If you're wanting to start dressing up a little and are overwhelmed by all the information out there, I'm here to give you a little help. Here’s a quick guide if you’re looking to buy your first few tailored items. I’ve written about why I favor tailoring in other articles (the intro in this review, for example), so if you’re wondering who in the world is going back to blazers and ties post-pandemic, there’s your answer.
Why this guide versus any other guide?
If you like my style—mixing high and low, blazers with jeans—and feel it would work well in your environment, I've put this together for you. At my workplace, the majority of people dress in basic business casual every day (they all have seen me dressing the way I do for years and don’t mention it anymore). Although I work remotely the majority of the time, I spend a not-insignificant amount of time in the office, too (not during pandemics, anyway). My basic approach to tailored clothing is to buy and wear things that look good in this kind of environment—no gray flannel suits at work for me. And what I wear in my office environment translates really well into the rest of my life, too, so it’s an efficient way to dress.
I link specific products in the photo grids for simplicity, but look underneath each gallery for links to additional items from various makers. I try to cover the gamut of prices in the makers I like best. In fact, most of the brands I link here, I've written about either as reviews, or simply as things I've personally bought, like, recommend and wear. Check out my tailored clothing reviews here, and my overall "recommended products" list here.
(Help support this site! If you buy stuff through my links, your clicks and purchases earn me a commission from many of the retailers I feature, and it helps me sustain this site—as well as my menswear habit ;-) Thanks!)
The Basic Professional Tailored Starter Kit
Single breasted navy blazer in wool hopsack (Spier & Mackay | Natalino | Proper Cloth | SuitSupply | The Armoury Model 3 by Ring Jacket)
Mid-gray wool trousers for the seasons
1 pair in fresco/high-twist for the summer (Spier & Mackay | Rota regular rise | Rota higher rise | Natalino | Besnard)
1 pair in flannel for the winter (Rota | Besnard | Proper Cloth | Natalino | Anglo-Italian)
Dress shirts with medium spread collars in solid light blue and light blue stripes; pinpoint oxford or oxford cloth. Add one white shirt in pinpoint or broadcloth. My favorite makers: (Spier & Mackay Custom Shirts | G. Inglese | Proper Cloth Custom Shirts | Besnard | Anglo-Italian | Finamore | Cavour)
Navy tie in grenadine or rep twill for when you need to dress up to impress somebody. My favorite tie makers: (Kent Wang navy grenadine | Drake's Grenadine | Chipp Neckwear grenadine | Granqvist grenadine | Kamakura twill)
Mid or dark brown suede shoes. My recommendations for shoe models: Split toe Norwegians, cap toes, penny loafers, double monks or tassel loafers would all be fine choices. Or you could do Chelsea boots or chukka boots in a shapely last (i.e. not desert boots). My favorite makers for these types of shoes: (Beckett Simonon cap toes | Carmina | Alden | Meermin | TLB Mallorca)
Notes: This will look pretty dressed up in a casual office environment, and it’s the tailored wool trousers that, in my view, take it over the top in that way. If you work in a slightly dressier office, though, this will look great.
If you find that it’s a little too dressy for your environment, here’s my suggestion for what pants to wear instead:
Chinos. Go for stone, khaki, British khaki and fatigue. My favorite makers: (Spier & Mackay | Jack Donnelly)
Chinos are a classic American pant option that look great with a navy blazer. A contemporary fit, with a mid-rise and tapered leg will keep them from looking too much like the Dockers of my youth. I have a few tips on trouser fit on my post Two Tips for Trouser Fit.
The jacket should fit you in a flattering, contemporary way. Look at my post How to Up Your Style Game Without Looking Like an Old Man for some tips about that.
Where to go from there
Other clothes for…
Fancy casual parties, meals or other gatherings
Long-sleeve navy polo for underneath your blazer (Kent Wang | Spier & Mackay | Natalino | Anglo-Italian | Prologue HK spread collar or button-down collar)
Off white mid-rise denim/five pockets (Sid Mashburn | NN07 slim jean | orSlow 107 Ivy fit white jean | Anglo-Italian | J.Crew)
Desert boots or more shapely chukkas if you went shoes above; or go for one of the pairs of shoes I mentioned if you went for boots above. My favorite desert boots: Astorflex Driftflex or Greenflex. My favorite shapely chukkas: Meermin.
