15 Wear Now AND Later Effortlessly Transitional Finds

2. Why is it a Find? J. Crew’s trench coat is what every gent needs to get through those late Winter and early Spring rainy days. The shorter, modern length covers a suit jacket or sport coat for your work and dressier event needs, and it looks just as good with casual clothes. The bonded cotton coat has four pockets – two for your hands and two for your stuff.
Wear it with: Now: Since this jacket is about repelling the water, you can easily layer your wool blazer or chunky sweater under it, so you can be sure to get plenty of use out of it – work or play.
Later: As the weather warms, it is the perfect late spring raincoat that works with your lightweight suits, or khakis and a button up shirt.
Fit Tip: The fit is modern, ideal for most gents, even when layering over heavier pieces. Size up for a truly, easier fit.
Alternatives: We are showing you the versatile navy, and we seriously love the additional vintage fatigue color you’ll also find through the ‘shop it’ button.

3. Why is it a Find? The year round weight of J. Crew’s wool navy blazer makes it a wonderful “wear now” and “wear later” piece. Truly versatile, it has updated narrower lapels and a slightly shorter length to give it modern attitude without being overly trendy. And the quality is truly fine. Its half Bemberg lining is normally only found in much more expensive garments, and really adds to the comfort. (Click through the ‘shop it’ button to see the interior detail images.) This one’s a real value.
Wear it with: Now: For the cold days still ahead, we like it paired with a sweater or sweater vest for warmth and a good seasonal look. It can be dressed up with wool trousers, and thanks to its own fine wool fabric, adds a dapper finish to dark wash jeans.
Later: When the weather warms up, wear it with a brighter color gingham check or a solid button up shirt. We always believe a tie adds a nice finishing touch for any upscale outing or day at the office.
Fit Tip: J. Crew’s Crosby fit is modern with a little extra room in the shoulders and body.
Alternatives: If you prefer a contemporary fit, this blazer is also available in their trimmer, Ludlow model.

4. Why is it a Find? An easy third piece, David Donahue’s fresh berry colored sweater will brighten up a somber cold day, and remind you that you’ll happily wear it all Spring long. The silk/cotton/cashmere blend is a comfortable weight that’s not too heavy, but not lightweight looking, either.
Wear it with: Now: Wear it now with dark pants or jeans and add a blue pattern button up shirt underneath to ground the pop of color in this sweater.
Later: As the temperatures rise, bust out your tan and light grey khakis, or broken-in jeans, and layer it over a white button up or t-shirt for a more casual look.
Fit Tip: The fit is easy with plenty of room for all gents. Size down for a trimmer fit.
Alternatives: There are three other great color options through the ‘shop it’ button, too.

5. Why is it a Find? One of our favorite new pullover designs of the season ahead, Tommy Bahama’s casual style is just right to start wearing now. And the best part, gents, it’s reversible. Click through the’ shop it button to see this cotton sweatshirt in grey. And even when you wear it that way, you won’t lose this awesome Maui blue color thanks to the contrast stitching. The split neck really steps it up from any sweater or sweatshirt you may already have in your closet. Tommy Bahama is a go-to resource for well-made, good-looking weekend staples, just like this one.
Wear it with: Now: Whether you choose the grey or Maui blue color to show off, this top is easy to layer over a white t-shirt with dark wash jeans, twill pants, or sweat pants for a comfortable weekend outfit.
Later: When the weather gets warm, wear it over lighter wash jeans. The sky blue really pops, and the grey side is easy with neutrals or a pair of colorful shorts. A perfect Spring vacation piece.
Fit Tip: The fit is easy, with plenty of room for most every gent. Size down for a trimmer fit.
Alternatives: There are a ton of other great colors through the ‘shop it’ button, too, and you may just want to stock up.

