The Easy and Hard Part of Classic Dress
Every once in a while, you’ll see a new member on StyleForum say that he’s just become interested in classic, tailored clothing, and would like to know what he should buy. This is always a difficult question to answer, as so much depends on the region and profession you’re in. Someone in the tech sector in the Bay Area, for example, will have very different needs than someone in finance in New York City.
However, to the extent that some advice can be given, the basics of a classic wardrobe are remarkably straightforward.
Pants and Shirts
First, buy a bunch of wool trousers in various shades of gray, from light to medium, and maybe throw in one or two pairs in brown for good measure (again, light to medium shades work best). Flannel wool and some kind of wool twill are great starters. The first will feel better, but the second will be harder wearing. You can supplement these with a couple of seasonal trousers, such as tan linens for summer and cavalry twills for fall, as well some year-round casual basics such as khaki chinos and dark blue jeans (most of these being your weekend pants, although chinos work pretty well as office wear these days).
For your shirts, focus on light blues. Solids are a good foundation, although I recommend leaning towards slightly more interesting weaves than poplin. After that, you can get a range of stripes (from thin to bold, but try to stick with in blue), as well as one or two checks (tattersalls, gingham, or graph check). Throw in a few solid white shirts as well. These will work better with more formal ensembles and for nighttime activities. Since you need something to wear with your jeans, I recommend some plain ol’ t-shirts in solid white or heathered grey.
Coats and TIes
Turning to sport coats, aim for simple, basic designs in navy and brown. These should have some kind of texture to them, as anything too smooth or fine will look too much like a suit jacket. A navy or brown sport coat – in a solid or conservative pattern – can be worn multiple times a week without anyone remembering when you wore it last. Take care too that your jackets don’t have any extreme details. Overly high gorges and short lengths are very in fashion right now, but these might make you look dated in a few years’ time.
If you need ties, buy repp stripes if you mostly wear sport coats, and ones with small repeating floral or figured patterns if you wear suits. I talked about both here. If you wear patterned shirts often, consider relying more on solid ties with a slightly textured weave to them. These will give your combination some interest without forcing you to think too much about whether or not what you’re wearing is clashing. Avoid anything too skinny or wide. Three and a quarter inches will suit almost anyone’s build, and should generally be in the range of your lapel width (no skinny ties with wide lapels, or vice versa). Stick to dark colors such as navy, dark green, dark brown, and burgundy for the most versatility.  
Knitwear and Shoes
For sweaters, get a couple of plain v-necks if you plan to wear them underneath sport coats. Colors such as solid navy, brown, grey, and burgundy work well. If you plan to wear your sweaters more casually (that is, without a sport coat), I recommend picking something a bit more textured or patterned to make things interesting. Arans, Fair Isles, cable knits, and buttoned mock necks are just a few of the ones I like.  You can even layer them on weekends with outerwear like this.
Finally, for shoes, I recommend these seven. 
Everything Else
Of course, these are just guidelines, and you should choose things that are right for your lifestyle and sense of taste. If you want a pair of double monks, by all means get a pair. But don’t go out and splurge on eight of them, especially if you’re just starting out. Build a foundation of classic, versatile basics, and let your taste and sense of dress mature before you buy wilder things. If you have a closet full of pin dot cutaway collar shirts, blackwatch tartan pants, and double monks in every animal skin you could find, you’re headed for a purge in a maybe a year’s time.
While you’re acquiring all these things, learn how clothes should fit. These guides should help. Also, find a good alterations tailor while you’re at it. Whether you shop at Land’s End or Loro Piana, a good alterations tailor will make your clothes look twice as good and three times as expensive.
But all this is the easy part. The hard part is in knowing how to wear your clothes well. That comes with a lot of practice and finding things that best suit your needs and personality. 

The Easy and Hard Part of Classic Dress

Every once in a while, you’ll see a new member on StyleForum say that he’s just become interested in classic, tailored clothing, and would like to know what he should buy. This is always a difficult question to answer, as so much depends on the region and profession you’re in. Someone in the tech sector in the Bay Area, for example, will have very different needs than someone in finance in New York City.

However, to the extent that some advice can be given, the basics of a classic wardrobe are remarkably straightforward.

