I guess you could best describe my style is having its roots in American prep or the Ivy League. Sure, the fabrics, cuts, quality and fits have changed, but today I more-or-less dress like I did in high school and college. Back then, the labels in my wardrobe read Brooks Brothers, Woolrich, Eddie Bauer, Lacoste, and Polo Ralph Lauren. My shoes of choice were Bass Weejun penny loafers, camp mocs from L.L. Bean, Sebago dockside boat shoes and Adidas Stan Smith sneakers. Socks were worn only in the sub-zero months and I still follow this practice today. As a twenty-something, I was a fully paid up member of the ‘new preppy’ movement of the ‘80s and the Preppy Handbook edited by Lisa Birnbach was my Bible.

I wasn’t alone with this obsession of preppy style, either. Sure there were goths, jocks and metal-heads, but preppies ruled in my high school and preppy clothes were a uniform that came naturally to the middle class, upstate New York town where I grew up. My peer group obsessed about the details of their clothes – the width and length of your khaki chinos, the pop of a polo collar or even the length of your Brooks Brothers Oxford boxer shorts, which would peek out from underneath your cut-off’s or rugby shorts on occasion. The arrival of the latest catalogue from L.L. Bean had all the excitement of Christmas morning.

Ivy style has carried into my adult life seamlessly. My Winter wardrobe is chock-full of heavy tweeds from Harris and Fox Brothers for cold winter days in New York and most of my outerwear still reads Woolrich on the label. I have a substantial inventory of vintage fisherman knit sweaters from L.L. Bean and Orvis, and I still care very much about the fit of my khakis. In summer I no longer have my underwear sticking out below my shorts but I own lots of Madras sport coats, (patchwork madras being my favourite) seersucker and linen tailoring.

My taste in shirts has been the most consistent in terms of carry-over from my high school days. The button-down Oxford, (my first was from Brooks Brothers, naturally) is still the most prevalent cloth in my shirting arsenal. I stick mostly to white and blue with the occasional pink one thrown in for good measure. Of course, Oxford cloths are a perennial Thomas Mason favourite too (and there are Oxfords dating back to the 1860s in their fabric archive), which makes them a great port of call for a fabric that makes up beautifully into a proper button-down. That said, alongside my button-downs, I also keep a few spread collar Royal Oxford cloth shirts in my closet too. They’re just that little bit finer – perfect with a tie or open-necked in the summer beneath some of the aforementioned seersucker or bleeding madras.

I’ve taken to wearing overshirts and safari jackets lately as well. I like how well they travel. They’re practical with many pockets and can be dressed up or down with ease. My travel shirt of choice is a lightweight jersey or a well-washed Oxford (check out Thomas Mason’s Journey collection if you haven’t yet), which are always part of the packing routine when I travel. In fact, I usually pack pretty much the same thing depending on the climate, and as a notorious over-packer it seems I have the same amount of clothes for a 10-day trip as a two day trip. I always bring along white denim (yes, all year round), plus heavy twill overshirts in cool months and linen in warm ones.

When it comes to dressing up, if I’m travelling I’ll often layer an overshirt over a ‘smart-ish’ shirt and knit tie in the evenings. Broadcloth is another preppy favourite, of course, which I often use for dress shirts – or else a mid-weight poplin with a fine stripe to it. My other dress shirt go-tos are chambray in fall and lightweight seersucker in summer – and I rely on Thomas Mason for both.

As for other elements in my travel wardrobe; I’ll wear a Barbour if rain is expected (I own piles of them) and they make for nice overcoats as well. Shoes are mostly suede loafers these days, and my L.L. Bean mocs have been upgraded to Quoddy (still proudly made in Maine). A cashmere roll or V-neck is a year-round item I pack or wear on the plane and it seems that more than ever I try to keep to a very specific uniform in terms of colour. I go for neutrals with lots of khaki, grey, navy and white. I think these days it pays to respect the classics – and of course, to heed the teachings of Birnbach’s Preppy Handbook above all else.