Here are my top nine picks for this month.

Economy

Target Mossimo Henley: One of the best-kept secrets of cheap but well-fitting mens clothing is Target. It’s where I go for my V-necks and my socks because it doesn’t cost an arm and a leg, the fit is surprisingly good, and there are a ton of color options. A few years ago the Mossimo line at Target offered an awesome henley. It went away after only one season but it looks like it’s back. $13

Forever 21 Marled Striped Socks: The upcoming cooler weather is going to demand warmer socks. Something thick with some pattern will do great under a pair of dark jeans and your work boots. $3

Topman Chambray Tie: While chambray may be associated with spring and summer, it’s a great transitional material for the first few weeks of fall. It comes in the traditional blue or a more attention-seeking red. $20

Coach

1901 Canyon Chukka: Nothing says fall quite like desert boots. They’re not as heavy or large as your winter boots but are better suited for the changing climate than the espadrilles you’ve been wearing all summer. $100

Cheap Monday Slim Fit Chinos: There’s nothing memorable about these – which is exactly what you want sometimes. Pair them with a plain T-shirt or a polo when you want to fly under the radar without looking like a man child. Ideal for attending all of fall’s many sporting events. $75

J Crew Wallace & Barnes Bedford Cord Jacket: Between the corduroy and the cut of the jack, this is definitely a work jacket – something you’ll want with you for trips to the cabin or just cooler nights in the backyard. $140

First Class

Brooks Brothers Football Leather Penny Loafers: Because football. $350

Barbour Powell Quilted Jacket: The quilted trend that started picking up momentum last year is going to hit its stride this season. If you’re going to get in on it, why not do so with one of the most popular outdoor brands out there? Barbour makes the real deal and this thing should last through plenty of hunting seasons. $250

Natural Selection Denim Raw Narrow Leg Jeans: Slim without looking like you pulled on your girlfriend’s pants, these are a selvedge denim that just gets better with age. The color is perfect and there are no frills, so people pay attention to you and not the weird, bedazzled pattern on your back pocket. $255