

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

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

Shipping toUS · $UK · £Europe · €Deutschland · €

TOMS Santiago Loafer in Navy Recycled Cotton Canvas

Santiago Loafer

by TOMS · Loafers & lace-ups

$75

Navy 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

More from TOMS

Mens Resident Plus Drizzle Grey Heritage Canvas
Mens Marcos Loafer Tan Suede
Mens Nico Sandal Dune Suede
Mens Alp FWD Grey Knit
Mens Alpargata Rope 2.0 Espadrille Dune Suede
Womens TRVL LITE Retro Runner Sneaker Water Repellent Lunar Grey Suede
Silas Forest Green Tortoise Traveler Sunglasses
Sequoia Chestnut Tortoise Handcrafted Sunglasses

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

Explore

Men's outfits with 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

Smart casual$619
Everyday$398
Smart casual$174
Smart casual$174

What to wear with it

Complete looks built around these loafers.

Brown sweater, green pleated pants & navy loafers

$619 · Pieces from $75

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

Jacket, tee & shorts

$398 · Pieces from $45

For mild days, about 55–70°F · Everyday · 5 pieces from $45

Jachs NY · $49

Jachs NY · $50

Plaid flannel, brown pants & navy loafers

$174 · Pieces from $49

For cool days, about 40–55°F · Smart casual · 3 pieces from $49

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

Jachs NY · $49

Jachs NY · $50

Plaid flannel, brown pants & navy loafers

$174 · Pieces from $49

For cool days, about 40–55°F · Smart casual · 3 pieces from $49

Flannel, olive pants & navy loafers

$193 · Pieces from $49

For cool days, about 40–55°F · Smart casual · 3 pieces from $49

Jachs NY · $40

Jachs NY · $69

Jachs NY · $50

Overshirt, brown sweater & grey pants

$234 · Pieces from $40

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

Aimé Leon Dore · $70

Blue shirt, pants & navy loafers

$321 · Pieces from $75

For warm days, about 70–85°F · Everyday · 4 pieces from $75

Thursday Boots · $120

Eddie Bauer · $80

Howler Bros · $99

Blue denim jacket, flannel & brown pants

$374 · Pieces from $75

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

Southern Marsh · $139

Everlane · $128

Eddie Bauer · $90

Represent · $110

Camo jacket, flannel & beige pants

$542 · Pieces from $75

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

Marine Layer · $150

Howler Bros · $115

Olive bomber jacket, grey flannel & pants

$409 · Pieces from $69

For cool days, about 40–55°F · Smart casual · 4 pieces from $69

How to wear the TOMS Santiago Loafer

Counted from 10 of these looks.

What goes with the TOMS Santiago Loafer

On top: Shirts or knitwear
Bottoms: Pants
Layers: Jackets

Colors that work

Navy, brown, grey and green 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 $193 and $409; the typical one is $374. 8 include a piece on sale. Swap any piece to change the total.

Brands in these looks

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