North by Northwest is my all-time favorite movie.
Cary Grant’s classic look may have prompted my shameful self-tanner phase in high school, but it also gave me my present-day go-to work look: The gray suit.
Specifically, the gray suit with brown shoes.
Yes, there are more rules with this combo than a gray suit with black shoes or an all-black situation, but gray suits have come a long way from symbolizing post-war conformity. Today they’re distinctive.
When paired with brown shoes, gray is almost bold, but not loud.
The gray suit brown shoes playbook is easier than you think. We’ll show you.
Why is a Gray Suit a Worthwhile Investment?
The gray suit always works. It’s like an Amex Centurion—it won’t get declined.
Black is the most formal and navy is the power color. Gray used to symbolize submissiveness, but today it represents reliability. It’s an effective look whether you’re the boss or an intern.
It’s the suit that you’ll have the most opportunities to wear. Even on the shade spectrum, light gray is the most versatile of the light colors, and dark gray is the most approachable of the dark colors.
What Makes Gray and Brown a Great Combination?
Opposites attract. Gray is cool and brown is warm. There are warmer and cooler tints of each, but their core temperatures are incorruptible.
Secondly, they’re both neutral colors, so all gray-brown pairings are subtle and grown-up.
Finally, you see them combined in nature all the time: Chic marble, rugged tree trunks, epic mountains, and downy feathers. The pairing is literally natural, so even the boldest combinations are never jarring.
6 Simple Tips for Matching a Gray Suit With Brown Shoes
Choose the Right Gray Suit Color
Despite the racy novels your girlfriend read as a teenager, there are actually far more shades of gray than 50. Don’t let this overwhelm you.
As a foundation to build from, let’s talk seasons.
The quick-and-dirty is lighter colors in warm seasons, darker colors in cooler seasons. Cool undertones for summer and winter, warm undertones for autumn and spring.
In early spring, wear a light charcoal suit. You’ll have been wearing darker colors in the cold seasons, so this is a subtle transition. Wearing gray is all about subtlety. During warmer spring days approaching summer, opt for stone gray which has a khaki undertone.
For summer, wear a cool, light gray.
In the beginning of fall, wear brownish hues like pewter gray. Towards the end of fall, go darker with medium grays like taupe.
For winter, charcoal is your friend in most settings.
If you’re feeling festive, you can also go for a dove gray. Its pink undertones make it perfect for the holidays!
For formal occasions, wear darker grays and for casual events, wear lighter grays. Darker suits at night, lighter suits during the day.
I know this sounds like a lot of moving parts, but if you follow at least one principle, often all or most of the others automatically follow suit.
For example, summer garden parties are usually a day event. For an occasion like this, wear a seasonal cool, light gray and you’ll notice that you’re also checking off the boxes for proper day attire and proper smart-casual attire.
While formal New Year’s Eve parties can certainly last until morning, they always start at night. Opting for charcoal grey will similarly check all the appropriate boxes.
Thinner pinstripes are an understated look, thicker pinstripes are more statement, and chalk stripes strike a balance.
Save pinstripes for work or cocktails and avoid them for anything very formal and very casual. There shouldn’t be a single pinstriped suit at a black-tie benefit or a club opening.
Select a Complementary Brown Shoe Color
Choose a darker shade of brown for your shoes than your gray suit. The darker the shoe, the more formal it is.
If you want to up the volume on boldness, choose warmer browns for the cooler grays and vice versa.
Here are suggestions based on those guidelines, from lightest gray to darkest:
- For light gray suits, choose tan, cognac or honey brown for your shoes
- For light charcoal or stone gray, choose standard medium or dark brown for an all-around neutrality
- For pewter gray and taupe, go for standard dark brown or mahogany
- For charcoal, choose burgundy for a bolder look and standard dark brown for a neutral, understated look
Match Your Shoe Style to Your Purpose
The fundamental rule for shoe style (other than buy what you love) is to match it to your purpose.
Certain boots live in both casual and smart-casual worlds. For example, Chelsea boots go well at no-tie occasions and at professional happy hours. The M.Gemi Dritto works very well with its Italian flare:
Nice sneakers can be worn successfully with a gray suit in select no-tie situations. Just make sure they’re high-end, chic, and clean. Think Thom Browne, patron saint to the cool guy.
Boat shoes enter the game if any of the above scenarios are by the water, at a beach club, or of course, on the beach.
Finally, dress shoes work in most, if not all, suit events. It’s a suit, after all.
Pick the Right Shirt
Don’t get too caught up with the minutiae of classic collars. English spread, spread and forward point collars all hold a tie perfectly in place.
