City Style

Tailoring, sneakers and the smart-casual line nobody explains properly.

GuideTobias Reed23 Sept 20265 min

Dress for the client, not for the restaurant

The room has a wine list the size of a hymnal and none of that matters. What matters is the four feet of you the client can see across the table.

Wear a Trench Coat Without Looking Like a Detective

From the City Style archive

Older stories

GuideTobias Reed22 Sept 20265 min

What tailoring actually costs and what's worth paying for

GuideTobias Reed22 Sept 20265 min

The one suit to buy when you own none

GuideTobias Reed22 Sept 20266 min

Getting to work dry when the weather turns

GuideTobias Reed22 Sept 20265 min

How to tell a trend isn't for you before you buy it

GuideTobias Reed23 Sept 20265 min

Dressing for a City Winter Without Looking Like a Tourist

GuideTobias Reed23 Sept 20265 min

Dress shoes that survive a ten thousand step day

City Style on video

Worth an hour of your evening

From channels we rate. Plays on YouTube or TikTok.

Gentleman's Gazette27 Sept

15 Little Things Only True Gentlemen Do (That Have a Big Impact)

Gentleman's Gazette20 Sept

I'm A Custom Clothier: Here Are My Favorite Jackets

Gentleman's Gazette18 Sept

50 Fabrics You Need To Know (Part 3)

Mens Fashioner28 Feb

How To Wear Black Sneakers | Men’s Shoe Style Advice | Men’s Shoes

40+ Men's Fashion21 Oct

The ONLY Smart Casual Sneakers You Need After 40 (Stop Buying the Wrong Ones!) | 40+ Men's Fashion

The Style O.G.10 Apr

Why Minimal Sneakers Are Best For Older Guys

Josh Dominic2 Feb

The Best Everyday Minimal Sneakers in Every Price Range in 2025

Gentleman's Gazette16 Apr

Smart Casual Dress Code Explained - What To Wear With Style For Men & What Not - Gentleman' Gazette

Dapper Dads30 Sept

How to Dress Smart Casual After 50 | Modern & Effortless Mens Fashion Guide

Huckberry17 Aug

How To Elevate Your Smart Casual Wardrobe | Ben’s Smart Casual Style Guide

Inspire Style26 Sept

The Ultimate Guide to Business Casual (Upgrade Your Wardrobe!)

40 Over Fashion7 Jun

Breaking Down SMART CASUAL Dress Codes | What To Wear

theDapperVault23 Jun

What Is Smart Casual? | 5 Basic Smart Casual Outfit Ideas

40+ Men's Fashion26 Jul

How to Dress for Business Casual Without Looking Outdated | 40+ Men's Fashion

Real Men Real Style13 Aug

How To Dress Casually As An Adult Man (Stop Dressing Like A Boy)

Tair Omari25 May

How to Dress Smart Casual Like a Modern CEO | Mens Fashion Guide

TikTok@luke_liu

5 ways to wear an overcoat #overcoat #coat #mensstyle #mensfashionwear #outfitinspo

TikTok@markkoob

3 different variations for styling a wool overcoat. I wanted to do a few different outfits to show day and night time looks with a overcoat. Like I said, I do think these outfits would work best with a black loafer. #stylingoutfits #overcoat #overcoatoutfit #creatorsearchinsights

TikTok@treybryantstyle

How To Style A Overcoat The Right Way

TikTok@dailysav

Don’t be most guys. It’s time to upgrade the puffer jacket and get into an overcoat. #mensfashiontips #mensfashion #winterfashion

City Style quizzes

Quiz yourself, then your friends

All quizzes

GuideTobias Reed23 Sept 20265 min

How a white shirt goes gray, and how to stop it

The collar ring isn't dirt, the yellow under the arms isn't sweat, and chlorine bleach is making both of them worse.

GuideTobias Reed23 Sept 20265 min

The Saturday wardrobe that isn't sportswear

Four swaps that get you out of the technical half-zip on days you're not training, without buying a blazer you'll wear twice.

Ask BRO

What should I wear to this?

Ask it

GuideTobias Reed23 Sept 20265 min

Match the belt to the shoe and the socks to the trousers

Two rules cover most of it. The rest is knowing when a 35mm belt is wrong, why your socks fall down, and when to break both rules on purpose.

GermProof.com — An invisible germ barrier on your skin for hours

PartnerGermProof.com

6 min read

Three straps and one watch will cover your whole year

Buy the right case size, check the lug width before anything else, and learn to change a strap without scratching the lugs.

Poll

When did you last ask for a raise?

GuideTobias Reed23 Sept 20265 min

Black tie, charity dinners and what the invitation means

Decode the line at the bottom of the card, then get the six details right that everyone in the room will notice.

GuideTobias Reed23 Sept 20265 min

How to stay sharp when the city hits thirty degrees

Heat doesn't just make you uncomfortable, it makes you slow and short-tempered. Shift your day and your kit before it does.

Names.com — The name is the first thing you sell

PartnerNames.com

GuideTobias Reed23 Sept 20265 min

What to wear to an interview at a company with no dress code

"Come as you are" isn't an instruction. It's an unwritten code, and you can read it in about ten minutes.

Quiz

Is your money actually in order?

Six questions. No email required, no sales pitch at the end.

GuideTobias Reed23 Sept 20265 min

Four days of meetings out of one carry-on

Pick the shoe first and the rest of the trip packs itself. What to take, what to leave, and where the plan falls apart.

GuideTobias Reed23 Sept 20266 min

Most men need one tie knot, not five

The four-in-hand covers almost everything, the width matters more than the pattern, and there are days when the tie makes you look worse.

Ask BRO

Rewrite my CV so it actually gets read

Ask it

GuideTobias Reed23 Sept 20265 min

Dry clean less, brush more, and the suit lasts years

A clothes brush, a proper hanger and a day off between wears will keep a suit sharper than any dry cleaner, and cost you about two minutes a day.

Coconut.com — Tell us when. We find where the sun is.

PartnerCoconut.com

GuideTobias Reed23 Sept 20265 min

The sale rack only rewards people who came with a list

Second markdowns, final-sale traps, and the one question that kills a bad buy before you get anywhere near the register.

Poll

Where does your phone charge overnight?

GuideTobias Reed23 Sept 20265 min

Oxfords, derbies and loafers, and when to wear each

The difference is in the lacing, and it decides everything else. What to wear to a funeral, an interview, a wedding in August and a Tuesday at the office.