Closet Makeover: 15 Must-Haves to Have You Dressed in No Time

Keep: Once you’ve found a timeless navy suit that has been tailored to perfection, absolutely hold on to it. A sophisticated stripe, like this one from Hugo Boss will always be appropriate – for an important business meeting or a more formal event. Like our Find here, you want to ensure the fit is close to the body, with narrower lapels, to look appropriately updated. This suit is worth the investment, looking elegant with a white spread collar shirt, as well as a solid blue or pattern shirt. Black or brown shoes finish the outfit. Hugo Boss even offers many free alterations, so if you have a store near you just bring it in when you have time, along with the included invoice, and they’ll do the rest.

Add: A plaid dress shirt will freshen up your “keeper” suits and sport coats. This blue windowpane check pattern from Eton updates any navy or grey, and is subtle enough to be worn with stripes, too. The contemporary fit is trim to lay smoothly under your jacket. With a spread collar and mitered barrel cuffs (meaning, it’s a buttoned cuff with the corner cut at an angle), it is very professional and upscale-looking. For almost 90 years, Eton has been using luxurious fabrics to make exquisite shirts, so this is an addition worth making – it will be a “keep “ for years.

Keep: While you don’t need much advice from us on the merits of your favorite hoodie, we can confirm that it’s perfectly acceptable to keep it hanging around. Comfort is always in style, as long as it still looks good and fits well. Obey’s version is made of a super comfy cotton that is a nice quality, so it washes well, too. It comes in a few colors, and this navy is our top pick for jeans, khaki’s, and sweats. It’s the ideal weekend go-to for lounging on the couch or making a coffee run.

Add: Beefy shawl collar cardigan sweaters are a fresh update to replace a sport coat or add a little casual style to your button up shirts and t-shirts. With ‘70’s inspirations in full swing, this is a great way to get in on the trend in a very wearable way that won’t look like you’re playing into any style fads. This Bonobos’ cotton 5 button cardigan in navy works great with dark wash jean, khakis or dress wool pants. The modern fit isn’t too oversized, and tailored just enough so the heavy cotton won’t overwhelm you. It also comes in a charcoal grey (through the 'shop it' button) that dresses up with ease.

Keep: Check shirts in neutral colors never go out of style, so hang on to yours – especially this season, when prints and patterns are so important. This grey check from Bugatchi is always in style, under a navy blazer at the office or with dark wash jeans on the weekends or for an evening out. The modern fit is easy, but updated so it’s not too oversized, with all the finishing details that make this shirt one for the ages - a shorter spread collar, sleek taping on the placket, and a stylish contrast trim on the cuffs. We are sending you to Patrick James’ website, where they will provide a pre-paid return label if it doesn’t work out, so you can buy with confidence. If you’re not familiar with this store, we think of it as the West Coast version of what Mark Shale’s retail stores were like – filled with an edited assortment of timeless high-quality pieces from many of the same brands we used to carry and still recommend.

Add: While plaids and checks never go out of style, prints of all types look very current this season. The space print of this Vince shirt is just awesome – very modern, but not trendy – in an abstract geometric indigo blue and white pattern that looks great with jeans and any color twill pants. It looks great on its own or under a blazer or fashionable shawl collar cardigan. The contemporary fit is trim, ensuring an updated look that is perfect with this print.

Keep: Flat front chinos are another wardrobe staple, especially in soft washed cotton that’s cut with a straighter leg. It’s a style that is perfect for the office, the weekend or an evening out. Bonobos, a line that started out with a focus on pants, really nails this style. The “chestnuts” color we’re featuring is perfect for Fall/Winter, in its darker neutral shade that will work with all your button up shirts and sweaters. They really nail the fit - and not just one. These great basic chinos come in 3 different fits: Tailored (the trimmest, contemporary fit), Straight (a modern “everyman” fit that is still updated and current), and Slim (which is in between the two). Besides choosing your waist size, you can also choose an inseam length that is right for you.

Add: We’ve talked about the “athleisure” trend in the past, and it’s still going strong for the season to come. Take advantage of it and add these utility joggers to your pants collection. They take the perks of a pair of sweats – like elasticized cuffs and a half-elasticized waistband – and combine them with a style that also reflects the ever popular military inspirations we gents love in our casual pants (that is luckily, quite stylish this season). Gap does some things really well and casual pants like these are certainly one of them. They are well-styled with seamed details at the knees and back button flap pockets. The black moss is a versatile shade of green that will work with everything in your closet, from t-shirts and thermals to button up shirts and casual sweaters. And the garment dyed cotton canvas is soft and durable. Consider them a modern replacement for your casual khaki pants and sweats. And a great way to add some fashion at a really good price.

Keep: Really, what’s to say here? A long sleeve grey t-shirt is a key layer for any gent. As long as you’ve got one that still looks good, it’ll surely be put to good use this season – and in those to come. The Tommy Bahama one we’re featuring has a higher v-neck, which looks great under sweaters or sport shirts. And the cotton/Tencel blend is not only super soft, but it holds up wash after wash, so it will be a “keep” for a long time.

Add: Once you’ve got the basics down, a sweater with some pattern is a great addition to your closet. J.Crew’s striped sweater is made of slub cotton, so it has great texture that gives this dark navy and red stripe a perfect cold weather feel, without being too heavy. The whole look takes on an updated athletic look that is so current – and easy with jeans or your nicer navy sweatpants. The fit is typical J.Crew, modern and easy without an oversized, sloppy look.

Keep: Finding a great pair of jeans and breaking them in to perfection is nothing to dismiss lightly. So we know you’re going to want to hold on those, and that’s great. Jeans that fit well, make you feel good, and most importantly, are comfortable are any gent’s best friend for every non-dressy occasion. Let’s clarify “fits well”…yes, they should be comfortable, but they should also have a modern silhouette, like these AG Jeans in their Hero model. They sit a little lower on the waist than jeans from a few years ago, with a straighter leg that has a slight taper to work with all the current sneakers, oxfords, and chukka boots. Washes range from dark to broken-in, so this featured pair’s dark wash with subtle natural fade is just right.

Add: Shoes make the man (or something like that), and they can ruin an outfit so make sure yours are updated and looking smart. Chukka boots (ankle length boots that usually have 2-3 pairs of eyelets) will give your jeans and twill pants an instant update. OluKai uses a black nubuck leather to give the black color a broken-in feel for just the untailored look you’ll want. The design is a cross between and sneakers and leather boots, so it works with all of your casual pants.

Keep: If you’ve already invested in a great down puffer to get you through those cold days, hold on to it. They remain a practical, and still fashionable, way to keep warm during the Winter months. And as Chicago veterans, we know just how rough those snow days can really be. This jacket from The North Face is one of our top picks for its breathable, water resistant shell, insulated hood, and a 550 down fill (which will usually keep you warm down to about 20 degrees). On cold days, you’ll be glad you have it, whether you’re heading to the office or just running around town.

Add: Gents often focus on ensuring they have the right hardcore cold weather coats, but a lightweight rain shell is equally important. Often worn by bike riders, it has become part of the athletic look that is so relevant in men’s fashion today. K-Way has been making great-looking, functional raingear since 1965. And this lightweight, packable rain jacket is one of their best. Besides having the functional necessities, like a drawstring hood and back storm flap, it doesn’t miss out on style with K-Way’s signature stripe around the zipper. It looks great with jeans, khakis, shorts, and sweats. It even comes with a waist bag that has an elastic belt so you can easily bring it with you on an overcast day.