Shop Window: 5 Things to Buy This October

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Dressing in style for October can be tricky: the weather’s all over the place, sometimes raining twice in the same day that started off with blue skies and a temperature edging on summer. The key is mastering the art of layering so you can shed or add clothes depending on the prevalence of a stiff northern breeze. Keeping that in mind, here are five on-trend, easy-to-layer items that you can mix and match for the optimal October look.

 
 

The home run jacket : GAP x GQ Bespoken Suede Baseball Jacket
GQ has an eye for the best new menswear designers in the country, and they chose wisely when they founded these guys to help pull off their latest collab with Gap. Bespoken was tapped for this suede athletic jacket, riding off this fall’s athletic trend we helped clue you in on. Elasticated cuffs at the wrists sport high-contrast white stripes while the rest of the jacket is a neutral grey, making it a perfect matchup with pretty much anything you own. Try wearing it with a skinny black tie and a simple Oxford for a look that can take you from the office to a night out with the guys (Gap, $348).

 
 

Classic boots with sole: Original Chippewa for J. Crew Plain-Toe Service Boots
Killer style for the working man. Whereas summer is all about colour, and winter drags out the neutrals, fall style lets you add pops of colour that turn heads—and these sleek black leather kickers from J. Crew have just the right amount. Based on a 1920s design, these boots can take the colder weather but won’t leave you with swampfoot when the temperature unexpectedly rises. The pop of fall favourite orange, on the other hand, will keep your style game hot regardless. Match these with some slim or straight-leg selvedge denim (by which we mean, throw out your boot cut jeans, please). As for up top, these will help dress up a casual tweed blazer or a leather motorcycle jacket, no problem (J. Crew, $268).

 
 

The heavy denim shirt that works: Timberland Earthkeepers Denim Overshirt
Gone are summer’s breathable chambrays, but if you’d like to hold onto your denim shirt just a bit longer, grab this updated (read: heavier) denim shirt from Timberland Earthkeepers for an outer layer when a sweater or jacket is still too much. This shirt oozes urban cool, even if you’re stuck pulling yard work duty. The best part is the dark denim will break in over time, leaving unique creases and colouring as long as you keep washes limited. Wear it on its own or throw it under a cable-knit sweater in a warm colour, such as burnt orange or rust, to tough out even the coldest days, October and onward (Timberland, $98).

 
 

The essential sweater: Plectrum Engineered Stripe Crew Neck Jumper
The rocker look is coming back with grunge style hitting runways, but enough of the plaid, already. Sporting a similar vibe, Ben Sherman’s crew neck jumper throws off some rocker notes with high-contrast striping and colour-blocked hems in a perfect fall colour combo. To really hit the slouchy rebel look, let it stretch out a little bit by skipping the wash for a few wears (just be prepared to fight your girlfriend for who gets to wear it on cold days around the house). For now, stuff it under your favourite cotton navy blazer so you can get a few more weeks’ wear out of it, and when winter hits, make it your go-to for layering under those boring greys and blacks (Ben Sherman, $175).

 
 

Change your fall colours: Zara Camel Coat With Fur Collar
If you really want to up your style game, let fall’s classic colours hibernate for a bit and go straight for the one that shows you really know what’s up: camel. In the case of this overcoat, the colour dresses up anything from your Raptors hoody (seriously) to neutral shirts that no one would otherwise pay attention to. And, unlike brown, it goes with pretty much everything, even black. Pick one of these up from Zara for the end of the month, and you’ll be happy you have an understated fur collar to pull up when things start getting chilly (Zara, $299).

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