Several years ago, I lost 75 pounds and had to rebuild my wardrobe from scratch. I live in Washington, DC and am happy to have a “white collar,” non-profit job that requires a suit four days a week (no need for one on “Casual Friday”). I do a fair amount of business travel and since I may get called-on to do a TV appearance with only a few hours notice, I need to dress accordingly. Hence, I’ve had a chance to do in real life what so many of you fantasize about on this board; build a serious, tailored, multi-season wardrobe from scratch. Learn from me. Your first four suits will be versatile mid-weight essentials that can be worn year-round (9 ½ - 11 oz). Purchase #1 will be a single-breasted darkish grey or darkish blue suit with notched lapels. Doesn’t really matter which; go with whatever color you like best. Purchase #2 will be whichever of those two suits you passed on for purchase #1. If possible, both should be purchased with a vest to make it more comfortable to wear in the winter. Purchase #3 will be a double-breasted darkish grey or darkish blue suit (again, your call). Purchase #4 will be whichever of those two suits you passed on for purchase #3. With these four suits, you can go through life appropriately dressed for any occasion calling for tailored clothes. These are workhorse suits that you’ll be wearing a lot (at least for a while), so you want only subtle texture so as to be appropriate in the most environs possible and so as not to call attention to the fact that you only have a few suits (for now). Choose between pick & pick (sharkskin), a subtle herringbone, nailhead, and tic-weave. Your single-breasteds are your default suits for typical business wear. Your double-breasted suits are when you want to be a bit dressier; grey DB for daytime, blue DB for nighttime. Re color, if you are a high contrast type (light skin and dark hair), you will likely look best in navy blue and charcoal grey. If you are anything else, you’ll likely look best in marine blue (a shade a bit lighter than navy with a green tone) and Oxford grey (a slightly lighter grey than charcoal). To minimize sartorial boredom, consider a marine blue and Oxford grey SB and a navy blue and charcoal grey DB (the darker colors are incrementally dressier, which comports well with the DBs). If you’re on a relatively tight budget, your two SBs can be RTW because if there’s one thing the merchandisers can provide, it’s dark, mid-weight SBs in subtle texture. But if you can manage it, save up for bespoke DBs. It’s awful hard to find a well cut, well fitted DB off the rack. Somewhere in here (probably after you’ve got the SBs) you should get a lined tan trench coat so that you can handle cold weather and warm, wet and dry. If funds allow, supplement the trench with a navy blue, charcoal grey, or tan knee-length overcoat for colder weather (make the tan a polo coat if you’re going in that direction). Your shoulder season suit rotation is now adequate. If you have one or more black-tie functions a year, you will now buy a complete soup-to-nuts rig. If not – or once you have – you now purchase two odd jackets; a navy blue blazer (or a textured blue odd jacket if you can’t stand metal buttons) and a patterned, earth-toned, mid-weight tweed. The blazer should be a serge; a blue odd jacket could be in a small herringbone, Donegal, or something of that nature. The latter should feature a tasteful pattern (large herringbone, gun club check, windowpane, etc.). You will wear these odd coats on Casual Friday, on weekends, and for all of those ridiculous “business casual” events. The blue coat will be for “city” occasions and the tweed for “country.” You will pair them both with (tailored!) mid-grey flannel trousers. While you don’t need to see a tailor to get the business shirts you’ll need (and hence, it’s off-topic) you will want to see a tailor to get at least one – and preferably several – custom white shirts. These will be for your dressier occasions but can also be worn whenever you want to look sharp. Medium point collars are the most versatile and best for four-in-hand knots (which you should be tying). Spread collars are more stylish but may not look good on the round-faced and are less useful away from the suit. If you live in a locale with major seasonal temperature changes (like I do), you will next want to either concentrate on summer or winter suits depending on whether the most extreme temperatures you’re going to face come in the warmer or colder months. DC is far more hellish in the summer than winter, so I turned next to warm weather suits. Warmer weather calls for lighter shades, so pick either marine or airforce blue for your single-breasted and a single-breasted Oxford or Cambridge grey to go along with it. Again, these are workhorse suits, so go with subtle texture. DBs are hard to wear comfortably in the summertime, so forgo those and opt instead for your first run at patterns. This trades off the DB’s “dressiness” for a different kind of style. Choose two; a mid-to-light grey with cream pinstripe, a navy blue with cream pinstripe, a black & cream glen plaid, or a black & cream mini-houndstooth. If you’re buying RTW, you’re pretty much forced into buying tropical wool. Linens are available, but they’re too casual for suit & tie business wear. If you’re going bespoke, however, you have more choices. Choose between fresco, mohair-wool blends, and the better tropical wools. If you have a really dressy, summer nighttime occasion, suck it up and break out your mid-weight, dark blue DB. That’s because pinstripes are associated with business and you don’t want to suggest business after hours. If you have the funds and you like to dress up in the heat of the night, however, you would be well-advised to pick-up a black mohair suit for exactly this purpose. One can easily rationalize skipping the winter suits given the warmth of modern offices and the ease in which an overcoat can keep us warm outdoors. But … skipping the winter rotation deprives you of heavy cloth (which drapes like a dream) and the killer look of flannel which is too warm wearing during any other season. A mid-to-dark grey flannel suit is perhaps the most handsome suit one can wear, so this is your first priority. A dark blue suit makes sense for all of the reasons it made sense in our mid-weight wardrobe, and since flannel looks better in grey than blue (the mottled texture is easier to see and the grey is flecked with black and white giving it more interest), this is a good place for the heavy worsted in pick & pick (if you want a little texture) or birdseye (if you want a little more). If you like or need to be dressy more often than not, go with DBs. If not, go with SBs and a vest for each. Stripes look best on flannel suits, so it would be a shame to not capitalize on this for our winter rotation. Pick two; cream chalk stripe, cream pinstripe, cream windowpane, or black & cream glen plaid, all but the last in either dark blue or dark grey flannel. All but the glen plaid work best as DBs (the glen plaid has its origins as a “country suit” which puts it at a bit of tension with the dressier nature of a DB). These are your essentials. From here, indulge. Like brown suits, tweed, linen, unusual fabrics like dupioni silk, unusual suit patterns like shepherd check, or blazers for all seasons? Need to work on your “in-between” wardrobe (when neither suits nor jeans/chinos will suffice)? Go nuts. Your bases – thanks to my taste and your money – are covered.