Abbreviated spreads are for tieless looks only.
Button-down oxford collars are good with or without ties. They, along with club collars, add an Ivy League flare. Note: Laying this look on too thick, say with cable-knit and a club tie, may prompt purists to qualify you with casual questions about your background (Read: Your pedigree).
If you love the look though, just ignore all of that and wear what makes you feel good!
Lighter shirts like chambray and linen are for casual or summer scenarios and work well with light gray more than any other color, in my opinion. They strike a balance of dapper and approachable, that’s too casual for black suits and too party-time for white suits.
Check patterns are versatile. Just make sure shirt patterns are bigger than tie patterns.
Nicer dress shirts, like herring bone and fine striped shirts, can really travel through the gray suit universe.
They elevate lighter, softer gray suits and perfectly match darker heavier gray suits.
Blue, light blue, and white shirts go with gray 100% of the time because of the tasteful, subtle contrast.
Black shirts, and other very dark colors, will make even the lightest gray look formal and sharp.
White, black, grey and navy turtlenecks go great with winter grays. Deep reds, greens and browns go great with autumn grays.
Pinks, yellows, and pastels should be reserved for three settings: Light-hearted situations, summer, and when you’re purposely making a statement.
Never Forget the Importance of Fit
Know your body type. Be mindful that your body type at 25, 35, and at 65 may not be the same so keep track of yourself. Gray doesn’t hide everything the way black can, so fit is of the utmost importance.
Thin men can pull off a slim-fit or even a skinny-fit without looking too rock n’ roll.
If you’re thin but never miss leg day (looking at you, Lionel Messi), stick to a slim-fit over a skinny-fit to avoid too much snugness in the thighs.
Shorter thin men should choose slim-fit over skinny as well. The bottoms of skinny pants don’t touch your shoes, whereas slim-fit pants just graze them, which adds height.
Gray always looks good in regular-cuts, likely because we immediately connect it with 60’s Hollywood leading men. This look is flattering on most men except for the most thin. It can make you look like a child who raided dad’s closet.
The regular-cut looks exceptionally noble on bigger men. Pour Homer Simpson into a classic, regular cut, and he’ll come out looking like Downton Abbey’s Lord Grantham.
Some think men over 50 should stick to regular cuts, but I think body-type is more important than age.
Classic regular-cuts are often associated with higher end fabrics. I love a slim-cut with nice fabrics, but the logic here is you should only spend a premium on suits that won’t go out of style.
Accessories Are Your Friend
Have fun with your tie.
Hardly groundbreaking advice, but the gray suit is such a neutral palette that design features like stripes and chevrons are less risky. Patterns on your tie should be smaller than patterns on your shirt.
A very general rule is that your tie should be darker than your shirt, especially with a gray suit.
If the tie is washed-out, you may as well not wear one. The exception to this rule is with black and very dark shirts. In a formal scenario, the safest bet with a black shirt-gray suit combo is a white tie or a tie that matches the suit.
Match your belt and briefcase to your shoes. Match your socks to your pants for a professional look and to your tie for a fashion-forward look.
Don’t match your pocket square to your tie. This is as important as not buttoning the bottom button of your two-button jacket.
If your tie is solid, wear a white, black, or gray pocket square or match it to a secondary color on your shirt or the hue of your suit. If your tie is patterned, you can match your pocket square to a secondary or tertiary color in the tie.
The pocket square accentuates the outfit. It’s not a color block.
Suit Up, Soldier
Sporting light grays and cool browns are indeed best at beach parties, and rocking dark grays and burgandys are best for formal dinners. These simple guidelines make it easy for anyone to look classic but distinct, and yet there’s enough room within them for experimenters to have fun!
We can’t all be Cary Grant, but following just a couple best practices when combining a gray suit with brown shoes can make even a fashion newbie look like he knows what he’s doing.
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How should I style a gray suit with brown shoes for a wedding?
For a formal white-tie wedding, you can wear a dark black shirt so that the tie stands out, and vice versa for a black-tie wedding. Style the look with all or some of the following: A tie-clip, cufflinks and a dress watch with either a precious metal strap or a leather strap that matches your burgundy shoes.
For more casual, outdoor weddings during the warm seasons, the no-socks look paired with one upscale accessory like a classic watch makes the put-together look seem effortless.
Pastels are good to go for beach weddings too. Weddings come in so many shapes and sizes these days and fortunately the gray-brown pairing is incredibly versatile. Consider the venue (indoor, outdoor, church, hotel, etc), the season, whether or not there’s a theme and dress-code, and finally, do not outdress the groom.