Fall Flashback: A Look at Our Favorite Timeless Fall Looks and How to Get Them!

Over the last five years, we have seen trends come and go. But, as we look back at some of our favorite editorials, we noticed that many of our models really nailed it with classic, timeless style. Now that the weather is cooling down and readers are looking for fall style inspiration, we identified some of our favorite timeless fall looks and searched the Internet to find items similar to those the models wore in past years. You may not be able to recreate the same exact look…but we can get ya darn close.



The varsity jacket is an American classic that can be styled to suit a variety of preferred aesthetics: heritage, urban hipster, boho, hip-hop chic, etc. Here, Ariel Speedwagon modeled a casual ivy look styled by BKLYN Dry Goods for dapperQ.

Get the look: Varsity jacket (similar by WeSC at Nordstrom Rack, $39; Faze apparel at Karmaloop, $94; Denim and Supply Ralph Lauren at Macys, $145; and Polo at Destination XL $185). Jeans (similar by Old Navy Loose-Fit, $36; Gap Boyfriend [we know, we know] fit, $80). Flannel (similar by Aeropostale Long Sleeve Plaid Woven Shirt, $22.25; Merona Flannel Shirt at Target, $25; Alaskan Guide Shirt at Filson, $98). Bow-tie (similar by Five Dollar Friday at Etsy, $5).



Power clashing is a delicate, balanced art form that can quickly go wrong. Ace’s expert eye for power clashing is seen in this outfit that blends unexpected patterns, colors, and textures to create a tailored fall look that is effortlessly stylish.

Get the look: Blazer (similar Flynt Bueller herringbone blazer at Nordstrom Rack, $160; Big & tall herringbone sport coat at Jos A Bank,$134). Button-down (similar Croft & Barrow striped button-down at Kohls, $20). Knit necktie (similar J-crew knit necktie, $69.50). Pants (similar H&M plaid slacks, $25; Plaid Highland pant at Bonobos, $118). Pocket square (similar OTAA paisley pocket square, $13.35). Hat (similar Goorin Brothers felt fedora, $54).



LK Weiss, style blogger at Jack Tar 207 and owner/designer at The Portland Designer, has perfected the stylish laid-back woodsman trend that is so popular in heritage sportwear today. Her ensemble is a good option for those who want to look put together in cold weather, but are not fans of dressing up or the traditional dandy look, what with all the restrictive neck ties and tailored tweed coats. And, the outfit is actually functional and you can do stuff in it, like hike, without worrying about ruining your dress clothes. The swagged out boots and power clashing flannel/striped under-shirt give a jolt of fashion-forward style to what would be an otherwise ordinary sweater/jeans combo.

Get the look: Flannel jacket (similar by Field & Stream at Khols, $60; Fleece-lined flannel shirt at LL Bean, $69). Sweater (similar Croft & Barrow gray sweater at Khols, $9, originally $45; Forever 21 waffle knit sweater, $17.80;  Croft & Barrow heavyweight cable sweater at Khols, $33). Striped crew undershirt (similar Striped Henley at American Eagle, $25). Boots (similar Carolina boot at Boot Barn, $100; Bell steel-toe boot at Wolverine, $114).


Tuesday 1

The jean jacket is a wardrobe staple, perfect for any season. Here, S.F. rocks a layered style for our Seven Days of Dapper series. S.F. loves layers because it is often super cold in her office, and outfits like these allow her to be prepared for temperature swings.

Get the look: Denim jacket (similar at Old Navy, $35). Cardigan (similar Tommy Hilfiger Cable-Knit Argyle Cardigan at Macy’s, $79.50; Croft & Barrow at Kohl’s, $25). Button-down (similar Gingham Dress Shirt at Brooks Brothers, $45). Khaki jeans (similar Celebrity Pink Khaki Wash Jeans at Macy’s; $30). Oxford shoes (similar Dirty Laundry at Shoes.com, $49). Bag (similar Fossil Estate Document Bag, $130). Aviator sunglasses (similar Forever 21 Over-sized Aviators, $5.80).

Blake 4

Qwear contributor and style blogger Blake Calhoun demonstrates that jeans can be both casual and fashion forward in her Seven Days of Dapper submission to dapperQ. She scored this tweed sport coat for $7 at Goodwill! We highly recommend searching thrift stores for blazers and sport coats because, not only are they inexpensive, but you can find vintage finds and tailor them to your liking.

Get the look: Tweed sport coat (similar by Gap, $110 + 30% off limited time). Jeans (similar by Old Navy, $29.50). Button-down (similar by Saddlebred at Belk, $19.99). Green V-neck sweater (similar by Topman at Nordstrom, $55). Suede oxford shoes (similar by Eastland Bucksport at Kohl’s, $80). Tie (similar by Tommy Hilfiger, $35).

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