6. Why is it a Find? This Peter Millar zip front vest easily works for any, and every, season. The quilted front stitching gives it a Winter-right feel, yet the cotton and silk blend fabric of the fleece is light enough to work for any cool Spring/Summer evening. The light grey color is always an ideal transitional color, working with dark and light colors, alike.
Wear it with: Now: Wearing this vest over a button up shirt and sweater has a rugged look and adds a bit of stylish warmth, too.
Later: The light color looks great with all the pale neutrals in your warm weather wardrobe, and makes for an easy outdoor layer – even with shorts.
Fit Tip: The fit is modern with a slightly closer to the body look for an updated look in your normal size.
Alternatives: Barbour’s navy and dark grey vest is another great option.

7. Why is it a Find? Peter Millar’s hybrid piece serves as both a zip-up cardigan now and an easy, lightweight jacket in the Spring and Summer. The black quilted front is a sporty contrast to the cotton knit sleeves and back, giving it a distinctive and modern look that can be worn to the office or on weekends.
Wear it with: Now: With any button up shirts or long sleeve t-shirts, it’s a stylish layer that looks smart paired with cotton pants or jeans.
Later: Treat it as a lightweight jacket that can be worn with all of your casual outfits.
Fit Tip: The fit is modern, with a slightly closer to the body look that gives it a polished appearance on most every gent.
Alternatives: There is a fantastic blue option through the ‘shop it’ button, too.

8. Why is it a Find? Billy Reid gives this shawl collar sweater, a seemingly Winter style, a modern attitude and transitional weight by using a pique cotton fabric. Brilliant and just downright cool. It works as an indoor layering piece over button up shirts and t-shirts, and as an extra layer for cooler Spring days and Summer evenings.
Wear it with: Now: Wear it now layered over a long sleeve heather grey t-shirt or dark pattern button up shirts with dark pants for a perfect night out or casual office day look.
Later: Brighten it up in the warmer weather with a white t-shirt and any lighter color pants. You can even throw it on with shorts.
Fit Tip: The fit is modern with a closer to the body fit that works on most every gent. Size up for an easier fit.
Alternatives: If you prefer a cardigan style, this grey Jason Scott sweater is for you.

9. Why is it a Find? This merino wool sweater from Michael Kors has a washed finish and contrast trim to give it a bit of a laidback vibe, so it can easily transition into more casual Spring wear once the Winter is done. Zoom in through the ‘shop it’ button to check out the cool seam details – just like the favorite part of your perfectly broken-in jeans.
Wear it with: Now: The washed blue color has an almost denim look to it, which is great with any of your cotton pants and patterned button up shirts.
Later: On a cooler evening, the blue color looks great with white, stone and tan. And it’s a shade of blue that acts as a neutral, so you can even pair it with some Spring colored cotton pants.
Fit Tip: The fit is modern for a lean, but not skinny, fit. Size up for a looser fit.
Alternatives: It is also available in a cool shade of dark purple through the ‘shop it’ button.

10. Why is it a Find? Robert Graham is known for his interesting use of color and pattern combinations to create unique sport shirts that has solidified our big fan status for years. This lime and turquoise combination adds a Spring feel, reflecting trend colors of the new season that you can start wearing now. The contrast trim on the collar and cuffs, curved hem, and spread collar show off the high-quality the brand is known for.
Wear it with: Now: Let this shirt be a subtle pop of color, poking out from under a navy or charcoal grey sweater. With jeans and khakis, it makes an easy casual office or weekend outfit.
Later: Show off the awesome color by wearing it on its own with the sleeves rolled up, and paired with jeans and khakis.
Fit Tip: Robert Graham has a modern fit, with room in the chest and body for a comfort in your normal size.
Alternatives: There is also a blue/purple color combination through the ‘shop it’ button.