Pants and Shirts

First, buy a bunch of wool trousers in various shades of gray, from light to medium, and maybe throw in one or two pairs in brown for good measure (again, light to medium shades work best). Flannel wool and some kind of wool twill are great starters. The first will feel better, but the second will be harder wearing. You can supplement these with a couple of seasonal trousers, such as tan linens for summer and cavalry twills for fall, as well some year-round casual basics such as khaki chinos and dark blue jeans (most of these being your weekend pants, although chinos work pretty well as office wear these days).

For your shirts, focus on light blues. Solids are a good foundation, although I recommend leaning towards slightly more interesting weaves than poplin. After that, you can get a range of stripes (from thin to bold, but try to stick with in blue), as well as one or two checks (tattersalls, gingham, or graph check). Throw in a few solid white shirts as well. These will work better with more formal ensembles and for nighttime activities. Since you need something to wear with your jeans, I recommend some plain ol’ t-shirts in solid white or heathered grey.

Coats and TIes

Turning to sport coats, aim for simple, basic designs in navy and brown. These should have some kind of texture to them, as anything too smooth or fine will look too much like a suit jacket. A navy or brown sport coat – in a solid or conservative pattern – can be worn multiple times a week without anyone remembering when you wore it last. Take care too that your jackets don’t have any extreme details. Overly high gorges and short lengths are very in fashion right now, but these might make you look dated in a few years’ time.

If you need ties, buy repp stripes if you mostly wear sport coats, and ones with small repeating floral or figured patterns if you wear suits. I talked about both here. If you wear patterned shirts often, consider relying more on solid ties with a slightly textured weave to them. These will give your combination some interest without forcing you to think too much about whether or not what you’re wearing is clashing. Avoid anything too skinny or wide. Three and a quarter inches will suit almost anyone’s build, and should generally be in the range of your lapel width (no skinny ties with wide lapels, or vice versa). Stick to dark colors such as navy, dark green, dark brown, and burgundy for the most versatility.  

Knitwear and Shoes

For sweaters, get a couple of plain v-necks if you plan to wear them underneath sport coats. Colors such as solid navy, brown, grey, and burgundy work well. If you plan to wear your sweaters more casually (that is, without a sport coat), I recommend picking something a bit more textured or patterned to make things interesting. Arans, Fair Isles, cable knits, and buttoned mock necks are just a few of the ones I like.  You can even layer them on weekends with outerwear like this.

Finally, for shoes, I recommend these seven

Everything Else

Of course, these are just guidelines, and you should choose things that are right for your lifestyle and sense of taste. If you want a pair of double monks, by all means get a pair. But don’t go out and splurge on eight of them, especially if you’re just starting out. Build a foundation of classic, versatile basics, and let your taste and sense of dress mature before you buy wilder things. If you have a closet full of pin dot cutaway collar shirts, blackwatch tartan pants, and double monks in every animal skin you could find, you’re headed for a purge in a maybe a year’s time.

While you’re acquiring all these things, learn how clothes should fit. These guides should help. Also, find a good alterations tailor while you’re at it. Whether you shop at Land’s End or Loro Piana, a good alterations tailor will make your clothes look twice as good and three times as expensive.

But all this is the easy part. The hard part is in knowing how to wear your clothes well. That comes with a lot of practice and finding things that best suit your needs and personality. 

