Navy Sports coat – A staple in any man’s wardrobe, this will always be an extremely versatile piece. Transitioning effortlessly from being paired with a tie and slacks in the office to jeans and a sport shirt for a night out, a solid navy sports coat is always appropriate. It goes with everything you already have in your wardrobe, providing a large amount of utility to any guy. Try grabbing one with a little bit of texture and you’ll be good to go just about anywhere. Pictured: Rafaelle Caruso

 

Charcoal Slacks – If you’re only going to have one pair of slacks, a rich charcoal is definitely the way to go. They will act as a neutral that can be paired with everything save for a coat of the same color. If you opt for a slightly trimmer option, they’re also appropriate outside of work for a smart casual look that is timeless. Worsted wools and twills will be inherently dressier, but something like a tic weave or the textured pair above make great transitional pieces. Pictured: Incotex

 

 

Brown Dress Shoes – Being able to be worn with everything but a tuxedo, a sleek brown shoe should be every guy’s go-to option. If you need something more formal, go for an oxford captoe and be ready for that interview. A blucher would then be the more casual option to pair with jeans, and a wingtip balmoral treads the middle ground, being able to go either way. Try to stay away from squared toes, pointy toes, or overly round lasts that don’t give the foot any definition. Pictured: Edward Green

 

Cotton Chinos – The iconic “khaki”, has evolved over the years, and has settled on a trim, but not skinny, fit. While you can find them in almost any color, deep tan and stone are easiest to pair with the rest of your wardrobe. A great pair of chinos can be worn casually with something as simple as a v-neck t-shirt and still easily transition to a blazer and a striped tie. To avoid excess wrinkles and attain a cleaner look, make sure there is only a slight break and that there is no stacking of fabric above the shoe. Picture: Incotex

 

Dress Shirt – No matter what your personal style is, a simple white dress shirt is always classic choice. Light blue ties for first place, but white will go with literally any combination of jacket and tie because it serves as a blank canvas. Choose one with a collar that compliments the shape of your face well (a medium spread works for most), and save the button down for your second shirt, being that is typically a more casual option. Also, a subtle herringbone or twill weave adds texture and interest to an otherwise basic shirt. Pictured: Eton

 

Boots – Serving as your go-to shoe for casual affairs, these will be for any time your brown lace-ups would be overkill. For the spring and summer months, pair these with a great pair of denim or even your casual chinos. During fall and winter, they also look perfectly at home with some flannel trousers and a tweed sport coat, giving off that British countryside vibe. The great thing about an awesome pair of brown boots is the patina they will develop with age – they’ll continue to look better the more you wear them! Pictured: Wolverine 1,000 Mile Boot

 

Charcoal Suit: For a go-to, classic and versatile suit, a deep charcoal is your best bet. Navy works just as well, but if you’re only going to have one, a charcoal will serve as nice addition to your navy blazer. With so many options to choose from, it’s usually best to stick with the basics. Go for a 2 button closure with notch lapels, double vents, and flat front trousers. If budget allows, opting for a fully canvassed jacket with classic styling will allow you to look appropriate for years to come. Pictured: Samuelsohn

 

White Linen Pocket Square – Throw this in any jacket for every occasion. Folded over neatly and squared off on top, it should have roughly half an inch showing and take up the full width of the breast pocket. Patterned silks in fun colors can also finish off an outfit well, but nothing has that same timeless look as a simple white linen one. Don’t be afraid of not having it match, because part of the beauty of the pocket square is the subtle flow it brings to an ensemble without trying to have it act as a center piece. Pictured: Private Label

 

Dark Denim – Leave those “dad” jeans at home, its time to bring out what guys should have been wearing all along. A pair of solid, dark blue denim is an amazingly transitional wardrobe staple for any occasion less formal than conservative business dress. Dark is they key word here, because anything lighter and their ability to be worn dressed up flies out the window. Make sure that they stay trim, not skinny, and don’t be afraid to rock them with a cool casual sport coat and a club tie if you’re feeling a bit preppy. Pictured: Levi’s Made & Crafted

 

Leather Jacket – We’re not talking about those 50lb biker jackets here, but rather the sleek alternative. A dark brown leather jacket in an ultra lightweight lambskin not only feels amazing, but it allows for an added option of versatility in your wardrobe. Of course it can be worn as a layering piece over your outfit for when it’s a bit chilly out, but try also using it as a more casual version of a sports coat for a night out. Even if paired with a more casual textured tie, it can do well to bridge that gap between casual and dressed. Pictured: Gimo’s

 