11. Why is it a Find? A solid button up continues to be an current look for the season ahead, and Brooks Brothers uses a rich shade of blue to ensure you can wear it any time of year.
Wear it with: Now: The deep blue color is really good-looking under pattern wool sport coats. And the button down collar looks just as good popping out from under any sweater in your closet.
Later: The deep shade of blue has a subtle brightness to it that keeps it from being too somber for the warmer months. So roll up those sleeves and pair it with jeans, khakis, or shorts.
Fit Tip: This shirt comes in a fit for every gent. Madison is the classic gentleman’s fit Brooks Brothers is known for; Regent is the modern mid-sized fit that isn’t too trim; and, Milano is the slim, contemporary fit.

12. Why is it a Find? Gingham checks continue to be a staple for gents, and this Zachery Prell button up uses a graphic and timeless navy and white combination that will serve you well no matter the temperature.
Wear it with: Now: The navy blue color works well under any of your Winter sweaters, especially those greys, olives, navys, and black. The neutral palette and 100% high quality cotton pairs well with with jeans, khakis and corduroy pants alike.
Later: The soft cotton and versatile colors work just as well with all of your tan, stone and white bottoms.
Fit Tip: It is a contemporary, trimmer fit that gives it a polished appearance, and ensures it won’t bunch up under a sweater.
Alternatives: If you prefer an easier fit, this Robert Graham gingham shirt is a great option.

13. Why is it a Find? Whether you are following the continuing athleisure trend, of just enjoy a comfortable go-to on the weekends, a zip-up hoodie is a key piece in every gent’s weekend wardrobe. And Everlane’s is one of the best. The all-cotton French terry fabric has natural wicking properties, and a dry hand that keeps getting softer with every wear.
Wear it with: Now: Wear it with jeans, layered over a flannel shirt or long sleeve t-shirt for the cold weekend days. And, of course, it is also great to throw on after a good work out at the gym or with Everlane's coordinating sweatpants that are street-wear ready.
Later: As the weather warms up, you’ll continue wearing it with jeans or to the gym, but you’ll also get plenty of use out of it with your shorts and swim trunks once the sun goes down.
Fit Tip: The fit is contemporary, ensuring it won’t look sloppy. Size up for an easier fit.
Alternatives: We are featuring the perfectly washed shade of black, and it also comes in a neutral heather grey that has contrasting white trim through the ‘shop it’ button. Both options add a subtle hint of style to a go-to basic, so you can wear it beyond the couch or gym with confidence.

14. Why is it a Find? Jeans are a year round staple, and getting a pair in a super soft cotton twill neutral – like these Canteen olive ones from Joe’s Jeans - ensures they’ll work for those casual looks, but can also hold up to tailored office outfits on less formal days, too. The garment dyed cotton has just the right amount of whiskering and hand sanding to add a modern feel, without over-the-top attitude.
Wear it with: Now: Pair them with sweaters, long sleeve button up shirts, and a pattern wool sport coat or classic navy blazer for a work-ready look that will keep you looking stylish all the way through dinner. For a modern, casual look, switch out that jacket or sweater for a zip-up hoody, and add a cool pair of sneakers.
Later: The neutral color and super soft, mid-weight fabric is just right for Spring’s brighter color button up shirts and cotton sweaters. And they have just enough polish to hold up to your cotton sport coats, too.
Fit Tip: The Brixton fit is Joe’s most popular fit. It is modern with a narrower - but not skinny - straight leg, and enough room in the seat and thigh for most every gent.
Alternatives: It is also available in few more ideal neutrals through the “shop it” button. This is a good one to stock up on.

15. Why is it a Find? The oiled leather of these Trask chukka boots has a rugged, distressed finish that give them a perfectly broken-in look. The Vibram sole has endurance for any kind of weather, giving these every stylish shoes an appropriately functional finish.
Wear it with: Now: Wear them now with jeans, khakis and corduroys in inclement weather.
Later: This shade of brown is also great with jeans and lighter Spring shades of cotton twill pants.
Fit Tip: You may find some reviews that say these shoes may run a bit small, but, our experience is that they fit true to size for most gents.
Alternatives: These shoes come in several neutrals from black and navy to shades of brown and tan.