Don’t Shop Aimlessly; Have a Plan
If I could only give three pieces of advice to a budding clothing enthusiast, they would be: find a good alterations tailor; learn how clothes should fit; and set a plan for your purchases.
I can’t stress the last point enough. Having a plan means that you’ll be more likely to build a wardrobe of versatile clothes that easily combine into outfits, rather than just a collection of various things that happen to have caught your eye. To set a plan, begin by determining your annual clothing budget. Once you’ve figured out what you can afford, allocate between half and to three-quarters of your budget to shoes, suits, sport coats, and outerwear. These tend to have the biggest ticket prices, but also the highest pay offs. You can easily look great with an excellent sport coat or jacket, even if you’re just wearing it with a mediocre button-up shirt and cheap pair of chinos.
The rest of your budget should be spread between trousers and shirts, and maybe a small amount allocated to sweaters and accessories. 
Now go through your wardrobe and figure out what holes need to be filled and what basics need to be replaced. As much as you can, try to cut your wish list in half and double the budget allocated for each item. You’ll always be happier with a small wardrobe filled with higher quality pieces than you will with a large one filled with half-neglected cheap items.
It’s too much to expect that each person out there has the same clothing needs as I do, but if I had to make a recommendation, I would say you should try to acquire two or three pairs of shoes a year, maybe the same in outerwear, and perhaps one or two sport coats or suits per season, depending on your lifestyle. This, in addition to what you’ll purchase in shirts and trousers, should put you on track to building a respectable wardrobe in about three to five years’ time. 
I update my list constantly, and frequently mull over what I should add or drop. My list helps me figure out what I want my wardrobe to look like in the long-run, and whether I have too many navy sweaters and not enough grays, or too many fall jackets and not enough for spring. Once something has been on my list for a while, I try keep the item in mind while shopping. And by sticking to my list, I’m able to avoid compulsive purchases. This is especially useful during sale seasons, when one might think that a padded tweed jacket with a faint windowpane check is more worth purchasing than it is. If it hasn’t been on my list for a while, it’s probably not something I’ve thought about long enough. 

Don’t Shop Aimlessly; Have a Plan

If I could only give three pieces of advice to a budding clothing enthusiast, they would be: find a good alterations tailor; learn how clothes should fit; and set a plan for your purchases.

I can’t stress the last point enough. Having a plan means that you’ll be more likely to build a wardrobe of versatile clothes that easily combine into outfits, rather than just a collection of various things that happen to have caught your eye. To set a plan, begin by determining your annual clothing budget. Once you’ve figured out what you can afford, allocate between half and to three-quarters of your budget to shoes, suits, sport coats, and outerwear. These tend to have the biggest ticket prices, but also the highest pay offs. You can easily look great with an excellent sport coat or jacket, even if you’re just wearing it with a mediocre button-up shirt and cheap pair of chinos.

The rest of your budget should be spread between trousers and shirts, and maybe a small amount allocated to sweaters and accessories.

Now go through your wardrobe and figure out what holes need to be filled and what basics need to be replaced. As much as you can, try to cut your wish list in half and double the budget allocated for each item. You’ll always be happier with a small wardrobe filled with higher quality pieces than you will with a large one filled with half-neglected cheap items.

It’s too much to expect that each person out there has the same clothing needs as I do, but if I had to make a recommendation, I would say you should try to acquire two or three pairs of shoes a year, maybe the same in outerwear, and perhaps one or two sport coats or suits per season, depending on your lifestyle. This, in addition to what you’ll purchase in shirts and trousers, should put you on track to building a respectable wardrobe in about three to five years’ time.

I update my list constantly, and frequently mull over what I should add or drop. My list helps me figure out what I want my wardrobe to look like in the long-run, and whether I have too many navy sweaters and not enough grays, or too many fall jackets and not enough for spring. Once something has been on my list for a while, I try keep the item in mind while shopping. And by sticking to my list, I’m able to avoid compulsive purchases. This is especially useful during sale seasons, when one might think that a padded tweed jacket with a faint windowpane check is more worth purchasing than it is. If it hasn’t been on my list for a while, it’s probably not something I’ve thought about long enough. 

