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Making good choices when you first start wearing tailoring is difficult, I know I didn't.
The temptation is to buy bold suits. They're exciting and you want to stand out, but I promise you'll come to regret those flashy early purchases. It's far better to buy classic, and yes, conservative suits at first.
You should do this is for two reasons. One, your tastes will change rapidly and that pattern you love today will likely revolt you in six months to a year. And two, when you have fewer suits, the more distinctive they are the more apparent it is when you wear them more than once a week, as you will have to do.
If you're wearing a suit to the office four or five days a week, you need a minimum of three suits, but as they need rest between wears, five suits is a goal you should work towards over time.
Your first suits should be four-season worsted wool, you want to be able to wear them year-round and worsted wool is the most formal fabric. For style, they should be single-breasted, two buttons, have notch lapels of moderate width (3-4 inches), flap pockets, and side vents.
Avoid bright colored linings or colored button holes as these will detract from your formal business look. I also recommend against ticket pockets, you're trying to keep these suits as simple as possible. Lastly, ensure your suits are at least half canvas construction. A fused suit can't breathe, looks bad, and will wear out sooner.
Start with Navy and Charcoal Suits
Your first two suits should be navy and charcoal. They are most business-like and will serve as a base from which you can create interesting, but business-appropriate shirt and tie combinations.
Add a Gray or Blue Suit
The third depends on which color group you prefer more. If grays, add a mid-gray. If blues, add a second suit in a blue a hint brighter than navy. At this point I recommend you pause your purchases and wait a few months.
Cavour Mid-Gray Winter Hightwist Suit
Three suits is enough to get you through the work week without having to wear any of your suits more than twice, which is key to maintaining their longevity. By pausing now, you will have time to reflect on your developing style preferences and inform your next purchases.
Add Another Gray or Blue Suit
After a pause of a few months, your fourth suit should either mid-gray or blue, whichever you didn't select for your third suit.
Don't go any lighter/brighter than this Suitsupply Blue Jort Suit
If you work in an office that has some form of casual Friday or where odd jacket and trouser combinations are an acceptable alternative, you may want to stop at four suits and build out your sport coat collection.
Your Fifth Business Suit: Dark Brown or Add Texture
If however, you need five suits a week or you prefer suits to sport coats, you have more options. I suggest a dark brown which can look quite formal.
A dark brown like this Suitsupply Napoli Suit can work well in the office.
If the idea of a brown suit is unappealing to you, add a suit in your favorite color with a subtle pattern or textural element, such as a faint glen plaid or a herringbone weave.
Five suits is enough for anyone, even those wearing them to the office each day, but if you develop a taste for tailoring and want to acquire more, the options expand exponentially now that you have the basics covered.
A good starting point would suits in the basic colors above, but in seasonal fabrics. Fresco for summer and flannel for winter would be the most business appropriate. You could also add a three-piece or double-breasted suit. Chalk stripes, which are easier to wear them pinstripes, would be another good option.
You could even start adding casual suits in fun fabrics such as corduroy, seersucker, or linen.
Spier MacKay Green Seersucker Suit
Best Places to Buy Business Suits
All this is well and good, but where can you find suits like those described above that won't bankrupt you? I have three suggestions, none of which will be a surprise if you've followed me for any time.
The three brands that you should consider purchasing from at this point are Suitsupply, Spier & MacKay, and Cavour. All offer good quality at affordable prices, which you prefer will depend on you budget, personal style preferences, and build.
The brands differ in several ways, here's a quick breakdown:
Spier & MacKay's suits are the most affordable starting at $328. Some Suitsupply models are as low as $359, but more often $400-$600. Cavour's suits are normally priced between $700-$900, but when they have a sale can drop as low as $350-$400, I recommend you only buy Cavour suits on sale at this point. (They happen to be having a great mid-season sale right now, 30-70% most items.)
Suitsupply offers several models, all which fit slightly differently, but the business basics are most often Napoli or Lazio models. Both are lightly-padded, but the Lazio is a slim fit and the Napoli fuller. Both are shorter than ideal in jacket and sleeve length.
Spier & MacKay has two cuts, normal and neapolitan, and two fits, contemporary and slim. The neapolitan is longer and cut so the quarters and lapels form one continuous crescent shape. The slim is quite slim, I would say comparable or slightly tighter than the Suitsupply Lazio. It also has higher armholes than the contemporary, which is cut with more room in the chest and back.
Cavour has one cut (they'll be introducing a second in F/W 20). It is cut generously in the chest and back with nice drape, comparable to the Spier & MacKay contemporary, but with a higher buttoning point.
Suitsupply and Spier & MacKay's entry lines are half-canvas; they both offer full-canvas options, but they are considerable more expensive. Cavour's suits are fully-canvassed.
Spier & MacKay does most of their business in sport coats, so their fabric selection for suits is a bit limited, but covers the basics. Suitsupply is the biggest company and has a numerous fabrics in each of the basic colors. Cavour has a small collection of suits each season, but will generally have most of the colors we've discussed above in a plain worsted and usually in a subtle pattern or texture too.
Shipping & Returns
Suitsupply and Cavour have free shipping and returns. Spier & MacKay offers a free return on your first jacket or suit purchase, but after that charges about $20 per return.
I hope his guide was helpful to you and you can avoid some of the mistakes I made along the way. As always, I'm available via DM or email if you want help with sizing or deciding between several options.
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