What to Pack on a 3-Week Trip to Scotland and England in Early Autumn

[In anticipation of a similar trip we’re taking in 2026, I updated the links below to products available in 2026. All dead links should be fixed. This post was originally published in 2017. Links below are affiliate links that earn me commission when you make a purchase.]

My wife and I are excited to soon be embarking on a three-week trip to Britain. We’ll be spending just over a week in Scotland, just over a week on the coast in southwest England, and a couple days in London on the tail end.

I looked at historical weather data for the past 6 years for the autumn months to get a feel for the highs, lows and averages we should expect. Basically, it’ll be weather like I’d expect in northern Indiana where I grew up at this time of year—with perhaps a bit more rain. For the part of our trip in Scotland, we are going to road trip through the Highlands, making it all the way to Skye (stopping in Glencoe along the way, with lots of other vistas planned), plus a day trip to Islay as well as sightseeing Edinburgh and Stirling. In England, I’ll be dressing in coat and tie for at least part of every day. And in London, we’ll be primarily sightseeing the main attractions.

We like to travel carry-on only when possible. That means I have to pack versatilely, expecting to get multiple wears out of what I bring, and being able to mix and match so I don’t repeat outfits much if at all. I’m checking a bag on this particular trip, since we have a direct flight (meaning lost luggage is much less likely), since we’ll have a car for much of our time there (meaning we won’t have to lug massive bags all over public transit between cities), and since our airline includes it for free in our ticket price. That said, I’m saving room to bring home some Scotch and still trying to maximize my available luggage space. And I’m sure my wife will ask to use some of my checked bag’s space, too.

So, all those things considered, here is my packing list. I’ll write a post after I return to let you know how well it went. Not pictured is one crewneck cotton sweater (arrrgh forgot to lay it out in this flat lay), and of course socks, undergarments and sleeping attire.

2 sportcoats

• 1 Navy Fall-Winter weight sportcoat (similar from SuitSupply [new 2026], or from Cavour [also new in 2026], or from Besnard [new in 2026] or from Natalino)
• 1 Brown F/W weight Donegal sportcoat (somewhat similar from from Cavour [new 2026] or from Besnard [this is the best-matching to the silhouette of mine tbh]

5 button-up shirts

• University stripe OCBD (make one with the Soft Ivy Button-Down from ProperCloth with code MUSINGS10 for 10% off)
• White spread-collar dress shirt (the ultimate may be from Cordon 1956)
• Light blue cutaway collar chambray popover (in 2026 this Drake’s looks fabulous)
• Light blue-stripe linen-cotton cutaway collar shirt (similar pattern in all-cotton from Thomas Mason at ProperCloth where MUSINGS10 gets 10% off)
• Blue OCBD popover (make one with the Soft Ivy Button-Down from ProperCloth with code MUSINGS10 for 10% off)

4 pairs of trousers

• 2 pairs denim (one medium fade [similar from Todd Snyder 2026], one light fade [similar from Todd Snyder 2026])
• 2 pairs chinos (one khaki, one British khaki, in 2026 I’d get them from Bill’s Khakis)
• 1 pair light grey flannel trousers (ProperCloth is my trouser go-to now because I dial in my fit perfectly, MUSINGS10 gets you 10% off)
• 1 light grey cotton pullover sweater (not pictured, in 2026 I’d get this cashmere one from Sid Mashburn

3 ties

• Grey cotton POW tie (similar in 2026 from ProperCloth, use code MUSINGS10 for 10% off)
• Navy cashmere knit (similar in 2026 from N.Peal or one from Besnard)
• Navy medallion ancient madder [in 2026 I’d buy one from Shibumi Firenze]

2 pairs shoes

• Scotch-grain Peal & Co. brogues w/ Dainite sole (similar from Myrqvist in 2026; in 2026, Allen Edmonds has these longwings; but in 2026 I’ve switched from wingtips to split toes like these beautiful TLB Mallorca’s, my favorite shoe brand)
• Snuff suede Meermin chukkas w/ Dainite sole [in 2026 my preferred chukkas are from Myrqvist]

• 1 Barbour Ashby 
• 1 Navy cashmere scarf (similar; use code MUSINGS10)
• 1 Travel Umbrella