V-Neck Sweater: Depending on the weight, this piece can be used both for it’s added warmth during the cooler months as well as a great way to add color and texture to a spring or summer ensemble. Being the most classic sweater type, it’s always appropriate. Cashmeres are quite easy to find, and normally provide the most warmth out of the commonly used fabrics for v-necks. On the other hand, cottons are perfect for the spring and summer months, offering a high amount of breathability and comfort. Pictured: Seletti

 

Fun Socks: While they’ve become very popular in recent years, the sartorially adventurous gentleman has always found an occasion to don a pair of whimsical socks. They don’t have to be over the top loud, but because they are rarely seen, it’s nice to sometimes add a splash of color or a cool pattern to an otherwise sober outfit. Wear whatever color or pattern suits your mood, and don’t try to match them to the rest of your outfit. Merino wool over-the-calf versions are great at whisking away moisture and maintaining their shape throughout the day. Pictured: Marcoliani

 

1/4 Zip Sweater: Being the sportier alternative to a v-neck, the 1/4 zip sweater is at home for those less formal occasions. Extending low enough to show a tie, these sweaters can act as a buffer between dressy and casual, and actually allow for a lot of play when it comes to patterns and textures. Try throwing one over your favorite sport shirt and finish it off with a casual jacket and denim for a great look that’s put together, yet fun and versatile. Lightweight merino wool makes a great year-round fabric, enabling you to easily layer. Pictured: Brioni

 

Outerwear Jacket: The specification of this particular piece will vary depending on your location, but every guy needs something to wear for when it’s wet out. Cashmere overcoats work well for the cold, but are not something you would normally wear during a rainstorm. For that reason, a lightweight waterproof jacket is a great piece to wear over whatever your normal outfit would be for the day. Avoid the ankle-length versions and instead opt for something that sits about mid thigh, protecting the entirety of you upper body and then some. Pictured: Luciano Barbera

 

Silk Tie: Even if not required by work, there will always be occasions in your life that will require a necktie. Everyone’s taste is different, but versatility is something that a tie should add to your wardrobe. Instead of pairing that one shirt with that one tie, try grabbing a tie that can work with a variety of outfits.  A solid navy in a gabardine or knit is one of the easiest types to wear; try it some time and see what it won’t work with! Also, a repp stripe with hues of burgundy or navy will always be a staple. Pictured: Brioni

 

Sport Shirt: Whether it’s time for that easy casual weekend or a fun night out, a sport shirt serves as a way to look great without being overdressed. Normally shorter and trimmer than dress shirts so they can also be worn untucked (only rarely, though!), a casual shirt looks at home with the sleeves rolled up and paired with some chinos or jeans. A colored check usually works best, and having a button down collar helps solidify its away-from-the-office vibe. The right type can also work well under an unlined, casual sports coat. Pictured: Luciano Barbera

 

Casual Sports Coat: Having a piece like this ensures that you will always have something to throw on for any occasion. Rather than a solid worsted wool, a sports coat with a bit of pattern and texture allows for it to be used in a plethora of situations ranging from downtown strolls, to date night, and even to the office. Try one with a more deconstructed approach and softer shoulders, thereby making  it both more comfortable, and less stuffy for non-work related endeavors. Cotton/linen blends work well for the summer, and tweeds are always appropriate for the colder months. Pictured: Canali

 

Belts: The rule is to normally match the color of the belt to your shoes, and that advice is always a safe bet. However, when not dressing in a conservative business environment, it can be fun to stray from the beaten path. As long as your belt and shoes aren’t at odds with one another (black paired with brown, for instance), you can throw a little bit of unusual color into the mix or even play with complimentary shades of the same color, or even pastels if you’re feeling daring. Simple calfskin is the most obvious choice, but implementing an alligator or even ostrich belt into your rotation is an easy way to stir things up. Pictured: W. Kleinberg

 

Colored T-Shirts: While a white undershirt will always have it’s place, swapping in one with a bit of color is a great way to add some character to a casual, tieless look. For instance, throwing a burgundy t-shirt under a sport shirt that has a hint of red to it can bring out the undertones and completely change the overall look. They can also be worn alone with a pair of casual pants on a warm day, just make sure that the details are finished off well. Pima cotton is normally the best choice, and provides a wonderful balance of comfort and breathability. Pictured: Left Coast T

Scarf: Yes, a solid cashmere scarf is a staple for any guy, but what about the warmer months? Most guys forget that a lightweight scarf during the hotter months can add a bit of whimsical fun, but also protect against the sun. Cashmere fights the cold, linen fights the sun, and lightweight wool transitions between both. A scarf not only serves as protection, but also enables yet another way for a man to implement texture or pattern into an otherwise conservative outfit. Casual or dressed, the right scarf will always have its place. Pictured: Sand

(Wolverine 1,000 Mile Boot in brown)