Even more dressed down workplaces
Dark rinse, mid-rise, slim straight denim for a more sleek look (J.Crew resin rinse non-selvedge jeans | orSlow 107 Ivy fit rinse denim | RRL slim denim | Polo Ralph Lauren slim-straight dark denim | Sid Mashburn non-selvedge rinse denim | Anglo-Italian dark wash | Gustin crowd-funded slim jeans)
Mid or light-wash denim for a more casual look (J.Crew non-selvedge three-year-wash | Sid Mashburn | NN07 slim mid-wash| Anglo-Italian light wash or mid-wash | Polo Ralph Lauren light-wash slim jeans)
Alternatively, five-pocket pants in canvas and other fabrics: Spier & Mackay | Sid Mashburn
Notes: Here are the two secrets to making a jeans-with-blazer outfit look great: suede dress shoes, and a tapered jean with a mid-high rise.
Suede shoes are important because their texture complements the denim (shiny leather shoes against denim is tricky to pull off just right, so I don’t usually even try); them being a dressier shoe (like a penny loafer, Norwegian split toe, double monk or even a shapely chukka boot) also helps bring those jeans up in formality a little bit.
The jeans need to be tapered (but not skinny) because a baggy pair of jeans just doesn’t look good with a blazer. But it’s the rise that’s a bigger key—too low and it doesn’t play right with the buttoning point of the blazer. I have more about that point on my post Some Thoughts on Jeans With a Blazer here.
Special occasions
Navy suit in heavy fresco or year-round wool (Spier & Mackay navy Minnis Fresco suit or Full-Canvas navy year round cloth | No Man Walks Alone x Carrara 2-ply Drapers suit, N.M.W.A. x Carrara Minnis Fresco Suit or N.M.W.A. x Carrara navy nailhead suit | Suitsupply navy Lazio suit | Boglioli midnight blue virgin wool suit | The Armoury Model 3A high twist navy suit by Ring Jacket)
White spread collar shirt in pinpoint, royal oxford, or broadcloth (Spier & Mackay Custom Shirts | G. Inglese | Proper Cloth Custom Shirts | Anglo-Italian | Finamore | Vincenzo di Ruggiero)
Dark brown leather or black leather cap toe balmorals (Beckett Simonon Durant Adelaides or Dean cap toe Oxfords | Meermin cap toes or punch caps | Carmina cap toes or punch caps)
Notes: owning one nice suit in a dark color is all most people need. I suggest navy but it could be dark gray, too. Either will look good at suit-type events (formal weddings, funerals, church services, etc.). Leather shoes make a suit complete, and black leather in particular is the best-looking, most traditional choice. However, most events these days are not truly all that formal, and a pair of dark brown leather shoes will be just fine with the suit. Brown leather will also look great and less formal with your mid gray wool trousers, meaning you’ll get more mileage out of them.
For more tips, check out my eBook
This is the very basic checklist to starting a tailored wardrobe. Obviously once you buy a navy blazer and some gray trousers, if you want or need more variety, you’ll want to start looking at other colors and fabrics for jackets and pants. This is where my eBook comes in. In it, I give you a framework for understanding tailored menswear, which empowers you to make these choices for yourself (rather than me just saying “Hey you! Buy a tweed sportcoat!”).
(Help support this site! If you buy stuff through my links, your clicks and purchases earn me a commission from many of the retailers I feature, and it helps me sustain this site—as well as my menswear habit ;-) Thanks!)
Shop my clothing from this post and every other post on the Shop My Closet page. If you’re just getting into tailored menswear and want a single helpful guide to building a trend-proof wardrobe, buy my eBook. It doesn’t cost that much and covers wardrobe essentials for any guy who wants to look cool, feel cool and make a good impression. Formatted for your phone or computer/iPad so it’s not annoying to read, and it’s full of pretty pictures, not just boring prose. Buy it here.