Q and Answer: What Should I Get for My Second Pair of Dress Trousers?
Chris writes: I mostly wear jeans and chinos, but I’m slowly working my way towards a more work-appropriate wardrobe. As such, I want to pick up another pair of wool trousers, but I already have grey flannels (though they don’t fit very well). Would you recommend I buy another pair of flannels, a tropical wool, or a four-season wool? Due to a limited budget, I probably will be only getting one pair for the foreseeable future.
If this is your second pair of dress trousers, and you don’t see yourself buying another pair any time soon, then you probably want something that will work year round. This will partly be determined by their weave, material, and weight. Fabrics with very open and porous weaves, such as tropical wool for example, will leave you freezing for half the year, and materials such as cashmere will be too warm during the summer. Choose something that’s neither too densely or openly woven, and made from pure wool. 
There’s also the weight to consider, though this is less important than the weave or material. A standard medium-weight cloth is between ten to eleven ounces. Those above are considered heavy; those below light. Depending on the weave and material, most people consider mid-weight wools to be year-round fabrics, and generally wearable in all but the most sweltering of environments. 
As soon as you can, however, I encourage you to switch to seasonal fabrics. You’ll get a more varied and stylish wardrobe, as nothing is better than when your clothes reflect the season’s mood. Tweed for the fall, linen for the summer. You’ll also find that once you can play around with the weave and material, you can wear slightly heavier fabrics. Heavier cloths feel better, drape more beautifully, and lay smoother. They’re much more elegant and should be favored any time they can be worn.
Plus, since few places in the world have true temperate climates all year, “year round” wool fabrics are often just too hot in the summer and too cool in the winter. For now, you can throw wool long johns underneath to get by in the winter, but get some seasonal trousers when you can. 
In addition to their weight and warmth, you’ll also want to consider durability. Since you’re not planning to buy another pair of dress trousers soon, you’ll need these to last as long as possible. As lovely as woolen flannels are, they’re not very durable, so they shouldn’t be worn every day. If you really want flannel, get worsted flannel instead woolens. These will have a visible diagonal weave at their base and wear a bit harder. There are other worsteds to consider as well — gabardine, nailhead, sharkskin, etc. Which you choose is a stylistic choice. Whatever you choose, however, avoid wools with a “Supers” number above 120, as these will wear out a bit too quickly for you.
Finally, there’s color. For your second pair, there’s really only one choice: a solid mid-grey wool. These will go with almost anything. 
If I were choosing for myself, I would go with these Tasmanian wool or pick-and-pick trousers from Howard Yount. For something a bit more silky and lightweight, he also sells these 9 oz four-season wools. 

Q and Answer: What Should I Get for My Second Pair of Dress Trousers?

Chris writes: mostly wear jeans and chinos, but I’m slowly working my way towards a more work-appropriate wardrobe. As such, I want to pick up another pair of wool trousers, but I already have grey flannels (though they don’t fit very well). Would you recommend I buy another pair of flannels, a tropical wool, or a four-season wool? Due to a limited budget, I probably will be only getting one pair for the foreseeable future.

If this is your second pair of dress trousers, and you don’t see yourself buying another pair any time soon, then you probably want something that will work year round. This will partly be determined by their weave, material, and weight. Fabrics with very open and porous weaves, such as tropical wool for example, will leave you freezing for half the year, and materials such as cashmere will be too warm during the summer. Choose something that’s neither too densely or openly woven, and made from pure wool. 

There’s also the weight to consider, though this is less important than the weave or material. A standard medium-weight cloth is between ten to eleven ounces. Those above are considered heavy; those below light. Depending on the weave and material, most people consider mid-weight wools to be year-round fabrics, and generally wearable in all but the most sweltering of environments. 

As soon as you can, however, I encourage you to switch to seasonal fabrics. You’ll get a more varied and stylish wardrobe, as nothing is better than when your clothes reflect the season’s mood. Tweed for the fall, linen for the summer. You’ll also find that once you can play around with the weave and material, you can wear slightly heavier fabrics. Heavier cloths feel better, drape more beautifully, and lay smoother. They’re much more elegant and should be favored any time they can be worn.

Plus, since few places in the world have true temperate climates all year, “year round” wool fabrics are often just too hot in the summer and too cool in the winter. For now, you can throw wool long johns underneath to get by in the winter, but get some seasonal trousers when you can. 

In addition to their weight and warmth, you’ll also want to consider durability. Since you’re not planning to buy another pair of dress trousers soon, you’ll need these to last as long as possible. As lovely as woolen flannels are, they’re not very durable, so they shouldn’t be worn every day. If you really want flannel, get worsted flannel instead woolens. These will have a visible diagonal weave at their base and wear a bit harder. There are other worsteds to consider as well — gabardine, nailhead, sharkskin, etc. Which you choose is a stylistic choice. Whatever you choose, however, avoid wools with a “Supers” number above 120, as these will wear out a bit too quickly for you.

Finally, there’s color. For your second pair, there’s really only one choice: a solid mid-grey wool. These will go with almost anything. 

If I were choosing for myself, I would go with these Tasmanian wool or pick-and-pick trousers from Howard Yount. For something a bit more silky and lightweight, he also sells these 9 oz four-season wools