Starting Over Part III
A Suit
Welcome back and thank you all for subscribing to my Substack. This next set of items will be more specialized, but are still what I would purchase next if I were starting a new wardrobe. Here is a link back to the first and second article for your reference. Starting Over, Starting Over Part II. For part III, I would focus on getting a suit and the appropriate accoutrements.
A Suit. I am starting here because I know I will get some pushback, but if you have ever needed a suit for a wedding, job interview or parole hearing, then this is for you. A basic, single breasted, notch lapel, navy or dark gray suit will get you through nearly every formal situation that could possibly come up in your lifetime. You will end up getting one and some point so you might as well make it an informed decision. Suits are fitted by chest size, so a 44R means the suit is cut for a 44 inch chest and will have corresponding pants, often a 36 waist. Lucky for you, there are lots of options out there, but the real key here is fit. I like a high rise pant with pleats and room in the jacket to allow for a sweater. If you visit a shop that specializes in tailored clothing, you will likely get a better fit in the end. And keep in mind, almost every suit will need to be tailored once you purchase it, sleeves shortened or lengthened, trousers hemmed. Suit Supply has been making great stuff for years and has an in-house tailor if you visit one of their flagship stores. I like their Havana and Milano cuts. Spier & Mackay makes nice suits as well. Go for their Ellis for something traditional or Neo for something a bit more casual. Trad shops like O’Connell’s and J.Press will carry sack suits which can have a bit less shaping to them, due to the lack of a front dart, but still look great. Ralph Lauren makes some nice suits, but may fit a bit slim and come with flat front pants. Proper Cloth has moved into MTM suiting as well, which I have yet to try personally. I do like how they look however, the VBC Allen suit is a stand out in Charcoal and Navy. I did officially order their Fresco Downing suit as well which I will report back on once it arrives. If you want to go for something truly custom you can have bespoke suit made, but be warned now, there is a lengthy process involved and the prices can be very expensive. The two I have used the most are Sartoria Pastena Elegance and Ercole’s.
A white dress shirt. Yes, this is different from the white oxford cloth shirt mentioned in Part II. This item, like the suit is a commodity you should not overlook. It should have a point collar, no pockets and long enough to tuck into your pants. The cloth can be any number of weaves, but a basic twill or pinpoint works great. Proper dress shirts are sized by the collar and sleeve length, so a 17.5/34 means the neck is a circumference of 17.5 inches and a sleeve length of 34 inches measured from the center of the shirt back where the yoke meets the collar. Because this is a fitted garment like the suit, it would be best to get measurements taken by a tailor so you know what size shirt to get, or try them on in person. The collar should be snug but not tight. Proper Cloth provides this service remotely and I have had a lot of success with them over the years, I like this one. There are options in every price point here, I like these from Todd Snyder, Sid Mashburn, and Gitman Brothers. For less expensive options, I like these from The Tie Bar, Charles Tyrwhitt and Spier & MacKay
A pair of black oxford cap toe shoes. Oxfords are recognizable by their curved throat and closed laces that make a subtle V-shape from the vamp to the top. These, admittedly are my least worn shoes. They really only make sense when worn with a suit and thus not very useful throughout your wardrobe, however, they complete the proper look when wearing a suit. I didn’t make the rules and I wouldn’t stray from them here. Just be sure to give them a good brushing before you wear them and when you take them off. I tend to like traditional British brands like Crockett & Jones and Edward Green but they are pricey. Check out Meermin, for a more budget friendly option that are still really well made. A few more options from Carmina, Alden, Allen Edmonds, Myrqvist and Morjas.
A black tie. Specifically a textured black tie. More specifically a 100% silk, black, textured tie. If you are still with me here, I promise you, this can be the only tie you ever purchase, so get the right one. There are definitely more interesting options, colors, types, but a dark solid grenadine is my favorite. Grenadines come in fina and grossa, fine and chunkier weaves. I like these options from Buck Mason, Drakes, The Tie Bar, Charles Tyrwhitt Todd Snyder, Sid Mashburn and Proper Cloth.
A white linen pocket square. I love a good printed pocket square, but a simple white linen with a TV fold will always look clean and polished. They can also be used to wipe a tear or dab up a spill in a pinch, just don’t blow your nose in them, that still baffles me. I like the ones that have a hand rolled edges, but certainly not a necessity. I am sure there are plenty of options out there, but I like these: Todd Snyder, Turnbull & Asser, Proper Cloth and The Tie Bar. I would also keep an eye out when in thrift shops, they typically have some in with the cloth napkins, just look for the hand rolled edges.
Over the calf socks. Specifically ones that match the color of your suit, so navy or gray. If you cannot find a match, opt for a shade that is darker than the suit cloth. Over the calf is fairly self explanatory and I like merino wool personally, just be sure they are a fine gauge, light weight and no patterns. Bresciani make my favorite but there are some other brands that are excellent as well. Macrolani, Mes Chaussettes Rouges, Pantherella, and Drake’s.
A local seamstress or tailor. Obviously this is not an item you can purchase, however if you ever need something altered or hemmed, taken in or out, a seamstress or tailor will be your best asset. Most suits will have additional cloth built into them to allow for changes if you gain or lose weight. Up or down one whole size for most and a possibly a bit more. I also love knowing my tailor can check the fit of a suit before I decide to keep it or not. I wouldn’t make a habit of it, but my tailor Simon will let me know, often without remorse, whether something fits me or not. This is invaluable information because it can save you a ton of money in purchasing garments that don’t fit, or cannot be altered to fit. Just remember to plan these visits, don’t show up 2 days before the wedding needing a suit altered. Also, don’t go when you’re in a hurry, smile say thank you, leave them a tip or bring a small gift or token of appreciation. I try and introduce my friends to my tailor, who appreciates the potential business. My friends are always shocked to learn that their favorite shirt, the one with the sleeves that are too long, can be shortened. To find one you can check Reddit or ask where you bought your suit. If you are unsure as to the quality of their work, you can ask to see something they altered or bring them something thrifted first and see how it turns out, this way the financial risk is a bit lower.
That is it for Part III. Unlike the previous two articles, these items really do need to be worn together. However, when combined, these 6 items and the work of a good tailor, will make you look as good as you possibly can in an article of clothing. Fit, fit and fit should be your focus and a good tailor can help a ton.
-DL-








What has your experience been like with Sartoria Pastena? Is it truly bespoke? Trousers with significant handwork? Approx cost?
Local tailor is 100% the way to go. Search yelp for recommendations, hunt around, and you’ll be surprised what’s around. A good tailor is worth their weight in gold and worth spending the time to find.
About a decade ago I found a small local tailor in a major west coast city that did me a bespoke three piece for less than $1000. One of the best suits I own, still going strong after 13 years, and much better value than the made to measure Saville Row suit I had done a few years prior to that.