Elena Gilbert’s wardrobe moves between layered henleys and lace camis, block-heel ankle boots that hold up through long days, and structured jackets that balance softer fabrics underneath.
The best choice depends on whether you want the henley and jacket looks for errands, the sundress for warmer days, or layered camis when you need something in between.
Dark denim anchors most of these looks, and layering a V-neck over white lace opens up the neckline without adding bulk at the waist.
1. Elena Gilbert’s Boots (Episodes 5×02 and 5×12)
The heel sits low enough to walk in all day but adds structure that sneakers or flats cannot match.
A block heel distributes weight better than a stiletto, so these work for running errands or standing through a party.
The shaft stops at the ankle, which keeps them light in warmer months and easy to layer under jeans or over tights when it gets cold.
Look for smooth leather rather than distressed finishes. The cleaner the surface, the more occasions the boot can cover.
2. Elena Gilbert’s Jacket (Episode 4×18)
A brown leatherette moto jacket brings texture without the cost or upkeep of real leather.
The asymmetric zip and notched lapels give it the same edge as the genuine article, but synthetic materials hold up better in rain and wipe clean faster.
The stiffness of the jacket balances softer fabrics underneath, and the cropped length keeps it from overwhelming a high-waisted bottom.
Leatherette wrinkles less than leather and stays flexible in cold weather. If the material feels too shiny, a quick rub with a damp cloth dulls the finish slightly.
3. Elena Gilbert’s Sundress (Episode 5×02)
The shorter hem keeps it casual, and the delicate print reads as feminine without looking overly dressy.
Tie-front details let you adjust the neckline height and fit, which matters when you want coverage for daytime or a slightly lower cut for evening.
The thin straps keep your shoulders cool but offer less support, so a strapless or adhesive bra works better than going without if you need one.
Pair it with sandals for errands or ankle boots when the temperature drops at night.
4. Elena Gilbert’s Rib and Lace Cami (Episode 3×19)
The ribbed knit has structure, and the lace underneath softens the line without adding bulk.
Button the top all the way or leave it open depending on how much lace you want to show. The ribbing holds its shape better than a plain knit, so the top does not stretch out after a few wears.
The camisole can stand alone in summer or layer under cardigans and jackets when the seasons change. Both pieces wash easily and dry flat.
5. Henley Top and Dark Flare Jeans
A fitted red henley with short sleeves and dark blue flared jeans make up the silhouette Elena wears most often. The henley buttons partway down, so you control the neckline, and the short sleeves keep it from looking too relaxed.
Flared jeans balance the fitted top and add movement without extra fabric at the waist.
Dark denim in a heavier weight holds the flare better than lighter washes, and the length should hit just above the floor in flats or boots.
A black leather jacket or a layered necklace finishes the look. The jacket keeps the proportions sharp, while the necklace adds detail if you skip the outer layer.
6. Purple Long Sleeve Over Lace Cami
Purple sits between red and blue, so it flatters more skin tones than either one alone.
This V-neck long-sleeve shirt layered over a white lace camisole keeps the color grounded with a soft underlay that shows at the neckline and hem.
The V-neck draws the eye down and elongates the torso, which works well if you have a shorter frame or want to balance wider hips.
The lace camisole adds texture without competing for attention, and the white keeps the purple from reading too heavy.
Dark denim anchors the outfit and lets the purple stay the focal point. A brown or black boot finishes it cleanly.
7. Casual Zip-Up Hoodie and Jeans
A zip-up hoodie in purple keeps the outfit casual but not sloppy, especially when paired with dark denim and a long pendant necklace.
The zip lets you adjust how much of the shirt underneath shows, and leaving it open a few inches balances the fit.
Hoodies with a slimmer cut through the body layer better under jackets and avoid bulk at the waist. Dark denim in a straight or slight flare anchors the relaxed top and keeps the proportions clean.
The pendant draws the eye down and fills the open neckline without competing with the hoodie’s color.
8. Layered Pink V-Neck and Cami
Soft pink over white lace lightens the layered look compared to deeper jewel tones.
The pink V-neck sits close to the body, so it does not add bulk over the camisole, and the lace shows just at the neckline and hem.
Pink in a warm peach undertone flatters yellow-based skin tones, while cooler pinks work better with pink or neutral undertones. The V-neck elongates the torso and keeps the layers from sitting too high at the collarbone.
This combination works with light or dark denim, and the white camisole keeps the pink from overwhelming the outfit.
9. Ribbed Short-Sleeve Henley and Denim
Ribbing holds the shape of the henley better than jersey knit, and the button placket lets you adjust the neckline.
Grey reads as neutral but has more warmth than black, so it pairs easily with both cool and warm denim washes.
The short sleeves keep it from feeling too covered, and the fitted cut through the body tucks cleanly into jeans or sits smoothly when left out.
A shoulder bag in black or brown leather finishes the silhouette without adding pattern or competing colors.
Blue denim in a medium wash balances the grey without washing it out.
10. Layered Sage Long Sleeve and Flares
Sage green sits between grey and olive, so it works as a neutral that still registers as color. The sage over white stops it from feeling too earthy, and the white underlay opens up the neckline with some contrast.
The long sleeves make this a fall or early spring outfit, and the soft green pairs with dark denim without clashing.
Brown boots or sandals finish the look without pulling attention from the layering. Black works too, but brown ties the earthy green together.
11. Layered Blue V-Neck and Flared Jeans
Dark blue on dark blue would flatten the outfit if not for the white tank underneath. The tank breaks up the solid color and shows at the neckline, which keeps the layers distinct.
A short-sleeve V-neck over a tank top works in warmer months when a long sleeve feels too heavy but bare arms seem too casual.
The flared jeans in the same blue family keep the outfit cohesive, and sneakers keep it grounded for daytime.
This layering works with any color on top, but matching the jeans and the V-neck in similar tones simplifies the silhouette.
12. Leather Jacket and Purple Top
Black leather softens purple without turning the outfit too dark, and the contrast keeps both pieces distinct. The jacket adds structure to the looser fit of the purple top, and the flared denim balances the heavier black leather on top.
A purple handbag ties the top and accessories together without matching too closely. The lighter denim keeps the outfit from feeling too heavy in fall, and the jacket works as an outer layer when the temperature drops.
Brown warms the light denim, while black matches the jacket.
13. Maroon Henley and Jeans
Maroon darkens red without crossing into brown, so it works through fall and winter without looking seasonal.
Layering it over white lace keeps the maroon from sitting too heavy, and the lace shows at the neckline and cuffs to lighten the silhouette.
The henley buttons partway down, which lets you adjust how much lace is visible. A full button keeps it covered for daytime, and leaving the top button open adds texture at the collarbone.
Blue jeans in a medium to dark wash balance the maroon without competing for attention, and the lace ties the outfit together without adding another color.
14. Brown Suede Blazer and Denim
Suede adds texture without the shine of smooth leather, and brown works with more denim washes than black. The blazer structure balances a looser white button-down and keeps the outfit from reading too casual.
Suede scratches and stains easier than leather, so this works best indoors or in dry weather. A suede brush lifts surface marks, but water leaves permanent spots.
Dark denim grounds the lighter brown and white, and the blazer length should stop at the hip to avoid shortening the leg line. A brown or tan boot matches the suede, while black boots contrast without clashing.
